Name: 22255-22-7|(E)-1,3-Dimethoxy-5-(4-methoxystyryl)benzene|98%
Brand: Ambeed
SKU: A111602
Price: 5.0 USD
Availability: InStock
Rating: 92 (28 reviews)

1
[ 908094-01-9 ]
[ 501-36-0 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	In methanol; diethyl ether at 10℃; for 24h;
	In diethyl ether
	In diethyl ether at 0℃;

Reference： [1]Fronza, Giovanni; Fuganti, Claudio; Serra, Stefano; Cisero, Marco; Koziet, Joseph [Journal of agricultural and food chemistry, 2002, vol. 50, # 10, p. 2748 - 2754]
[2]Ingham,J.L. [Phytochemistry, 1976, vol. 15, p. 1791 - 1793]
[3]Chaudhar, M.; Jain, G. K.; Sarin, J. P.; Khanna, N. M. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 11, p. 1163 - 1164]
[4]Anjaneyulu, A. S. R.; Raghava Reddy, A. V.; Reddy, D. S. K.; Ward, R. S.; Adhikesavalu, D.; Cameron, T. Stanley [Tetrahedron, 1984, vol. 40, # 21, p. 4245 - 4252]
[5]Cheong, Ho; Ryu, Shi-Yong; Kim, Kyeong-Man [Planta Medica, 1999, vol. 65, # 3, p. 266 - 268]

2
[ 22255-22-7 ]
[ 2880-58-2 ]
trans-6-Methoxy-2-(4'-methoxyphenyl)-3-(3',5'-dimethoxyphenyl)-2,3-dihydro-5-benzofuranol [ No CAS ]
[ 156413-03-5 ]
4,2',6'-Trimethoxy-4'-[(E)-2-(4-methoxy-phenyl)-vinyl]-biphenyl-2,5-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 62% 2: 13% 3: 8%	With tin(IV) chloride In dichloromethane at -78℃;
1: 52% 2: 8% 3: 13%	With tin(IV) chloride In dichloromethane at -78℃;

Reference： [1]Engler, Thomas A.; Draney, Bill W.; Gfesser, Gregory A. [Tetrahedron Letters, 1994, vol. 35, # 11, p. 1661 - 1664]
[2]Engler, Thomas A.; Draney, Bill W.; Gfesser, Gregory A. [Tetrahedron Letters, 1994, vol. 35, # 11, p. 1661 - 1664]

3
[ 22255-22-7 ]
[ 611-68-7 ]
trans-6-Methoxy-2-(4'-methoxyphenyl)-3-(3',5'-dimethoxyphenyl)-4-methyl-2,3-dihydro-5-benzofuranol [ No CAS ]
(E)-2-(3',6'-Dihydroxy-4'-methoxy-1'-methylphenyl)-3,4',5-trimethoxystilbene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 3% 2: 78%	With tin(IV) chloride In dichloromethane at -78℃;
1: 3% 2: 78%	With tin(IV) chloride In dichloromethane 1.) -78 deg C, 10 min, 2.) -78 deg C, 15 min;
1: 58% 2: 9%	With tin(IV) chloride In dichloromethane at -78℃;

1: 58% 2: 9%

With tin(IV) chloride In dichloromethane 1.) -78 deg C, 10 min, 2.) -78 deg C, 30 min;

Reference： [1]Engler, Thomas A.; Draney, Bill W.; Gfesser, Gregory A. [Tetrahedron Letters, 1994, vol. 35, # 11, p. 1661 - 1664]
[2]Engler; Gfesser; Draney [Journal of Organic Chemistry, 1995, vol. 60, # 12, p. 3700 - 3706]
[3]Engler, Thomas A.; Draney, Bill W.; Gfesser, Gregory A. [Tetrahedron Letters, 1994, vol. 35, # 11, p. 1661 - 1664]
[4]Engler; Gfesser; Draney [Journal of Organic Chemistry, 1995, vol. 60, # 12, p. 3700 - 3706]

4
[ 22255-22-7 ]
[ 501-36-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With boron tribromide In dichloromethane at 0 - 30℃;
99%	With boron tribromide In dichloromethane at 0 - 20℃;
98%	With aluminum (III) chloride; sodium sulfate; triethylamine In chlorobenzene at 0 - 115℃; for 6.5h; Inert atmosphere;	1.1; 2.1; 3.1 1) Add 90ml of chlorobenzene to a 500ml dry four-necked flask, and add 39.5g of anhydrous aluminium trichloride, after adding, nitrogen replacement twice,After that, nitrogen gas was continuously introduced, the temperature was controlled at 0-30 ° C, and 36 g of triethylamine was slowly added dropwise.Add triethylamine dropwise to control the temperature from 0-30 ° C. After dripping, keep for 30 minutes.16g of anhydrous sodium sulfate and 20g of 3,4’,5-trimethoxystilbene were added. After the addition was completed, nitrogen was replaced twice, and then nitrogen was continuously passed through.The temperature of the reaction solution was raised to 110-115 ° C, and the temperature was maintained for 6 hours.After the reaction is completed, the reaction solution is cooled to 30-40 degrees and added to ice water.Control the temperature of the water phase system ≤ 30 ° C. After the addition, stir for 2 hours and filter.After drying, 16.5 g of resveratrol was obtained with a yield of 98%.

96%	With boron tribromide In dichloromethane at -78 - 20℃;
95%	With boron tribromide In dichloromethane at -30 - 20℃;
92%	With boron tribromide In dichloromethane at -78℃; for 2h;	3 4.3. (E)-5-(4-Hydroxystyryl)benzene-1,3-diol (resveratrol, 1) To a solution of 4 (270 mg 1 mmol) in 20 mL of anhydrous dichloromethane at -78 °C, 4.5 mL of a solution 1M of boron tribromide in dichloromethane was added dropwise. 37 The resulting solution was magnetically stirred at -78 °C for 2 h. After this time, the solution was let to reach room temperature, and then it was poured onto brine. The organic phase was separated and the aqueous phase was extracted with acetonitrile (430 mL). The combined organic phases were dried with anhydrous MgSO4, filtered and the solvent was removed at reduced pressure. The resulting product was purified by medium pressure column chromatography (Combiflash) using a silica gel column and a mixture hexane/ethyl acetate 1:1 as eluent, leading to a colourless solid (210 mg, 92%) characterised by NMR; 38, 39 [Found C 73.35 H 5.36 requires C, 73.67, H, 5.30]; GC conditions: Agilent J&W CG ColumnHP-5 30 m25 mm*0.25 mm, helium as carrier gas, 230 °C injector T, 250 °C detector T, 20 psi head column pressure, 2 mL min-1 flux, oven temperature program 70 °C (1 min), 20 °C min-1, 250 °C (7.5 min), retention time 12.9 min; δH (400 MHz, acetone-d6) 7.30-7.27 (m, 2H), 6.88 (d, 1H, J=16.3 Hz), 6.75 (d, 1H, J=16.3 Hz), 6.71-6.69 (m, 2H), 6.41 (d, 2H, J=2.2 Hz), 6.14 (d, 1H, J=2.2 Hz), 3.64 (s, 1H), 2.88 (s, 2H); δC (100.6 MHz, acetone-d6, APT) 159.0 (C), 158.2 (C), 140.9 (C), 130.0 (C), 129.1 (CH), 128.7 (CH), 126.6 (CH), 116.4 (CH), 105.7 (CH), 102.7 (CH); m/z (EI) 228 (M+).
91%	With boron tribromide In dichloromethane at 20℃; Inert atmosphere; Cooling;
90%	With boron tribromide In dichloromethane at 20℃; for 2h;
90%	Stage #1: 3,5,4'-trimethoxy-trans-stilbene With aluminum (III) chloride; triethylamine In chlorobenzene at 0 - 80℃; for 10h; Stage #2: With water In chlorobenzene at 0℃; for 1h;	1 56.2 g of triethylamine (555.4 mmol) are introduced into 20 ml of chlorobenzene in a three-necked round-bottomed flask. A nitrogen atmosphere is applied, the reaction medium is cooled to 0-50C and 45 g of anhydrous aluminium chloride (337.5 mmol) are added in small fractions over 30 min. The medium is maintained at ambient temperature for 30 min with stirring and is then brought to 600C, where this temperature is maintained for 1 h. 10 g of (E)-3,5,4'-trimethoxystilbene (37 mmol) dissolved in 20 ml of chlorobenzene are subsequently added in 1 h. The mixture is maintained at 600C with stirring for 4 h and then at 800C for 4 h. It is brought back to ambient temperature, separation by settling is carried out and the upper chlorobenzene phase is recovered. The lower phase is slowly added to 100 g of a 50/50 ice/water mixture. The medium is kept stirred for 1 h and is extracted several times with ethyl acetate.The combined organic phases are washed with water and concentrated to result in 7.6 g of (E)-resveratrol, i.e. a crude yield of 90%. The crude product is dissolved in ethanol at 600C and resveratrol is precipitated by addition of water in order to obtain 6 g of precipitate exhibiting a melting point of 262-264°C.The proton and 13C NMR spectra are in agreement with the structure of (E)-resveratrol.
86%	With boron tribromide In dichloromethane at -78℃; for 0.5h;
86%	With boron tribromide In dichloromethane at -78℃; for 0.5h;	1 To a solution of 4-methoxy-benzylthphenylphosphonium bromide (12.5 g) in anhydrous tetrahydrofuran (200 ml_) at -78 0C was added n-butyllithium (2.44 M, 1.0 equiv), and the resulting red solution was stirred under argon for 2-4 h. A solution of 3,5-dimethoxybenzaldehyde (4.5 g) in tetrahydrofuran was added dropwise over 30 min and the mixture stirred for 6-15 h. The resulting cream suspension was poured into water and extracted with dichloromethane. The organic phase was washed with water, and removal of the solvent in vacuo afforded an oil. The oil was separated by flash column chromatography (49:1 hexane/ethyl acetate). The cis-stilbene eluted first as a clear oil followed by the trans isomer as a colorless solid or oil. Overall yield: 91 %. To a solution of the trans isomer (3.1.g) in anhydrous dichloromethane (150 mL) at -78 0C was added (dropwise) boron tribromide (1.0 M, 34.5 mL), and the resulting red solution was stirred under argon for 30 min. The solution was poured into water and extracted with dichloromethane. The organic phase was washed with water, and removal of the solvent in vacuo afforded an oil, which was separated by flash column chromatography (1 :1 hexane/ethyl acetate) to afford a colorless solid (2.26 g, 86%): mp 260 0C.
85%	With boron trichloride; tetra-(n-butyl)ammonium iodide In dichloromethane at 0℃; for 6h;
85%	With boron trichloride; tetra-(n-butyl)ammonium iodide In dichloromethane at 0℃;
85%	With aluminum (III) chloride; diisopropylamine In toluene at 110℃; for 4h; Inert atmosphere;
84%	With boron tribromide
83%	With boron tribromide In dichloromethane at -10 - 20℃; for 3h; Inert atmosphere;	2. General procedure for demethylation of stilbene 4 General procedure: In 6 mL of anhydrous methylene chloride, 200 mg of methoxy-stilbene 4 (0.74 mmol) was dissolved and cooled to -10 °C under argon. BBr3 (0.6 mL, 6.3 mmol, 17% in dichloromethane) in anhydrous methylene chloride (5 mL) was added slowly, and the mixture was allowed to reach to room temperature for 3-24 h. Water was added to destroy the excess BBr3, and the mixture was extracted twice with ethyl acetate. The organic extracts were washed with water and brine and dried, and the solvent evaporated. The crude product was purified by column chromatography on silica gel (20% EtOAc in hexane) yielding resveratrol and derivatives 1.2.1. 5-[(E)-2-(4-Hydroxyphenyl)ethenyl]benzene-1,3-diol (resveratrol, 1a).16Pale brown solid; yield: 141 mg (83%); mp 259-260 °C (lit.16 256-259 °C) ; Rf = 0.2 (hexanes-EtOAc, 1:1); 1H NMR (400 MHz, acetone-d6): δ=8.56 (s, 1H, OH), 8.28 (s, 2H, OH), 7.40 (d, 2H, J=8.5 Hz, H-2’, H-6’), 7.00 (d, 1H, J=16.3 Hz, H-β), 6.86 (d, 1H, J=16.3 Hz, H-α), 6.82 (d, 2H, J=8.5 Hz, H-3’, H-5’), 6.52 (d, 2H, J=2.0 Hz, H-2, H-6), 6.25(s, 1H, H-4); 13C NMR (100 MHz, acetone-d6): δ=159.6, 158.1, 140.8, 129.9, 129.0, 128.7, 126.8, 116.4, 105.6, 102.6.
83%	With boron tribromide In dichloromethane at -78℃; for 1h; Schlenk technique; Inert atmosphere;
82%	With boron tribromide In dichloromethane at 0 - 20℃;
80%	With boron tribromide In dichloromethane at -30 - 20℃; for 2h; Inert atmosphere;
75%	Stage #1: 3,5,4'-trimethoxy-trans-stilbene With aluminum (III) chloride; tributyl-amine at 20 - 100℃; for 8h; Stage #2: With water at 0 - 5℃; for 3h;	2 4.5 g of anhydrous aluminium chloride (33.7 mmol) are introduced, under a nitrogen atmosphere, at ambient temperature and with stirring, into 10.37 g of tributylamine (56 mmol) in a three-necked round-bottomed flask. The medium is brought to 600C and is maintained at this value for 4 h. 1 g of (E)-3,5,4'-trimethoxystilbene (3.7 mmol) is then introduced and the reaction medium is brought to 800C for 2 h and to 1000C for 2 h. It is brought back to ambient temperature and then 10 g of a 50/50 water/ice mixture are added. It is maintained at 0-50C with stirring for 3 h and extracted 4 to 5 times with 10 ml of methyl ethyl ketone. The combined organic phases are washed with 10 ml of a saturated aqueous sodium bicarbonate solution and then with 10 ml of water. After concentrating the organic phase, an HPLC quantitative determination (external calibration) gives an (E)-resveratrol yield of 75%.
74%	With boron tribromide In dichloromethane at -30 - 28℃; Schlenk technique;
73.4%	Stage #1: 3,5,4'-trimethoxy-trans-stilbene With aluminum (III) chloride; triethylamine at 50 - 100℃; for 4.5h; Stage #2: With water In ethanol at 20 - 75℃; for 3.5h;	5 5 g of (E)-3,5,4'-trimethoxystilbene (18.5 mmol) are introduced into 20 g of triethylamine (197.6 mmol) in a 100 ml three-necked round-bottomed flask. The mixture is heated to 500C under a nitrogen atmosphere and 16 g of anhydrous aluminium chloride (120 mmol) are added in small fractions over 30 min at this temperature. The reaction medium is then brought to 800C for 2 h and then to 1000C for 2 h. It is cooled to approximately 75°C, 10 ml of anhydrous ethanol are slowly added and then, at this temperature of 75°C, 50 ml of water are added in 30 min. The reaction medium is then cooled to ambient temperature, at which it is maintained for 3 h, and the medium is extracted with 1 times 35 ml and 3 times 30 ml of methyl ethyl ketone. The combined organic phases are washed with 30 ml of water, then with 30 ml of a saturated sodium bicarbonate solution and with 30 ml of water. After concentrating the organic phases, 15 ml of absolute ethanol are added, the mixture is heated to reflux and then 46 g of water are added over approximately 1 h, still at reflux. The mixture is cooled down to ambient temperature and left stirring for 3 h. The precipitate is filtered off and washed on the filter with 9 g of a water/ethanol mixture (80/20 by weight).After drying at 400C under vacuum for 24 h, 3.1 g of (E)-resveratrol are obtained, i.e. a yield of 73.4%.The HPLC and NMR analyses are in agreement with the structure of (E)-resveratrol.
70%	Stage #1: 3,5,4'-trimethoxy-trans-stilbene With aluminum (III) chloride; <i>N</i>,<i>N</i>-dimethyl-aniline In toluene at 70 - 80℃; for 2h; Stage #2: With hydrogenchloride; water In toluene at 20℃;	14 EXAMPLE 14; General procedure for the preparation of Stilbenols: Poly methoxystilbenes were prepared by Emmons-Horner coupling of the corresponding methoxybenzyl phosphonate with methoxyaryl aldehyde. Poly methoxylstilbenes were demethylated using a general procedure. The following procedure involving 3,4',5-trimethoxystilbene is applicable to all similar substrates. N,N-Dimethylaniline (27 g, 0.223 mol) was taken in a 250 mL round bottomed flask under dry nitrogen atmosphere. Anhydrous aluminium chloride (30 g, 0.225 mol) was added slowly with stirring. Dry toluene (25 mL) was added and stirred for 10 min. This was heated to 70-80° C. 3,4',5-tirmethoxystilbene (10 g, 0.037 mol) dissolved in toluene (50 mL) was dropped into the reaction mixture over a period of 5-10 min. The reaction mixture was stirred at 70-80° C. for 2 h. This was cooled to room temperature and dropped into ice water (100 mL) slowly with stirring. Toluene layer was separated. The aq. layer was acidified with 10% hydrochloric acid, and extracted with ethyl acetate (3×100 mL), which was dried over anhy. sodium sulfate, filtered, and the solvents stripped off under vacuum to get the crude resveratrol. This was purified by column chromatography on silica gel using ethyl acetate-hexane as eluent to get pure resveratrol (5.9 g, 70% yield) as white solid. The physical and spectral data for the starting material 3,4',5-trimethoxystilbene:Mpt: 42.0-44.0° C.(Solvent CDCl3, 300 MHz proton):δ 3.83 (s, 6H), 3.86 (s, 3H), 6.39 (t, J=2.4 Hz, 1H), 6.66 (d, J=2.4 Hz, 2H), 6.88-6.94 (m, 3H), 7.05 (d, J=16.2 Hz, 1H), 7.46 (d, J=9.0 Hz, 2H)13C NMR(75 MHz, CDCl3): δ 55.56, 55.59, 99.83, 104.55, 114.38, 126.78, 128.06, 128.97, 130.14, 139.93, 159.63, 161.20LC-MS: m/e 271 (M++1)The physical and spectral data for the product Resveratrol:Mpt: 265.5-267.9° C.(Solvent Acetone-d6, 300 MHz Proton): δ 6.28 (t, J=2.1 Hz, 1H), 6.55 (d, J=2.1 Hz, 2H), 6.83-6.92 (m, 3H), 7.03 (d, J=16.5 Hz, 1H), 7.43 (d, J=8.7 Hz, 2H), 8.3 (br s, 3H, -OH).13C NMR (75 MHz, Acetone-d6): δ 102.60, 105.62, 116.38, 126.75, 128.72, 129.07, 129.88, 140.86, 158.14, 159.54).LC-MS: m/e 227 (M+-1).
70%	With boron tribromide In dichloromethane at 0 - 20℃; for 5h;
70%	With boron tribromide In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;
70%	With boron tribromide In dichloromethane at 0℃; for 5h;	(E)-3',4,5'-trihydroxy-stilbene (1): BBr3 (1.38 g, 5.52 mmol) wasadded dropwise into methylated stilbene (6) (190 mg,0.745 mmol) in dry CH2Cl2 (20 mL) at 0 C, then stirred for 5 hand left at room temperature over 1 h. The mixture was pouredonto ice, and the organic layer was separated and the aqueouslayer extracted with CH2Cl2 (2 10 mL). The combined organiclayer was washed with saturated NaCl, dried over anhydroussodium sulfate and evaporated under reduced pressure to dryness.The solid was recrystallized from MeOH-CH2Cl2, to afford pureResveratrol (1) (112 mg, 70% yield) as an off-white powder; mp258-260 C.
70%	With boron tribromide In dichloromethane for 5h; Inert atmosphere; Schlenk technique;
65%	With methyl magnesium iodide In diethyl ether at 100 - 160℃;
60%	Stage #1: 3,5,4'-trimethoxy-trans-stilbene With boron tribromide In tetrahydrofuran at -20℃; Inert atmosphere; Stage #2: With methanol; sodium hydroxide for 4h; Inert atmosphere; Reflux; regioselective reaction;
56%	With methyl magnesium iodide at 100℃; for 0.5h;
56%	With boron tribromide In dichloromethane at -5 - 20℃;
54%	With methyl magnesium iodide In diethyl ether at 100℃; for 0.5h;
45%	With pyridine hydrochloride
45%	With pyridine hydrochloride at 190℃; for 4h;
42%	With pyridine hydrochloride at 190℃; for 4h;
20%	With pyridine hydrochloride for 2h; Inert atmosphere; Reflux;
20%	With pyridine hydrochloride for 2h; Reflux; Inert atmosphere;	trans-3,4',5-Trihydroxystilbene (Resveratrol) To a 250 mL round-bottomed flask equipped with a magnetic stir bar was added 8 (2.7 g, 10 mmol) and pyridine hydrochloride (10.4 g, 90 mmol, 9 equiv). A reflux condenser was equipped and the reaction mixture was refluxed for 2 h under an N2 atmosphere. Afterwards, the mixture was allowed to cool to ˜90° C. and quenched into H2O (200 mL) whereupon a purplish colored solid precipitated. The mixture was extracted with EtOAc (50 mL*3). The extracts were collected and diluted with hexanes (100 mL) and then filtered through a thin pad of silica gel to remove dark colored, polar impurities. The filtrate was evaporated in vacuo leaving an off-white solid. The crude product was slurried with HOAc and filtered to give resveratrol as a tan microcrystalline powder (450 mg, 20%), mp. 258-261° C., lit. 261° C. 1H NMR (DMSO): δ 9.59 (s, OH), 9.23 (s, 20H), 7.41 (d, J=8.9 Hz, 2H), 6.95 (d, Jab=16.3 Hz, 1H), 6.82 (d, Jab=16.3 Hz, 1H), 6.76 (d, J=8.9 Hz, 2H), 6.39 (d, J=2.0 Hz, 2H), 6.13 (t, J=2.1 Hz, 1H); 13C NMR (DMSO): δ 158.58, 157.28, 139.36, 128.15, 127.96, 127.92, 125.74, 115.61, 104.41, 101.87. Anal. Calcd for C14H12O3: C, 73.67; H, 5.30. Found: C, 73.40; H, 5.44.
	With hydrogenchloride In methanol at 20℃; for 36h;
	With boron tribromide In dichloromethane at 25 - 35℃; for 3h;
	With boron tribromide In dichloromethane at 20℃; for 1.5h;	24 Example 24; Synthesis of (E)-resveratrol:; 37.9 ml of boron tribromide (approximately 100 g, 400 mmol) are introduced into 100 ml of methylene chloride under a nitrogen atmosphere in a three-necked round- bottomed flask. The medium is cooled to approximately -200C and 10.8 g (approximately 40 mmol) of (E)-trimethylresveratrol dissolved in 20 ml of methylene chloride are introduced at this temperature over 1 h 30. The medium is allowed to return to ambient temperature with stirring and is left stirring at this temperature for 4 hours. The reaction medium is then slowly poured onto 800 g of an ice/water mixture. The medium is extracted with 325 ml and then 200 ml of MTBE and the organic phases are washed with 2 times 75 ml of a saturated sodium bicarbonate solution and then with 75 ml of water. The combined organic phases are concentrated on a rotary evaporator. The solid residue is taken up in 100 ml of methylene chloride, filtered off and dried to result in 8.1 g of crude resveratrol.The precipitate is dissolved in ethanol at 600C and precipitated by addition of water to result in resveratrol with a melting point of 262-264°C. The proton and C13 NMR spectra correspond to the expected product.
	Stage #1: 3,5,4'-trimethoxy-trans-stilbene With aluminum (III) chloride; triethylamine In dichloromethane; chlorobenzene at 0 - 80℃; for 11.25h; Stage #2: With water In dichloromethane; chlorobenzene at 0 - 5℃; for 1h;	6 5.6 g of triethylamine (55.5 mmol) are introduced into 4 ml of methylene chloride. The medium is cooled to 0-5°C and 4.5 g of anhydrous aluminium chloride (33.5 mmol) are added in small fractions over 15 min with stirring and under a nitrogen atmosphere. The reaction medium is subsequently brought to 50°C for 4 h. It is cooled and the solvent and the excess amine are concentrated at ambient temperature in order to obtain approximately 8.5 g of a slightly fuming pinkish solid formed of AICI3/triethylamine complex. 2 ml of chlorobenzene are added to the solid and the mixture is brought to 60°C. 1 g of 3,5,4'-trimethoxystilbene (3.7 mmol) dissolved in 2 ml of chlorobenzene is added at this temperature over one hour. The mixture is maintained at 600C for 4 h and then at 800C for 2 h. The reaction medium is brought back to ambient temperature and then hydrolysed by addition of 10 g of a water/ice (50/50) mixture. The temperature is maintained at 0-50C for 1 h and the medium is extracted several times with ethyl acetate. After concentrating the organic phases, the precipitate obtained is washed with 6 ml of chlorobenzene and dried under vacuum to result in 0.6 g of crude (E)-resveratrol.
	With pyridine hydrochloride at 180 - 200℃; Inert atmosphere;
47.5 g	Stage #1: 3,5,4'-trimethoxy-trans-stilbene With aluminum (III) chloride; diisopropylamine In toluene at 25 - 120℃; for 4h; Stage #2: With water In toluene at 45℃; for 0.5h;	1 Preparation of Resveratrol Using Diisopropyl Amine: Aluminium Chloride To a clean 3-necked 2 L round bottom flask equipped with a mechanical stirrer, thermometer socket and addition funnel was charged di-isopropyl amine (168.5 gms) at 25° to 35° C. To the solution aluminium chloride (222 gms) was added in lots at 25° C. to 35° C. and heated to 110° C. Reaction solution was stirred for 30 minutes and then resveratrol methyl ether solution (75 gms of resveratrol methyl ether in 300 ml of toluene) was added at 100° C. to 110° C. Reaction mass was stirred for 4 hours at 110° C. to 120° C. and then allowed to cool to 80° C. to 90° C. The reaction mass was quenched into chilled water (1050 ml) at below 45° C. and stirred for 30 minutes at same temperature. Precipitated material was filtered and washed with water (150 ml). The wet product (160 gms) was taken into a 3-necked 2 L round bottom flask and water (1125 ml) was charged at 25° to 35° C. To the mass sodium hydroxide solution (188 ml; 33.5 gms of sodium hydroxide dissolved in 188 ml water) was added and then reaction solution was washed with toluene (2×195 ml). The aqueous layer was separated out and pH was adjusted to 2 with Con HCl (71.25 ml) at 25° to 30° C. and stirred for 60 minutes at same temperature. Precipitated product was filtered and washed with water (150 ml) and the wet cake was slurred in water (750 ml) at temperature 80° to 85° C. followed by filtered and dried at 75° to 85° C. to provide the title compound. Yield: 47.5 gms. HPLC purity: 99.49%
	With pyridine hydrochloride at 190℃; for 0.833333h;	16.2gC plus 69.3g pyridine hydrochloride, react at 190 ° C for 50 minutes, pour 200ml of ice water, stir, extract with 1L ethyl acetate, separate layers, wash with water, dry with sodium sulfate, recover ethyl acetate, recrystallize with ethanol to obtain white Resveratrol.
	With magnesium; methyl iodide In diethyl ether at 45 - 190℃; Inert atmosphere;
	With boron tribromide In dichloromethane at -78℃; for 1h;	1 Deprotection of trimethyl resveratrol We followed a published with some modification.4 ()-l,3-dimethoxy-5-(4- methoxystyryl)benzene (92 mg, 340 pmol, 1.0 equiv) was dissolved in CH2CI2 (15 mL) and a solution of BBr3 (1.0 M in CH2CI2, 3.3 mmol, 3.3 mL, 9.0 equiv) was added at -78 °C. The mixture was stirred for 1 h at -78 °C. Then the reaction was allowed to warm to room temperature, H2O (25 mL) was added and the mixture was poured into H2O (25 mL). Extraction with EtOAc (3 c 25 mL), washing of the combined organic layers with H2O (25 mL), brine (25 mL), drying over MgSCb and concentration under reduced pressure gave the crude product which was purified by flash column chromatography using hexanes and ethyl acetate (v/v = 9:1) as the eluent. The target compound of resveratrol was obtained as a white solid (74 mg, 96%). NMR (600 MHz, DMSO-rfe): d 9.53 (s, 1H), 9.17 (s, 2H), 7.39 (m, 2H), 6.92 (d, J= 16.3 Hz, 1H), 6.81 (d, J= 16.3 Hz, 1H), 6.75 (m, 2H), 6.37 (d, .7= 2.1 Hz, 2H), 6.11 (t, .7= 2.1 Hz, 1H) ppm. 13C NMR (201 MHz, DMSO-rfe): d 158.5, 157.2, 139.2, 128.1, 127.8, 127.8,125.6, 115.5, 104.3, 101.7 ppm.
	With boron tribromide In dichloromethane at -78℃; for 1h;	1 Deprotection of trimethyl resveratrol We followed a published with some modification.4 ()-l,3-dimethoxy-5-(4- methoxystyryl)benzene (92 mg, 340 pmol, 1.0 equiv) was dissolved in CH2CI2 (15 mL) and a solution of BBr3 (1.0 M in CH2CI2, 3.3 mmol, 3.3 mL, 9.0 equiv) was added at -78 °C. The mixture was stirred for 1 h at -78 °C. Then the reaction was allowed to warm to room temperature, H2O (25 mL) was added and the mixture was poured into H2O (25 mL). Extraction with EtOAc (3 c 25 mL), washing of the combined organic layers with H2O (25 mL), brine (25 mL), drying over MgSCb and concentration under reduced pressure gave the crude product which was purified by flash column chromatography using hexanes and ethyl acetate (v/v = 9:1) as the eluent. The target compound of resveratrol was obtained as a white solid (74 mg, 96%). NMR (600 MHz, DMSO-rfe): d 9.53 (s, 1H), 9.17 (s, 2H), 7.39 (m, 2H), 6.92 (d, J= 16.3 Hz, 1H), 6.81 (d, J= 16.3 Hz, 1H), 6.75 (m, 2H), 6.37 (d, .7= 2.1 Hz, 2H), 6.11 (t, .7= 2.1 Hz, 1H) ppm. 13C NMR (201 MHz, DMSO-rfe): d 158.5, 157.2, 139.2, 128.1, 127.8, 127.8,125.6, 115.5, 104.3, 101.7 ppm.

Reference： [1]Li, Qiang-Qiang; Shah, Zaher; Qu, Jian-Ping; Kang, Yan-Biao [Journal of Organic Chemistry, 2018, vol. 83, # 1, p. 296 - 302]
[2]Ali; Kondo; Tsuda [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 5, p. 1130 - 1136]
[3]Current Patent Assignee: SECOND PHARMA - CN104610057, 2016, B Location in patent: Paragraph 0068-0069; 0071-0072; 0074-0075
[4]Jia, Xiaofan; Frye, Lucas I.; Zhu, Weihao; Gu, Shunyan; Gunnoe, T. Brent [Journal of the American Chemical Society, 2020, vol. 142, # 23, p. 10534 - 10543]
[5]Privat, Christelle; Telo, Joao Paulo; Bernardes-Genisson, Vania; Vieira, Abel; Souchard, Jean-Pierre; Nepveu, Francoise [Journal of agricultural and food chemistry, 2002, vol. 50, # 5, p. 1213 - 1217]
[6]Martínez, Alejandro V.; García, José I.; Mayoral, José A. [Tetrahedron, 2017, vol. 73, # 38, p. 5581 - 5584]
[7]Wagh, Ganesh; Autade, Snehalata; Patil, Pravin C.; Akamanchi, Krishnacharya G. [New Journal of Chemistry, 2018, vol. 42, # 5, p. 3301 - 3309]
[8]Shen, Zhen Lu; Zhuo, Guang Lan; Jiang, Xuan Zhen [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 11, p. 2395 - 2398]
[9]Current Patent Assignee: Weylchem (in: Internat. Chemicals Investors); INTERNATIONAL CHEMICALS INVESTORS SE - WO2009/43761, 2009, A1 Location in patent: Page/Page column 9
[10]Pettit, George R.; Grealish, Matthew P.; Jung, M. Katherine; Hamel, Ernest; Pettit, Robin K.; Chapuis, J.-Charles; Schmidt, Jean M. [Journal of Medicinal Chemistry, 2002, vol. 45, # 12, p. 2534 - 2542]
[11]Current Patent Assignee: RESVERLOGIX CORP - WO2006/45010, 2006, A2 Location in patent: Page/Page column 155
[12]Jeffery, Tuyet; Ferber, Benoît [Tetrahedron Letters, 2003, vol. 44, # 1, p. 193 - 197]
[13]Location in patent: scheme or table Gray, Erin E.; Rabenold, Lake E.; Goess, Brian C. [Tetrahedron Letters, 2011, vol. 52, # 46, p. 6177 - 6179]
[14]El-Deeb, Ibrahim Yussif; Funakoshi, Tatsuya; Shimomoto, Yuya; Matsubara, Ryosuke; Hayashi, Masahiko [Journal of Organic Chemistry, 2017, vol. 82, # 5, p. 2630 - 2640]
[15]Soiderman, Stefan C.; Schwan, Adrian L. [Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10978 - 10984]
[16]Uzura, Saori; Sekine-Suzuki, Emiko; Nakanishi, Ikuo; Sonoda, Motohiro; Tanimori, Shinji [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 16, p. 3886 - 3891]
[17]Thiel, Niklas O.; Kaewmee, Benyapa; Tran Ngoc, Trung; Teichert, Johannes F. [Chemistry - A European Journal, 2020, vol. 26, # 7, p. 1597 - 1603]
[18]Li, Kangkui; Khan, Ruhima; Zhang, Xuexin; Gao, Yang; Zhou, Yongyun; Tan, Heng; Chen, Jingchao; Fan, Baomin [Chemical Communications, 2019, vol. 55, # 39, p. 5663 - 5666]
[19]McNulty, James; Das, Priyabrata [European Journal of Organic Chemistry, 2009, # 24, p. 4031 - 4035]
[20]Current Patent Assignee: Weylchem (in: Internat. Chemicals Investors); INTERNATIONAL CHEMICALS INVESTORS SE - WO2009/43761, 2009, A1 Location in patent: Page/Page column 9
[21]Babu, Reshma; Balaraman, Ekambaram; Midya, Siba P.; Subaramanian, Murugan; Yadav, Vinita [Journal of Organic Chemistry, 2021, vol. 86, # 11, p. 7552 - 7562]
[22]Current Patent Assignee: Weylchem (in: Internat. Chemicals Investors); INTERNATIONAL CHEMICALS INVESTORS SE - WO2009/43761, 2009, A1 Location in patent: Page/Page column 11
[23]Current Patent Assignee: SAMI LABS LIMITED - US7253324, 2007, B1 Location in patent: Page/Page column 10-11
[24]Location in patent: body text Alonso, Francisco; Riente, Paola; Yus, Miguel [Tetrahedron Letters, 2009, vol. 50, # 25, p. 3070 - 3073]
[25]Location in patent: experimental part Alonso, Francisco; Riente, Paola; Yus, Miguel [European Journal of Organic Chemistry, 2009, # 34, p. 6034 - 6042]
[26]Lara-Ochoa, Francisco; Sandoval-Minero, Leticia C.; Espinosa-Pérez, Georgina [Tetrahedron Letters, 2015, vol. 56, # 44, p. 5977 - 5979]
[27]Landge, Vinod G.; Yadav, Vinita; Subaramanian, Murugan; Dangarh, Pragya; Balaraman, Ekambaram [Chemical Communications, 2019, vol. 55, # 43, p. 6130 - 6133]
[28]Alonso, Emma; Ramon, Diego J.; Yus, Miguel [Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 417 - 421]
[29]Zhang, Zhao; Zhang, Dejiang; Zhu, Longzhi; Zeng, Dishu; Kambe, Nobuaki; Qiu, Renhua [Organic Letters, 2021, vol. 23, # 14, p. 5317 - 5322]
[30]Polunin, Konstantin E.; Polunina, Irina A.; Schmalz, Hans-Guenther [Mendeleev Communications, 2002, vol. 12, # 5, p. 178 - 179]
[31]Location in patent: experimental part Smidrkal, Jan; Harmatha, Juraj; BudiSinsky, Milo; Vokae, Karel; ZIDEKc, Zdenik; Kmoniekova, Eva; Merkl, Roman; Filip, Vladimir [Collection of Czechoslovak Chemical Communications, 2010, vol. 75, # 2, p. 175 - 186]
[32]Polunin; Schmalz; Polunina [Russian Chemical Bulletin, 2002, vol. 51, # 7, p. 1319 - 1324]
[33]Malan, Elfranco; Swinny, Ewald; Ferreira, Daneel; Hall, Alida J. [Phytochemistry, 1988, vol. 27, # 7, p. 2309 - 2312]
[34]Wang, Mingfu; Jin, Yi; Ho, Chi-Tang [Journal of Agricultural and Food Chemistry, 1999, vol. 47, # 10, p. 3974 - 3977]
[35]Lu; Cai; Fang; Zhou; Liu; Wu, Longmin M. [Pharmazie, 2002, vol. 57, # 7, p. 474 - 478]
[36]Davis, Matthew C.; Parrish, Damon A.; Harvey, Benjamin G. [Organic Preparations and Procedures International, 2013, vol. 45, # 4, p. 304 - 313]
[37]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES - US8921614, 2014, B1 Location in patent: Page/Page column 5; 11
[38]Lee, Hyun Jung; Seo, Jai Woong; Lee, Bong Ho; Chung, Kyoo-Hyun; Chi, Dae Yoon [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 2, p. 463 - 466]
[39]Li, Yue-Qing; Li, Ze-Lin; Zhao, Wei-Jie; Wen, Rui-Xing; Meng, Qing-Wei; Zeng, Yi [European Journal of Medicinal Chemistry, 2006, vol. 41, # 9, p. 1084 - 1089]
[40]Current Patent Assignee: Weylchem (in: Internat. Chemicals Investors); INTERNATIONAL CHEMICALS INVESTORS SE - WO2008/12321, 2008, A1 Location in patent: Page/Page column 32-33
[41]Current Patent Assignee: Weylchem (in: Internat. Chemicals Investors); INTERNATIONAL CHEMICALS INVESTORS SE - WO2009/43761, 2009, A1 Location in patent: Page/Page column 11
[42]Shang, Ya-Jing; Qian, Yi-Ping; Liu, Xiao-Da; Dai, Fang; Shang, Xian-Ling; Jia, Wen-Qiang; Liu, Qiang; Fang, Jian-Guo; Zhou, Bo [Journal of Organic Chemistry, 2009, vol. 74, # 14, p. 5025 - 5031] Qian, Yi-Ping; Cai, Yu-Jun; Fan, Gui-Juan; Wei, Qing-Yi; Jie, Yang; Zheng, Li-Fang; Li, Xiu-Zhuang; Fang, Jian-Guo; Bo, Zhou [Journal of Medicinal Chemistry, 2009, vol. 52, # 7, p. 1963 - 1974]
[43]Current Patent Assignee: LAURUS LABS LIMITED - US2015/31921, 2015, A1 Location in patent: Paragraph 0090; 0091; 0092; 0093
[44]Current Patent Assignee: SHANDONG BOK BIOLOGICAL TECH - CN110577464, 2019, A Location in patent: Paragraph 0032; 0033
[45]Jungong, Christian S.; Novikov, Alexei V. [Synthetic Communications, 2012, vol. 42, # 24, p. 3589 - 3597,9]
[46]Current Patent Assignee: UNIVERSITY OF VIRGINIA - WO2021/236764, 2021, A1 Location in patent: Page/Page column 18; 67
[47]Current Patent Assignee: UNIVERSITY OF VIRGINIA - WO2021/236764, 2021, A1 Location in patent: Page/Page column 18; 67

5
[ 22255-22-7 ]
[ 63366-84-7 ]

Yield	Reaction Conditions	Operation in experiment
37%	With air In ethanol; water for 6h; Photolysis;
25%	In methanol for 7h; Photolysis;
	Irradiation; photocyclization;

Reference： [1]Rodríguez, Roi Álvarez; Lahoz, Inmaculada R.; Faza, Olalla Nieto; Cid, María Magdalena; Lopez, Carlos Silva [Organic and Biomolecular Chemistry, 2012, vol. 10, # 46, p. 9175 - 9182]
[2]Roberts; Pincock [Canadian Journal of Chemistry, 2003, vol. 81, # 6, p. 709 - 722]
[3]Letcher, R. M. [Organic Magnetic Resonance, 1981, vol. 16, # 3, p. 220 - 223]

6
[ 22255-22-7 ]
[ 83638-45-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogen
	With hydrogen In ethanol at 20℃; for 12h;

Reference： [1]Mannila, Erkki; Talvitie, Antti; Kolehmainen, Erkki [Phytochemistry, 1993, vol. 33, # 4, p. 813 - 816]
[2]Cardile, Venera; Lombardo, Laura; Spatafora, Carmela; Tringali, Corrado [Bioorganic Chemistry, 2005, vol. 33, # 1, p. 22 - 33]

7
[ 7311-34-4 ]
[ 1530-38-7 ]
[ 22255-22-7 ]
[ 94608-23-8 ]

Yield	Reaction Conditions	Operation in experiment
54%	Stage #1: ((4-methoxyphenyl)methyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.5h; Stage #2: 3,5-dimethoxybenzaldehdye In tetrahydrofuran; hexane at -78 - 20℃; for 19h;
1: 45% 2: 23%	With sodium hydride In tetrahydrofuran for 24h; Ambient temperature;
1: 3.56 g 2: 3.08 g	Stage #1: ((4-methoxyphenyl)methyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: 3,5-dimethoxybenzaldehdye In tetrahydrofuran

	With lithium hydroxide monohydrate In isopropyl alcohol at 60℃;
	Stage #1: ((4-methoxyphenyl)methyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at -78℃; for 2 - 4h; Stage #2: 3,5-dimethoxybenzaldehdye In tetrahydrofuran for 6.5 - 15.5h;	1 To a solution of 4-methoxy-benzylthphenylphosphonium bromide (12.5 g) in anhydrous tetrahydrofuran (200 ml_) at -78 0C was added n-butyllithium (2.44 M, 1.0 equiv), and the resulting red solution was stirred under argon for 2-4 h. A solution of 3,5-dimethoxybenzaldehyde (4.5 g) in tetrahydrofuran was added dropwise over 30 min and the mixture stirred for 6-15 h. The resulting cream suspension was poured into water and extracted with dichloromethane. The organic phase was washed with water, and removal of the solvent in vacuo afforded an oil. The oil was separated by flash column chromatography (49:1 hexane/ethyl acetate). The cis-stilbene eluted first as a clear oil followed by the trans isomer as a colorless solid or oil. Overall yield: 91 %. To a solution of the trans isomer (3.1.g) in anhydrous dichloromethane (150 mL) at -78 0C was added (dropwise) boron tribromide (1.0 M, 34.5 mL), and the resulting red solution was stirred under argon for 30 min. The solution was poured into water and extracted with dichloromethane. The organic phase was washed with water, and removal of the solvent in vacuo afforded an oil, which was separated by flash column chromatography (1 :1 hexane/ethyl acetate) to afford a colorless solid (2.26 g, 86%): mp 260 0C.

Reference： [1]Chang, Jang-Yang; Yang, Ming-Fang; Chang, Chi-Yen; Chen, Chi-Ming; Kuo, Ching-Chuan; Liou, Jing-Ping [Journal of Medicinal Chemistry, 2006, vol. 49, # 21, p. 6412 - 6415]
[2]Cushman, Mark; Nagatarathnam, Dhanapalan; Gopal, D.; He, Hu-Ming; Lin, Chii M.; Hamel, Ernest [Journal of Medicinal Chemistry, 1992, vol. 35, # 12, p. 2293 - 2306]
[3]Pettit, George R.; Grealish, Matthew P.; Jung, M. Katherine; Hamel, Ernest; Pettit, Robin K.; Chapuis, J.-Charles; Schmidt, Jean M. [Journal of Medicinal Chemistry, 2002, vol. 45, # 12, p. 2534 - 2542]
[4]Location in patent: scheme or table Gray, Erin E.; Rabenold, Lake E.; Goess, Brian C. [Tetrahedron Letters, 2011, vol. 52, # 46, p. 6177 - 6179]
[5]Current Patent Assignee: RESVERLOGIX CORP - WO2006/45010, 2006, A2 Location in patent: Page/Page column 155

8
[ 123-11-5 ]
[ 108957-75-1 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: diethyl 3,5-dimethoxybenzylphosphonate With sodium hydride In tetrahydrofuran-d8 at 0 - 20℃; for 0.166667h; Inert atmosphere; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at 28℃; for 3h; Inert atmosphere;
93%	With potassium <i>tert</i>-butylate In tetrahydrofuran for 1.25h; Reflux;	Trans 3,4',5-trimethoxystilbene (1) A round-bottomed flask (250 mL) equipped with magnetic stirring bar, reflux condenser and addition funnel was charged with anhydrous THF (500 mL) and KOtBu (6.53 g, 58 mmol, 1.2 equiv). After all the solids dissolved, the funnel was charged with a solution of 6 (14 g, 48 mmol, 1 equiv) and p-anisaldehyde (7.93 g, 58 mmol, 1.2 equiv) in THF (50 mL). The addition was made in a gentle stream over 15 min that generated an exotherm that brought the mixture near boiling. The mixture was then refluxed for 1 h after which time TLC showed the reaction was complete. The mixture was partitioned between H2O (100 mL) and EtOAc (200 mL). The organic layer was further washed with H2O (100 mL) followed by brine (100 mL). After drying the organic layer over anhydrous MgSO4, the solvent was rotary evaporated leaving crude 1 as a pale yellow solid (12.25 g, 93 %). Recrystallization from EtOH gave 1 as colorless plates. Mp 53-55 °C [lit.Takaoka and Spath 56-57 °C]. 1H NMR (CDCl3): δ 7.45 (d, J = 8.7 Hz, 2H), 7.05 (d, J = 16.4 Hz, 1H), 6.90 (d, J = 16.4 Hz, 1H), 6.89 (d, J = 8.7 Hz, 2H), 6.65 (d, J = 2.5 Hz, 2H), 6.38 (t, J = 2.2 Hz, 1H), 3.83 (s, 9H); 13C NMR (CDCl3): δ 161.26, 159.68, 139.97, 130.23, 129.01, 128.04, 126.86, 114.41, 104.63, 99.92, 55.59, 55.56. Elemental analysis calculated for C17H18O3: C, 75.53; H, 6.71. Found: C, 75.43; H, 6.63.
90.4%	In N,N-dimethyl-formamide

85%	With alumina*KF supported on silica In tetrahydrofuran at 100℃; for 0.0833333h; Microwave irradiation;
59%	With sodium methylate In N,N-dimethyl-formamide at 100℃; for 1.5h;
18.5%	Stage #1: diethyl 3,5-dimethoxybenzylphosphonate With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at 0 - 20℃; for 17h;
	Stage #1: diethyl 3,5-dimethoxybenzylphosphonate With sodium methylate In N,N-dimethyl-formamide Stage #2: 4-methoxy-benzaldehyde In N,N-dimethyl-formamide at 20 - 100℃; for 2h;
10.3 g	With sodium hydride In 1,2-dimethoxyethane; mineral oil at 20 - 85℃; Inert atmosphere;
	Stage #1: diethyl 3,5-dimethoxybenzylphosphonate With sodium methylate In N,N-dimethyl-formamide at 0℃; Stage #2: 4-methoxy-benzaldehyde In N,N-dimethyl-formamide at 100℃; for 5h;	4.1.7. Synthesis of (E)-1,3-dimethoxy-5-(4-methoxystyryl)benzene (16) 3,5-Dimethoxybenzyl bromide (14) was dissolved in excess triethyl phosphite and the solution was heated to 160 °C for 3 h. Excess triethyl phosphite was removed by heating at 80-90 °C under high vacuum and the remaining colorless phosphonate was used without further purification. A solution of the phosphonate (15) in DMF was treated with 5 equiv of NaOMe and cooled to 0 °C prior to the addition of the corresponding 4-methoxybenzaldehyde. After the reaction mixture was heated to 100 °C for 5 h and the reaction quenched with methanol/water, the precipitated crystals were filtered off and washed with water. Chromatography (silica gel, toluene) afforded the pure product. Compound 16: Yield: 94%, 1H NMR (CD3OD) δ 7.54 (2H, d, J = 8.7 Hz), 7.15 (1H, d, J = 16.2 Hz), 7.05 (1H, d, J = 15.7 Hz), 6.98 (2H, d, J = 8.7 Hz), 6.76 (2H, d, J = 2.4 Hz), 6.486 (1H, t), 3.91 (6H, s), 3.89 (3H, s). ES-MS: 271 [M+H]; HRMS calcd for C17H18O3 [M+H]+: 271.1300. Found: 271.1290.
	With sodium tert-pentoxide In tetrahydrofuran
	With sodium hydride In N,N-dimethyl-formamide at -10 - 0℃; for 7h;	Add all B and 400ml of DMF, add 68g of sodium hydride at -10 ° C, dropwise add 46g of anisaldehyde (dropwise for one hour), react at 0 ° C for 6 hours, pour into ice-water mixture, precipitate solid, filter, dry at 45 ° C, and obtain Product C.
1.61 g	With potassium hydroxide In tetrahydrofuran for 24h; Inert atmosphere;

Reference： [1]El-Deeb, Ibrahim Yussif; Funakoshi, Tatsuya; Shimomoto, Yuya; Matsubara, Ryosuke; Hayashi, Masahiko [Journal of Organic Chemistry, 2017, vol. 82, # 5, p. 2630 - 2640]
[2]Davis, Matthew C.; Groshens, Thomas J. [Tetrahedron Letters, 2012, vol. 53, # 27, p. 3521 - 3523]
[3]Malan, Elfranco; Swinny, Ewald; Ferreira, Daneel; Hall, Alida J. [Phytochemistry, 1988, vol. 27, # 7, p. 2309 - 2312]
[4]Location in patent: experimental part Dakdouki, Saada C.; Villemin, Didier; Bar, Nathalie [European Journal of Organic Chemistry, 2010, # 2, p. 333 - 337]
[5]Murias, Marek; Handler, Norbert; Erker, Thomas; Pleban, Karin; Ecker, Gerhard; Saiko, Philipp; Szekeres, Thomas; Jäger, Walter [Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 21, p. 5571 - 5578]
[6]Ao, Junli; Chen, Yuanmou; Xu, Xiaoling; Zhang, Xu; Yu, Yue; Yu, Peng; Hua, Erbing [Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 2092 - 2098]
[7]Privat, Christelle; Telo, Joao Paulo; Bernardes-Genisson, Vania; Vieira, Abel; Souchard, Jean-Pierre; Nepveu, Francoise [Journal of agricultural and food chemistry, 2002, vol. 50, # 5, p. 1213 - 1217]
[8]Location in patent: experimental part Smidrkal, Jan; Harmatha, Juraj; BudiSinsky, Milo; Vokae, Karel; ZIDEKc, Zdenik; Kmoniekova, Eva; Merkl, Roman; Filip, Vladimir [Collection of Czechoslovak Chemical Communications, 2010, vol. 75, # 2, p. 175 - 186]
[9]Location in patent: experimental part Das, Joydip; Pany, Satyabrata; Majhi, Anjoy [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 18, p. 5321 - 5333]
[10]Leláková, Veronika; Šmejkal, Karel; Jakubczyk, Karolina; Veselý, Ondřej; Landa, Přemysl; Václavík, Jiří; Bobáľ, Pavel; Pížová, Hana; Temml, Veronika; Steinacher, Theresa; Schuster, Daniela; Granica, Sebastian; Hanáková, Zuzana; Hošek, Jan [Food Chemistry, 2019, vol. 285, p. 431 - 440]
[11]Current Patent Assignee: SHANDONG BOK BIOLOGICAL TECH - CN110577464, 2019, A Location in patent: Paragraph 0031; 0033
[12]Jungong, Christian S.; Novikov, Alexei V. [Synthetic Communications, 2012, vol. 42, # 24, p. 3589 - 3597,9]

9
[ 501-36-0 ]
[ 77-78-1 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium hydroxide at 40℃; for 2h;
76%	With sodium hydroxide In water for 2h;
59%

Reference： [1]Huang, Xian-Feng; Ruan, Ban-Feng; Wang, Xiao-Ting; Xu, Chen; Ge, Hui-Ming; Zhu, Hai-Liang; Tan, Ren-Xiang [European Journal of Medicinal Chemistry, 2007, vol. 42, # 2, p. 263 - 267]
[2]Shi, Lei; Huang, Xian-Feng; Zhu, Zhen-Wei; Li, Huan-Qiu; Xue, Jia-Yu; Zhu, Hai-Liang; Liu, Chang-Hong [Australian Journal of Chemistry, 2008, vol. 61, # 6, p. 472 - 475]
[3]Mannila, Erkki; Talvitie, Antti; Kolehmainen, Erkki [Phytochemistry, 1993, vol. 33, # 4, p. 813 - 816]

10
[ 185249-89-2 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
61%	With toluene-4-sulfonic acid In benzene at 80℃; for 13h;
61%	With toluene-4-sulfonic acid In benzene for 13h; Heating;
	In dimethyl sulfoxide for 2h; Heating; Yield given;

With phosphoric acid In toluene for 5h; Reflux;

Reference： [1]Polunin, Konstantin E.; Polunina, Irina A.; Schmalz, Hans-Guenther [Mendeleev Communications, 2002, vol. 12, # 5, p. 178 - 179]
[2]Polunin; Schmalz; Polunina [Russian Chemical Bulletin, 2002, vol. 51, # 7, p. 1319 - 1324]
[3]Alonso, Emma; Ramon, Diego J.; Yus, Miguel [Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 417 - 421]
[4]Location in patent: experimental part Jian, Yujuan; Sun, Gaojun; Li, Jiaming; Su, Dan; Li, Chuanrun; Zhong, Guochen [Chinese Journal of Chemistry, 2011, vol. 29, # 7, p. 1423 - 1428]

11
[ 7311-34-4 ]
[ 1145-93-3 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium methylate at 20 - 100℃; for 2.5h;
60.7%	Stage #1: diethyl 4-methoxybenzylphosphonate With sodium methylate; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 3,5-dimethoxybenzaldehdye In N,N-dimethyl-formamide at 40℃; for 8h;
	With sodium methylate In N,N-dimethyl-formamide at 20℃; for 1h;

	Stage #1: diethyl 4-methoxybenzylphosphonate With 18-crown-6 ether; sodium methylate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 3,5-dimethoxybenzaldehdye In N,N-dimethyl-formamide at 20 - 120℃; for 6h;
	With sodium methylate In N,N-dimethyl-formamide at 0 - 100℃; for 26.5h; diastereoselective reaction;
	Stage #1: diethyl 4-methoxybenzylphosphonate With sodium hydride In tetrahydrofuran-d8 at 0 - 20℃; for 0.166667h; Inert atmosphere; Stage #2: 3,5-dimethoxybenzaldehdye In tetrahydrofuran at 28℃; for 3h; Inert atmosphere;

Reference： [1]Current Patent Assignee: SZEKERES - WO2005/16860, 2005, A2 Location in patent: Page/Page column 5
[2]Shen, Zhen Lu; Zhuo, Guang Lan; Jiang, Xuan Zhen [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 11, p. 2395 - 2398]
[3]Wang, Mingfu; Jin, Yi; Ho, Chi-Tang [Journal of Agricultural and Food Chemistry, 1999, vol. 47, # 10, p. 3974 - 3977]
[4]Heynekamp, Justin J.; Weber, Waylon M.; Hunsaker, Lucy A.; Gonzales, Amanda M.; Orlando, Robert A.; Deck, Lorraine M.; Vander Jagt, David L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 24, p. 7182 - 7189]
[5]Cardullo, Nunzio; Spatafora, Carmela; Musso, Nicolò; Barresi, Vincenza; Condorelli, Daniele; Tringali, Corrado [Journal of Natural Products, 2015, vol. 78, # 11, p. 2675 - 2683]
[6]El-Deeb, Ibrahim Yussif; Funakoshi, Tatsuya; Shimomoto, Yuya; Matsubara, Ryosuke; Hayashi, Masahiko [Journal of Organic Chemistry, 2017, vol. 82, # 5, p. 2630 - 2640]

12
[ 501-36-0 ]
[ 74-88-4 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h;
93%	Stage #1: (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol With potassium carbonate In acetone at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: methyl iodide In acetone at 25℃; for 12h; Inert atmosphere;
93%	Stage #1: (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol With potassium carbonate In acetone at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: methyl iodide In acetone at 25℃; for 12h; Inert atmosphere;	4 Permethylated Resveratrol (8) Paucifloral F was synthesized according to the scheme shown in Figure 3 (modification of the procedures described by Snyder et al . [5]) . Isopaucifloral F is synthesized according to the scheme shown in Figure 4 (modification of the procedures described by Snyder et al . [5] ) . Permethylated Resveratrol (8) Resveratrol (1.00 g, 4.38 mmol, 1.0 equiv) was dissolved in acetone (20 mL) and K2CO3 (5.45 g, 39.4 mmol, 9.0 equiv) was added in a single portion at 25 °C. After stirring the resultant slurry for 5 min at 25 °C, Mel (2.45 mL, 39.4 mmol, 9.0 equiv) was added slowly over the course of 5 min by syringe. The reaction mixture was stirred for 12 h at 25 °C. Upon completion, the reaction contents were quenched with saturated aqueous NH4C1 (25 mL) , poured into water (10 mL) , and extracted with EtOAc (3 χ 30 mL) . The combined organic extracts were then washed with water (30 mL) and brine (30 mL) , dried (MgS04) , filtered, and concentrated. The resultant crude, yellow oil was purified by flash column chromatography (silica gel, hexanes/EtOAc, 3:1) to afford permethylated resveratrol (8, 1.10 g, 93% yield) as a white solid.

88%	With sodium hydroxide at 40℃;
83%	With potassium carbonate In acetone for 8h; Heating;
76%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Cooling with ice; Inert atmosphere;	Preparation of (E)-1,3-Dimethoxy-5-(4-methoxystyryl)benzene (Compound 4b) To a solution of 1 (200 mg, 0.876 mmol) in DMF (2 mL) were added potassium carbonate (296 mg, 2.14 mmol) and iodomethane (0.402 mL, 6.43 mmol) under ice-cooling and nitrogen atmosphere. The resultant mixture was raised at ambient temperature and was allowed to be stirred for 24 h. Water was added to the reaction mixture under ice-cooling and stirred. The aqueous layer was extracted with ethyl acetate for three times. The combined organic layers were washed with water and brine, then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (7% ethyl acetate in n-hexane) to give the desired compound 4b (179 mg, 76%) as pale yellow solid. (1H-NMR (400MHz, CDCl3) δ 3.82 (9H, s), 6.37 (1H, t, J = 2.1 Hz), 6.65 (2H, d, J = 2.1 Hz), 6.89 (2H, d, J = 8.7 Hz), 6.89 (1H, d, J = 16.5 Hz), 7.04 (1H, d, J = 16.5 Hz), 7.44 (2H, d, J = 8.7 Hz); ESI-HRMS (positive ion): calcd for C17H18NaO3 ([M+Na]+) 293.1148 ; found 293.1143 HPLC Purity 92% (R.T. = 12.1 min, under gradient conditions as below).
68.6%	Stage #1: (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol With potassium carbonate In acetone for 0.5h; Stage #2: methyl iodide In acetone at 40℃; for 12h; Darkness;	5.1.2 Synthesis of permethylated resveratrol 7 To a solution of resveratrol (1.00g, 4.38mmol, 1.0 equiv) in dry acetone (25mL) was added K2CO3 (5.45g, 39.4mmol, 9.0 equiv). After stirring the reaction mixture for 30min, CH3I (2.45mL, 39.4mmol, 9.0 equiv) was added dropwise by syringe. Then the reaction mixture was stirred at 40°C in the dark for 12h. The reaction mixtures were monitored by TLC until completion. After being quenched with saturated aqueous NH4C1 (25mL), the reaction contents were poured into water (10mL), extracted with EtOAc (3×30mL). The combined organic extracts were then washed with water (30mL) and brine (30mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was further purified by column chromatography on silica gel (hexanes/EtOAc=8:1) to afford the permethylated Resveratrol 7 (white solid, 0.81g, 68.6%).
58%	With potassium carbonate In acetone for 24h;
46%	With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; for 5h; Inert atmosphere;
	With potassium carbonate In acetone

Reference： [1]Matsuda, Hisashi; Morikawa, Toshio; Toguchida, Iwao; Park, Ji-Young; Harima, Shoichi; Yoshikawa, Masayuki [Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 1, p. 41 - 50]
[2]Snyder, Scott A.; Thomas, Stephen B.; Mayer, Agathe C.; Breazzano, Steven P. [Angewandte Chemie - International Edition, 2012, vol. 51, # 17, p. 4080 - 4084]
[3]Current Patent Assignee: COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK - WO2013/49364, 2013, A1 Location in patent: Page/Page column 39; 42; 43
[4]Huang, Xian-Feng; Ruan, Ban-Feng; Wang, Xiao-Ting; Xu, Chen; Ge, Hui-Ming; Zhu, Hai-Liang; Tan, Ren-Xiang [European Journal of Medicinal Chemistry, 2007, vol. 42, # 2, p. 263 - 267]
[5]Rivera, Horacio; Shibayama, Mineko; Tsutsumi, Victor; Perez-Alvarez, Victor; Muriel, Pablo [Journal of Applied Toxicology, 2008, vol. 28, # 2, p. 147 - 155]
[6]Nakao, Syuhei; Mabuchi, Miyuki; Wang, Shenglan; Kogure, Yoko; Shimizu, Tadashi; Noguchi, Koichi; Tanaka, Akito; Dai, Yi [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 14, p. 3167 - 3172]
[7]Pan, Jialing; Xu, Tingting; Xu, Fengli; Zhang, Yali; Liu, Zhiguo; Chen, Wenbo; Fu, Weitao; Dai, Yuanrong; Zhao, Yunjie; Feng, Jianpeng; Liang, Guang [European Journal of Medicinal Chemistry, 2017, vol. 125, p. 478 - 491]
[8]Dobrydneva, Yuliya; Williams, Roy L; Morris, Gary Z; Blackmore, Peter F [Journal of cardiovascular pharmacology, 2002, vol. 40, # 3, p. 399 - 410]
[9]Rodríguez, Roi Álvarez; Lahoz, Inmaculada R.; Faza, Olalla Nieto; Cid, María Magdalena; Lopez, Carlos Silva [Organic and Biomolecular Chemistry, 2012, vol. 10, # 46, p. 9175 - 9182]
[10]Matsuda, Hisashi; Kageura, Tadashi; Morikawa, Toshio; Toguchida, Iwao; Harima, Shoichi; Yoshikawa, Masayuki [Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 4, p. 323 - 327]
[11]Kageura, Tadashi; Matsuda, Hisashi; Morikawa, Toshio; Toguchida, Iwao; Harima, Shoichi; Oda, Mamiko; Yoshikawa, Masayuki [Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 7, p. 1887 - 1893]
[12]Madadi, Nikhil R.; Zong, Hongliang; Ketkar, Amit; Zheng, Chen; Penthala, Narsimha R.; Janganati, Venumadhav; Bommagani, Shobanbabu; Eoff, Robert L.; Guzman, Monica L.; Crooks, Peter A. [MedChemComm, 2015, vol. 6, # 5, p. 788 - 794]

13
[ 123-11-5 ]
[ 397333-50-5 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: 4-methoxy-benzaldehyde; (3,5-dimethoxy-benzyl)phosphonic acid dimethyl ester With potassium hydroxide; 18-crown-6 ether In dichloromethane at 20℃; Stage #2: With iodine In n-heptane for 12h; Heating; Further stages.;

Reference： [1]Kim; Ko; Jae Eun Park; Jung; Sang Kwang Lee; Chun [Journal of Medicinal Chemistry, 2002, vol. 45, # 1, p. 160 - 164]

14
3,5,4'-trimethoxystilbene [ No CAS ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 2,2'-azobis(isobutyronitrile) In tetrahydrofuran for 8h; Reflux;
95%	With diphenyldisulfane In tetrahydrofuran for 2h; Reflux; Inert atmosphere;	(E)-3',4,5'-trimethoxy-stilbene (6): The mixture of (E/Z) isomers(200 mg, 0.745 mmol) and 30 mg (1.49 mmol) of (PhS)2 in 15.0 mL of anhydrous THF was refluxed under Ar for 2 h. Aftercooling, the solvent was evaporated under reduced pressure todryness, and the residue was purified by flash column chromatographyon silica gel, with hexane-EtOAc 8:2 to give pure 6 (190 mg,95%) as a colorless oil.
94%	With dichloro bis(acetonitrile) palladium(II) In dichloromethane at 20℃; for 12h;

75%	Stage #1: 3,5,4'-trimethoxystilbene With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 150℃; for 0.333333h; Inert atmosphere; Microwave irradiation; Stage #2: With t-butylnitrite In tetrahydrofuran for 1.5h; Inert atmosphere; stereoselective reaction;	14. Typical procedure: General procedure: To 1 equiv of substrate E/Z mixture in a microwave vial under a positive pressure of Ar was added 9-BBN (0.5 M in THF, 1.1 equiv). The vial was subjected to microwave irradiation (300 W, 20 min) and then cooled to room temperature. MNP dimer (0.6 equiv) dissolved in THF was added, and this solution was stirred for 90 min. The bright clue color of the MNP solution disappeared during this period, at which point the solvent was evaporated to yield the crude E stilbenoids. Purification was accomplished via column chromatography on silica gel.
0.65 g	With diphenyldisulfane In tetrahydrofuran for 4h; Inert atmosphere; Reflux;

Reference： [1]Location in patent: body text Alonso, Francisco; Riente, Paola; Yus, Miguel [Tetrahedron Letters, 2009, vol. 50, # 25, p. 3070 - 3073]
[2]Lara-Ochoa, Francisco; Sandoval-Minero, Leticia C.; Espinosa-Pérez, Georgina [Tetrahedron Letters, 2015, vol. 56, # 44, p. 5977 - 5979]
[3]Yu, Jinquan; Gaunt, Matthew J.; Spencer, Jonathan B. [Journal of Organic Chemistry, 2002, vol. 67, # 13, p. 4627 - 4629]
[4]Location in patent: experimental part Gray, Erin E.; Rabenold, Lake E.; Goess, Brian C. [Tetrahedron Letters, 2011, vol. 52, # 46, p. 6177 - 6179]
[5]Aldawsari, Fahad S.; Elshenawy, Osama H.; El Gendy, Mohamed A. M.; Aguayo-Ortiz, Rodrigo; Baksh, Shairaz; El-Kadi, Ayman O. S.; Velázquez-Martínez, Carlos A. [Journal of Enzyme Inhibition and Medicinal Chemistry, 2015, vol. 30, # 6, p. 884 - 895]

15
[ 7311-34-4 ]
[ 2746-25-0 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: p-Methoxybenzyl bromide With triethyl phosphate at 130℃; Stage #2: 3,5-dimethoxybenzaldehdye With sodium methylate In N,N-dimethyl-formamide at 20 - 100℃;

Reference： [1]Lu; Cai; Fang; Zhou; Liu; Wu, Longmin M. [Pharmazie, 2002, vol. 57, # 7, p. 474 - 478]

16
[ 94608-23-8 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With dichloro bis(acetonitrile) palladium(II) In dichloromethane at 20℃; for 14h;
60%	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 2h; Heating;

Reference： [1]Yu, Jinquan; Gaunt, Matthew J.; Spencer, Jonathan B. [Journal of Organic Chemistry, 2002, vol. 67, # 13, p. 4627 - 4629]
[2]Baag, Md. Merajuddin; Kar, Anirban; Argade, Narshinha P. [Tetrahedron, 2003, vol. 59, # 34, p. 6489 - 6492]

17
[ 22255-22-7 ]
[ 7311-34-4 ]
[ 123-11-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 73% 2: 60%	Stage #1: 3,5,4'-trimethoxy-trans-stilbene With ozone In methanol; dichloromethane at -78℃; Stage #2: With triphenylphosphine In methanol; dichloromethane for 0.5h;

Reference： [1]Fronza, Giovanni; Fuganti, Claudio; Serra, Stefano; Cisero, Marco; Koziet, Joseph [Journal of agricultural and food chemistry, 2002, vol. 50, # 10, p. 2748 - 2754]

18
[ 22255-22-7 ]
[ 42438-89-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With lithium thioethoxide In N,N-dimethyl-formamide at 160℃; for 2h;

Reference： [1]Polunin, Konstantin E.; Polunina, Irina A.; Schmalz, Hans-Guenther [Mendeleev Communications, 2002, vol. 12, # 5, p. 178 - 179]

19
[ 22255-22-7 ]
[ 42438-89-1 ]
[ 42438-89-1 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium thioethoxide In N,N-dimethyl-formamide at 160℃; for 2h; Title compound not separated from byproducts;

Reference： [1]Polunin; Schmalz; Polunina [Russian Chemical Bulletin, 2002, vol. 51, # 7, p. 1319 - 1324]

20
[ 7311-34-4 ]
[ 888071-72-5 ]
[ 22255-22-7 ]
[ 94608-23-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 79% 2: 2%	Stage #1: N'-[(1E)-(4-methoxyphenyl)methylene]-4-methylbenzenesulfonohydrazide With potassium <i>tert</i>-butylate In toluene at 0 - 20℃; for 1h; Stage #2: 3,5-dimethoxybenzaldehdye With 5,10,15,20-tetraphenyl porphyrinato iron hydroxide; Aliquat 336; phosphorous acid trimethyl ester In toluene at 40℃; for 48h;

Reference： [1]Aggarwal, Varinder K.; Fulton, J. Robin; Sheldon, Chris G.; De Vicente, Javier [Journal of the American Chemical Society, 2003, vol. 125, # 20, p. 6034 - 6035]

21
[ 25245-27-6 ]
4-methoxystyryltrimethylsilane [ No CAS ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium fluoride; tetrabutyl-ammonium chloride; potassium carbonate In water; N,N-dimethyl-formamide; toluene at 70℃;

Reference： [1]Jeffery, Tuyet; Ferber, Benoît [Tetrahedron Letters, 2003, vol. 44, # 1, p. 193 - 197]

22
[ 134029-62-2 ]
[ 22255-22-7 ]
[ 78916-50-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: (E)-3,4,4',5-tetramethoxystilbene With sodium In tetrahydrofuran at 20℃; for 6h; Stage #2: With water In tetrahydrofuran at 0℃;

Reference： [1]Azzena, Ugo; Dettori, Giovanna; Idini, Maria Vittoria; Pisano, Luisa; Sechi, Grazia [Tetrahedron, 2003, vol. 59, # 40, p. 7961 - 7966]

23
[ 134029-62-2 ]
[ 22255-22-7 ]
[ 83638-45-3 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: (E)-3,4,4',5-tetramethoxystilbene With sodium In tetrahydrofuran at 0℃; for 2h; Stage #2: With water In tetrahydrofuran at 0℃;

Reference： [1]Azzena, Ugo; Dettori, Giovanna; Idini, Maria Vittoria; Pisano, Luisa; Sechi, Grazia [Tetrahedron, 2003, vol. 59, # 40, p. 7961 - 7966]

24
[ 123-11-5 ]
[ 71135-82-5 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-methoxy-benzaldehyde; (3,5-Dimethoxy-benzylidene)-triphenyl-λ⁵-phosphane With lithium diisopropyl amide In tetrahydrofuran at 0 - 20℃; Stage #2: With iodine In n-heptane for 12h; Heating;

Reference： [1]Lee, Hyun Jung; Seo, Jai Woong; Lee, Bong Ho; Chung, Kyoo-Hyun; Chi, Dae Yoon [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 2, p. 463 - 466]

25
[ 123-11-5 ]
[ 667458-79-9 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 3,5-dimethoxybenzyl 3,5-bis(trifluoromethyl)phenyl sulfone With N,N,N,N,N,N-hexamethylphosphoric triamide; iminotris(dimethylamino)phosphorane In tetrahydrofuran for 0.5h; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at 20℃; for 16h;
74%	With N,N,N,N,N,N-hexamethylphosphoric triamide; P₄-t-Bu In tetrahydrofuran at -78℃; for 48h;

Reference： [1]Alonso, Diego A.; Fuensanta, Monica; Najera, Carmen; Varea, Montserrat [Journal of Organic Chemistry, 2005, vol. 70, # 16, p. 6404 - 6416]
[2]Alonso, Diego A.; Nájera, Carmen; Varea, Montserrat [Tetrahedron Letters, 2004, vol. 45, # 3, p. 573 - 577]

26
[ 637-69-4 ]
[ 25245-27-6 ]
[ 22255-22-7 ]
1,3-dimethoxy-5-(1-(4-methoxyphenyl)vinyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With palladium; triethylamine at 100℃; for 24h; Overall yield = 94 %;	4.2. Procedure for the Heck coupling reactions The reaction mixture, consisting of 79.2 mg (0.3 mmol) of 1-iodo-3,5-dimethoxybenzene (2), 67.1 mg (0.5 mmol) of 1-methoxy-4-vinylbenzene (3) and a 219.6 mg of triethylamine, was prepared in a 5 mL vial, and then transferred to a 20 mL Schlenk flask containing 1 g of the solid catalyst, where the reaction mixture got completely adsorbed. The whole system was then heated to 100 °C for 24 h. After this time, the reaction was cooled until 65 °C and then washed with hexane (first 210 mL and then 25 mL). Finally, the residual solvent on the solid catalyst was removed at reduced pressure. The resulting solid was then ready for further reuse. The hexane extract was analysed by gas chromatography and, after solvent removal, by NMR. The (E)-1,3-dimethoxy-5-(4-methoxystyryl)benzene (4) product was purified by medium pressure column chromatography (Combiflash) using a silica gel column and a mixture hexane/ethylacetate 99:1 as eluent until the desired product appeared in the collected fractions, and then changing to pure ethyl acetate as eluent. The desired product was isolated (69.3 mg, 86%) as a white solid and characterised by NMR;36 [Found C 75.28 H 6.64 requires C,75.53, H, 6.71]; GC conditions: Agilent J&W CG Column HP-5 30 m25 mm0.25 mm, helium as carrier gas, 230 °C injector T, 250 °C detector T, 20 psi head column pressure, 2 mL min-1 flux, oven temperature program 70 °C (1 min), 20 °C min-1, 250 °C (7.5 min), retention time 11.3 min; δH (400 MHz, CDCl3) 7.35 (d, 2H, J=8.7 Hz), 6.95 (d, 1H, J=16.2 Hz), 6.83-6.80 (m, 3H), 6.57 (d, 2H, J=1.9 Hz), 6.29 (t, 1H, J=1.8 Hz), 3.73 (s, 9H); δC (100.6 MHz, CDCl3, APT) 161.0 (C), 159.4 (C), 139.7 (C), 130.0 (C), 128.8 (CH), 127.8 (CH), 126.6 (CH), 114.2 (CH), 99.7 (CH), 55.3 (CH3); m/z (EI) 270 (M+).
	With N-Methyldicyclohexylamine; tetrabutylammomium bromide In N,N-dimethyl acetamide; water at 120℃; for 13h;

Reference： [1]Martínez, Alejandro V.; García, José I.; Mayoral, José A. [Tetrahedron, 2017, vol. 73, # 38, p. 5581 - 5584]
[2]Botella, Luis; Nájera, Carmen [Tetrahedron, 2004, vol. 60, # 26, p. 5563 - 5570]

27
[ 153139-20-9 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With toluene-4-sulfonic acid In toluene for 2.5h; Heating / reflux;	11 Example 11; Synthesis of (E)-trimethylresveratrol:; 2 g of l-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanol prepared according to Example 7 or Example 8 (6.9 mmol) and 0.019 g of p-tolunesulphonic acid (PTSA) monohydrate (6 mol%) are introduced into 200 ml of toluene in a 250 ml three-necked round-bottomed flask. The mixture is brought to reflux for 2 h 30 while removing the water by azeotropic distillation. The mixture is brought back to ambient temperature, 30 ml of a saturated sodium bicarbonate solution are added, washing is carried out with 30 ml of water and the toluene phase is concentrated to produce 1.95 g of a yellow oil. This oil is taken up in 3.8 ml of methanol and the mixture is brought to reflux and allowed to return to ambient temperature. The precipitate obtained is filtered off and washed on the filter with 1 ml of methanol. 1.31 g of light brown precipitate are recovered, which precipitate has a melting point of 55-56°C and corresponds, by NMR, to (E)- trimethylresveratrol, i.e. a yield of 70%.NMR (CDCl3) 200 MHzProton: δ 3.83 s (9H); δ 6.40 1 (IH); δ 6.68 d (2H); δ 6.9 d (IH); δ 6.92 d (2H); δ7.10 d (IH); δ 7.48 d (2H) C13: δ 55.32; 55.37 (OCH3); δ 99.73; 104.49; 114.27; (arom. CH); 126.68;128.84 (ethylen. CH); δ 127.97; 130.04; 139.84; 159.54; 161.13 (arom.CH).
34%	With toluene-4-sulfonic acid In benzene for 6h; Heating;

Reference： [1]Current Patent Assignee: Weylchem (in: Internat. Chemicals Investors); INTERNATIONAL CHEMICALS INVESTORS SE - WO2008/12321, 2008, A1 Location in patent: Page/Page column 25
[2]Roberts; Pincock [Canadian Journal of Chemistry, 2003, vol. 81, # 6, p. 709 - 722]

28
[ 637-69-4 ]
[ 40243-87-6 ]
1,2-bis(4-methoxyphenyl)ethene [ No CAS ]
[ 22255-22-7 ]
(E)-3,3',5,5'-tetramethoxystilbene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	In dichloromethane at 40℃; for 1.5h;
1: 63 % Chromat. 2: 19 % Chromat. 3: 18 % Chromat.	In toluene for 1h; Heating;

Reference： [1]Velder, Janna; Ritter, Stefanie; Lex, Johann; Schmalz, Hans-Guenther [Synthesis, 2006, # 2, p. 273 - 278]
[2]Ferre-Filmon, Karine; Delaude, Lionel; Demonceau, Albert; Noels, Alfred F. [European Journal of Organic Chemistry, 2005, # 15, p. 3319 - 3325]

29
[ 637-69-4 ]
[ 20469-65-2 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With tri-tert-butyl phosphine; caesium carbonate; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In 1,4-dioxane at 120℃; Inert atmosphere;
14%	With sodium acetate In N,N-dimethyl-formamide at 140 - 150℃; for 48h;
	With tetrabutylammomium bromide; triethylamine In N,N-dimethyl acetamide at 120℃; for 12h;

Reference： [1]Location in patent: experimental part Iijima, Takashi; Makabe, Hidefumi [Bioscience, Biotechnology and Biochemistry, 2009, vol. 73, # 11, p. 2547 - 2548]
[2]Eisnor, Charles R.; Gossage, Robert A.; Yadav, Paras N. [Tetrahedron, 2006, vol. 62, # 14, p. 3395 - 3401]
[3]Brown, Jonathan W.; Jarenwattananon, Nanette N.; Otto, Trenton; Wang, James L.; Glöggler, Stefan; Bouchard, Louis-S. [Catalysis Communications, 2015, vol. 65, p. 105 - 107]

30
[ 637-69-4 ]
[ 40243-87-6 ]
1,2-bis(4-methoxyphenyl)ethene [ No CAS ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 40℃; for 1.5h; Title compound not separated from byproducts;

Reference： [1]Velder, Janna; Ritter, Stefanie; Lex, Johann; Schmalz, Hans-Guenther [Synthesis, 2006, # 2, p. 273 - 278]

31
[ 24131-30-4 ]
[ 123-11-5 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: (3,5-dimethoxybenzyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at 20℃;
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / Inert atmosphere; Cooling with acetone-dry ice 1.2: 20 °C / Inert atmosphere 2.1: diphenyldisulfane / tetrahydrofuran / 4 h / Inert atmosphere; Reflux

Reference： [1]Roberti, Marinella; Pizzirani, Daniela; Recanatini, Maurizio; Simoni, Daniele; Grimaudo, Stefania; Di Cristina, Antonietta; Abbadessa, Vincenzo; Gebbia, Nicola; Tolomeo, Manlio [Journal of Medicinal Chemistry, 2006, vol. 49, # 10, p. 3012 - 3018]
[2]Aldawsari, Fahad S.; Elshenawy, Osama H.; El Gendy, Mohamed A. M.; Aguayo-Ortiz, Rodrigo; Baksh, Shairaz; El-Kadi, Ayman O. S.; Velázquez-Martínez, Carlos A. [Journal of Enzyme Inhibition and Medicinal Chemistry, 2015, vol. 30, # 6, p. 884 - 895]

32
[ 24131-30-4 ]
[ 123-11-5 ]
[ 22255-22-7 ]
[ 94608-23-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 35% 2: 9%	Stage #1: (3,5-dimethoxybenzyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran; hexane at 20℃; for 12h; Further stages.;
	With sodium hydride In tetrahydrofuran
42.857 % de	With sodium hydride In tetrahydrofuran at 0 - 20℃; for 14h; Overall yield = 83 %;

Reference： [1]Mizuno, Cassia S.; Ma, Guoyi; Khan, Shabana; Patny, Akshay; Avery, Mitchell A.; Rimando, Agnes M. [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 7, p. 3800 - 3808]
[2]Simoni, Daniele; Roberti, Marinella; Invidiata, Francesco Paolo; Aiello, Enrico; Aiello, Stefania; Marchetti, Paolo; Baruchello, Riccardo; Eleopra, Marco; Di Cristina, Antonietta; Grimaudo, Stefania; Gebbia, Nicola; Crosta, Lucia; Dieli, Francesco; Tolomeo, Manlio [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 12, p. 3245 - 3248]
[3]Moodie, Lindon W. K.; Trepos, Rozenn; Cervin, Gunnar; Brathen, Kari Anne; Lindgard, Bente; Reiersen, Rigmor; Cahill, Patrick; Pavia, Henrik; Hellio, Claire; Svenson, Johan [Journal of Natural Products, 2017, vol. 80, # 7, p. 2001 - 2011]

33
[ 501-36-0 ]
[ 77-78-1 ]
[ 22255-22-7 ]
[ 58436-29-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 89% 2: 8%	With potassium carbonate In acetone for 24h; Heating;

Reference： [1]Cardile, Venera; Lombardo, Laura; Spatafora, Carmela; Tringali, Corrado [Bioorganic Chemistry, 2005, vol. 33, # 1, p. 22 - 33]

34
[ 537-42-8 ]
[ 74-88-4 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
		Example 20: Synthesis of (E) -1 , 3-dimethoxy-5- (4-methoxy- styryl) benzene ARS8.; To a solution of <strong>[537-42-8]pterostilbene</strong> (lOOmg, 0.39mM) in DMF was added potassium carbonate (108mg, 0.78mM) . The reaction stirred for 30 min and methyl iodide was added (37muL,0.58mM) . The mixture was stirred for 12h at room temperature and poured into water. The mixture was extracted with ethyl acetate and the crude purified using flash chromatography eluting with ethyl acetate/hexanes (4:1) . <n="29"/>ARS8: (E) -1, 3-dimethoxy-5- (4-methoxystyryl) benzene . White solid. 1H NMR (CDCl3, 400MHz): delta 3.83 (s, 9H); 6.39 (s, IH); 6.67 (s, 2H); 6.89 (s, 2H); 6.92 (d, IH, J= 8); 7.02 (d, IH, J=8); 7.45 (d, 2H, J= 8). 13C NMR (CDCl3, 400MHz): delta 55.3 (3C), 99.6, 104.3 (2C), 114.1 (2C), 126.5, 127.8 (2C), 128.7, 129.9, 139.7, 159.4, 161.0 (2C). HRMS: CaIc for C34H36NaO6563.24096, found 563.24419 (2M+Na) .

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5767 - 5772
[2]Patent: WO2008/70872,2008,A1 .Location in patent: Page/Page column 26-27

35
[ 1003857-12-2 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium <i>tert</i>-butylate In toluene for 3h; Heating / reflux;	16; 17 Example 16; Synthesis of (E)-trimethylresveratrol:; 50 g ofN-[l-(3 ,5 -dimethoxyphenyl)-2-(4-methoxyphenyl)ethylidene] -N ' - tosylhydrazine prepared according to Example 13 (0.110 mol) and 27.16 g of potassium tert-butoxide (0.242 mol) in 1 1 of toluene comprising 2.5 g of Triton X100 are introduced into a 2 1 three-necked round-bottomed flask. The mixture is brought to reflux for 3 h, cooling is carried out to ambient temperature, 1 1 of water is added, separation by settling is carried out and the organic phase is recovered. The aqueous phase is re-extracted with 0.4 litre of toluene. The combined organic phases are concentrated on a rotary evaporator to result in 29.6 g of crude product in the form of a yellow solid. This product is taken up in 90 ml of ethanol at ambient temperature overnight with stirring to result in 17.4 g of 3,5,4'-trimethylresveratrol in the form of a slightly orangey solid. The product is recrystallized on 34 ml of methanol and filtered at 0-50C to result in 16.6 g of (E)-trimethylresveratrol in the form of a white solid, i.e. a yield of 58% with respect to the starting hydrazone, which exhibits a melting point at 56-57°C.NMR (CDCl3) 200 MHzProton: δ 3.83 s (9H); δ 6.40 1 (IH); δ 6.68 d (2H); δ 6.9 d (IH); δ 6.92 d (2H); δ7.10 d (IH); δ 7.48 d (2H) C13: δ 55.32; 55.37 (OCH3); δ 99.73; 104.49; 114.27 (arom. CH); 126.68; 128.84 (ethylen. CH); δ 127.97; 130.04; 139.84; 159.54; 161.13 (arom. CH).; Example 17; Synthesis of (E)-trimethylresveratrol:; The same reaction as in Example 16 is carried out on 2.5 g of N-[l-(3,5- dimethoxyphenyl)-2-(4-methoxyphenyl)ethylidene]-N'-tosylhydrazine in 12.5 ml of toluene in the presence of 1.36 g of potassium tert-butoxide and of 0.125 g of Triton X100 to result in 1.47 g of crude 3,5,4'-trimethylresveratrol, which is recrystallized from 5 ml of methanol to result in 0.91 g of (E)-trimethylresveratrol in the form of a white solid, i.e. a yield of 63.6% with respect to the starting hydrazone.

Reference： [1]Current Patent Assignee: Weylchem (in: Internat. Chemicals Investors); INTERNATIONAL CHEMICALS INVESTORS SE - WO2008/12321, 2008, A1 Location in patent: Page/Page column 28-29

36
[ 22255-22-7 ]
[ 33513-42-7 ]
[ 906457-43-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With trichlorophosphate at 20℃; for 1h; Cooling with ice;	1.1 Step 1: A 100 mL round bottom flask was charged with N, N-dimethylformamide (30 mL) under an ice-water bath, In addition, resveratrol (13.5 g, 0.075 mol) was weighed, dissolved in 10 mL of N, N-dimethylformamide, Then it was added to a round bottom flask, and then phosphorus oxychloride (7 mL, 0.075 mol) was slowly added dropwise, After the addition was completed and returned to room temperature reaction, the reaction was stirred 1h; after the reaction was taken a 1000mL beaker, Add 500mL of ice water and 100mL of ethyl acetate, and then the reaction solution was added dropwise thereto, Stirred by adding sodium carbonate solids in portions until there was no bubble generation, pale yellow solid precipitated overnight, suction filtered, dried, Column chromatography (eluent dichloromethane: petroleum ether = 1: 2, v / v) afforded intermediate B- (E)-2,4-dimethoxy-6-(4-methoxystyrene)benzaldehyde as a pale yellow solid powder in 93% yield,
92.7%	With trichlorophosphate In N,N-dimethyl-formamide at 20℃; for 1h; Cooling with ice;	1.1 taking the 100 ml round-bottom flask, add in the ice water bath under N, N - dimethyl formamide (30 ml), in addition said takes the white black false hellebore to be mellow three methyl ether (13.5g, 0 . 075 µM), for 10 ml N, N - dimethyl formamide dissolved, then its entry into the round-bottom flask, then slowly dropping phosphorus oxychloride (7 ml, 0 . 075 µM), after dropping the restoration to room temperature reaction, stirring reaction 1h. After the reaction is finished taking a 1000 ml beaker, add 500 ml ice water and 100 ml ethyl acetate, then added to the reaction fluid by drop wherein several times under stirring adding sodium carbonate solid until the bubble generating, overnight precipitated yellow solid, filtering, drying, column chromatography (E)- 2, 4 - dimethoxy -6 - (4 - methoxybenzene ethylene) benzaldehyde (compound A). The product is a yellow solid, yield 92.7%,
69%	With trichlorophosphate at 20℃; for 0.5h;

69%	Stage #1: 3,5,4'-trimethoxy-trans-stilbene; N,N-dimethyl-formamide With trichlorophosphate at 20℃; for 0.5h; Stage #2: With water Further stages.;
60.4%	With trichlorophosphate at 20℃; for 1h; Cooling with ice;	5.1.3 Synthesis of (E)-2, 4-dimethoxy-6-(4-methoxystyryl)benzaldehyde 8 To a solution of 0.54g compound 7 (2mmol, 1.0 equiv) in dry DMF (10mL) was added dropwise POCl3 (0.4mL, 4.2mmol, 2.1 equiv) slowly while cooling in an ice-water bath. After stirring at room temperature for 1h, the solution was added to ice-water and kept stirring 30min, the solid precipitated, filtered. The residue was purified by column chromatography on silica gel (hexanes/EtOAc/CH2Cl2=8:1:1) to generate 8 (yellow solid, 0.36g, 60.4%).
	With trichlorophosphate at 0 - 20℃; for 0.75h;
	With trichlorophosphate at 0℃;
	With trichlorophosphate at 20℃; for 1h; Cooling with ice;	1 a, first add resveratrol dimethyl ether (B1) to N, N-dimethylformamide, then slowly add phosphorus oxychloride, resveratrol dimethyl ether and phosphorus oxychloride in an ice bath The molar ratio is 1:1. After the completion of the dropwise addition, the reaction is returned to room temperature. After 1 hour, the reaction is stopped, and then the reaction solution is added dropwise to a mixed solution of ice water and ethyl acetate. The volume of ice water and ethyl acetateThe ratio is 5:1, and the sodium carbonate solid is added in portions until no bubbles are formed.After stirring overnight, a pale yellow solid formed, which was filtered and dried.Finally column chromatography (dichloromethane: petroleum ether = 1:2, v / v), (E)-2,4-dimethoxy-6-(4-methoxystyrene) benzaldehyde ( C1).
	With trichlorophosphate In acetonitrile at 0 - 20℃; for 15h;
	With trichlorophosphate In acetonitrile at 0 - 20℃; for 1h;	1 Take a 100ml round bottom flask, Add the red sandalwood derivative (2mmol, 568mg), Add 10mL acetonitrile to dissolve, DMF (2 mmol, 153 uL) was slowly added dropwise at room temperature; The ice water was cooled to about 0 ° C and POCl 3 (13 mmol, 1.2 mL) was slowly added dropwise; After the dropwise addition, the round bottom flask was rotated to room temperature to stir the reaction. After 1 h, the reaction solution was poured into ice water and quenched, and the pH was adjusted to neutral with NaOH solution; Stir for 1h, The filter was allowed to stand for filtration and dried to give a bright yellow solid. The crude product was separated by column chromatography (200-300 mesh silica gel) using dichloromethane: petroleum ether = 3:1 as eluent. Concentrated to give a pale yellow solid with a purity greater than 99% (E)-2,4-Dimethoxy-6-(4-ethoxystyrene)benzaldehyde.
	Stage #1: 3,5,4'-trimethoxy-trans-stilbene; N,N-dimethyl-formamide With trichlorophosphate In acetonitrile at 20℃; for 1h; Stage #2: With sodium hydroxide In water; acetonitrile	1 Weigh B (811mg, 3mmol) and dissolve it in a 100mL round bottom flask with acetonitrile.Add N, N-dimethylformamide (DMF, 458 μL), then slowly dropwise add phosphorus oxychloride(280 μL, 3 mmol); returned to room temperature after the dropwise addition, and stirred for 1 h,Stop when the reaction is complete. Take a 1000mL beaker and add 500mL ice water.Then the reaction solution was added dropwise thereto, and sodium hydroxide solution was added to make it neutral under stirring.After stirring overnight, a pale yellow solid precipitated, filtered with suction, dried, and separated by column chromatography.(Dichloromethane: petroleum ether = 3: 1) gave C as a yellow solid.

Reference： [1]Current Patent Assignee: HEFEI UNIVERSITY OF TECHNOLOGY - CN107417532, 2017, A Location in patent: Paragraph 0015; 0034; 0035
[2]Current Patent Assignee: HEFEI UNIVERSITY OF TECHNOLOGY - CN104892556, 2017, B Location in patent: Paragraph 0032
[3]Huang, Xian-Feng; Ruan, Ban-Feng; Wang, Xiao-Ting; Xu, Chen; Ge, Hui-Ming; Zhu, Hai-Liang; Tan, Ren-Xiang [European Journal of Medicinal Chemistry, 2007, vol. 42, # 2, p. 263 - 267]
[4]Shi, Lei; Huang, Xian-Feng; Zhu, Zhen-Wei; Li, Huan-Qiu; Xue, Jia-Yu; Zhu, Hai-Liang; Liu, Chang-Hong [Australian Journal of Chemistry, 2008, vol. 61, # 6, p. 472 - 475]
[5]Pan, Jialing; Xu, Tingting; Xu, Fengli; Zhang, Yali; Liu, Zhiguo; Chen, Wenbo; Fu, Weitao; Dai, Yuanrong; Zhao, Yunjie; Feng, Jianpeng; Liang, Guang [European Journal of Medicinal Chemistry, 2017, vol. 125, p. 478 - 491]
[6]Greer, Aleksandra K.; Madadi, Nikhil R.; Bratton, Stacie M.; Eddy, Sarah D.; Mazerska, Zofia; Hendrickson, Howard P.; Crooks, Peter A.; Radominska-Pandya, Anna [Chemical Research in Toxicology, 2014, vol. 27, # 4, p. 536 - 545]
[7]Madadi, Nikhil R.; Zong, Hongliang; Ketkar, Amit; Zheng, Chen; Penthala, Narsimha R.; Janganati, Venumadhav; Bommagani, Shobanbabu; Eoff, Robert L.; Guzman, Monica L.; Crooks, Peter A. [MedChemComm, 2015, vol. 6, # 5, p. 788 - 794]
[8]Current Patent Assignee: HEFEI UNIVERSITY OF TECHNOLOGY - CN108558813, 2018, A Location in patent: Paragraph 0054; 0056; 0116; 0118
[9]Chen, Liu Zeng; Yao, Li; Jiao, Ming Ming; Shi, Jing Bo; Tan, Yue; Ruan, Ban Feng; Liu, Xin Hua [European Journal of Medicinal Chemistry, 2019, vol. 175, p. 114 - 128]
[10]Current Patent Assignee: HEFEI UNIVERSITY OF TECHNOLOGY - CN110105316, 2019, A Location in patent: Paragraph 0034; 0037
[11]Current Patent Assignee: HEFEI UNIVERSITY OF TECHNOLOGY - CN110041204, 2019, A Location in patent: Paragraph 0024; 0028

37
[ 2746-25-0 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 140 °C 2.1: sodium methoxide; 18/6 crown ether / dimethylformamide / 0.08 h / 20 °C 2.2: dimethylformamide / 6 h / 20 - 120 °C

Reference： [1]Heynekamp, Justin J.; Weber, Waylon M.; Hunsaker, Lucy A.; Gonzales, Amanda M.; Orlando, Robert A.; Deck, Lorraine M.; Vander Jagt, David L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 24, p. 7182 - 7189]

38
[ 877-88-3 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 90 percent / toluene / 14 h / Heating 2.1: n-BuLi / tetrahydrofuran / 3 h / -78 °C 2.2: tetrahydrofuran / 5 h / 20 °C 3.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 4.1: 92 percent / potassium carbonate / acetone / 5 h / Heating
	Multi-step reaction with 2 steps 1: tetrabutylammonium iodide / 110 - 130 °C 2: 1.7 g / sodium hydride / dimethylformamide / 20 °C
	Multi-step reaction with 3 steps 1.1: NaH / acetonitrile / 24 h / 20 °C 2.1: MnSO₄*H₂O; H₂O₂; NaHCO₃ buffer / acetonitrile / 20 °C 3.1: phosphazene (triaminoiminophosphorane) base; HMPA / tetrahydrofuran / 0.5 h 3.2: 74 percent / tetrahydrofuran / 16 h / 20 °C

	Multi-step reaction with 2 steps 1.1: tetrahydrofuran / Heating 2.1: LDA / tetrahydrofuran / 0 - 20 °C 2.2: I₂ / heptane / 12 h / Heating
	Multi-step reaction with 2 steps 1.1: 130 °C 2.1: sodium methoxide / dimethylformamide 2.2: dimethylformamide / 2 h / 20 - 100 °C
	Multi-step reaction with 2 steps 1.1: 93 percent / 8 h / 180 °C 2.1: KOH; 18-crown-6 / CH₂Cl₂ / 20 °C 2.2: 94 percent / I₂ / heptane / 12 h / Heating
	Multi-step reaction with 2 steps 2: 90.4 percent / dimethylformamide
	Multi-step reaction with 2 steps 1.1: 3 h / 160 °C 2.1: sodium methylate / N,N-dimethyl-formamide / 0 °C 2.2: 5 h / 100 °C
	Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C 3.1: 1,2-dibromo-1,1,2,2-tetrachloroethane; alumina-supported potassium hydroxide / tetrahydrofuran; <i>tert</i>-butyl alcohol / 8 h / 20 °C
	Multi-step reaction with 2 steps 1.1: 7 h / 135 °C 2.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C 2.2: 17 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1.1: water / 12 h / 80 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran-d8 / 0.17 h / 0 - 20 °C / Inert atmosphere 2.2: 3 h / 28 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: hexamethylenetetramine / water / 12 h / 120 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran-d8 / 0.17 h / 0 - 20 °C / Inert atmosphere 2.2: 3 h / 28 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: tetrabutylammomium bromide / 160 °C 2: sodium hydride / N,N-dimethyl-formamide / 7 h / -10 - 0 °C

Reference： [1]Gao, Mingzhang; Wang, Min; Miller, Kathy D.; Sledge, George W.; Hutchins, Gary D.; Zheng, Qi-Huang [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5767 - 5772]
[2]Li, Yue-Qing; Li, Ze-Lin; Zhao, Wei-Jie; Wen, Rui-Xing; Meng, Qing-Wei; Zeng, Yi [European Journal of Medicinal Chemistry, 2006, vol. 41, # 9, p. 1084 - 1089]
[3]Alonso, Diego A.; Fuensanta, Monica; Najera, Carmen; Varea, Montserrat [Journal of Organic Chemistry, 2005, vol. 70, # 16, p. 6404 - 6416]
[4]Lee, Hyun Jung; Seo, Jai Woong; Lee, Bong Ho; Chung, Kyoo-Hyun; Chi, Dae Yoon [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 2, p. 463 - 466]
[5]Privat, Christelle; Telo, Joao Paulo; Bernardes-Genisson, Vania; Vieira, Abel; Souchard, Jean-Pierre; Nepveu, Francoise [Journal of agricultural and food chemistry, 2002, vol. 50, # 5, p. 1213 - 1217]
[6]Kim; Ko; Jae Eun Park; Jung; Sang Kwang Lee; Chun [Journal of Medicinal Chemistry, 2002, vol. 45, # 1, p. 160 - 164]
[7]Malan, Elfranco; Swinny, Ewald; Ferreira, Daneel; Hall, Alida J. [Phytochemistry, 1988, vol. 27, # 7, p. 2309 - 2312]
[8]Das, Joydip; Pany, Satyabrata; Majhi, Anjoy [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 18, p. 5321 - 5333]
[9]Soiderman, Stefan C.; Schwan, Adrian L. [Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10978 - 10984]
[10]Ao, Junli; Chen, Yuanmou; Xu, Xiaoling; Zhang, Xu; Yu, Yue; Yu, Peng; Hua, Erbing [Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 2092 - 2098]
[11]El-Deeb, Ibrahim Yussif; Funakoshi, Tatsuya; Shimomoto, Yuya; Matsubara, Ryosuke; Hayashi, Masahiko [Journal of Organic Chemistry, 2017, vol. 82, # 5, p. 2630 - 2640]
[12]El-Deeb, Ibrahim Yussif; Funakoshi, Tatsuya; Shimomoto, Yuya; Matsubara, Ryosuke; Hayashi, Masahiko [Journal of Organic Chemistry, 2017, vol. 82, # 5, p. 2630 - 2640]
[13]Current Patent Assignee: SHANDONG BOK BIOLOGICAL TECH - CN110577464, 2019, A

39
[ 10272-07-8 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: HNO₂ 1.2: 33 percent / CuBr 2.1: Mg; iodine / tetrahydrofuran / 0.5 h / Heating 2.2: 96 percent / tetrahydrofuran / 0.5 h / Heating 3.1: 34 percent / p-toluenesulfonic acid / benzene / 6 h / Heating
	Multi-step reaction with 2 steps 1: KF; n-Bu₄NCl; K₂CO₃ / bis(dibenzylideneacetone)palladium / toluene; dimethylformamide; H₂O / 70 °C

Reference： [1]Roberts; Pincock [Canadian Journal of Chemistry, 2003, vol. 81, # 6, p. 709 - 722]
[2]Jeffery, Tuyet; Ferber, Benoît [Tetrahedron Letters, 2003, vol. 44, # 1, p. 193 - 197]

40
[ 123-11-5 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 83 percent / methanol / 0.5 h / 20 °C 2.1: t-BuOK / toluene / 1 h / 0 - 20 °C 2.2: 79 percent / Aliquat(R) 336; meso-tetraphenylporphyrin iron chloride; P(OMe)3 / toluene / 48 h / 40 °C

Reference： [1]Aggarwal, Varinder K.; Fulton, J. Robin; Sheldon, Chris G.; De Vicente, Javier [Journal of the American Chemical Society, 2003, vol. 125, # 20, p. 6034 - 6035]

41
[ 7311-34-4 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 66 percent / acetic anhydride; Et₃N / 5 h / 90 °C 2: quinoline; copper chromite / 1 h / 210 °C
	Multi-step reaction with 2 steps 1: tetrahydrofuran / -78 - 20 °C 2: 92 percent / bis(acetonitrile)palladium(II) chloride / CH₂Cl₂ / 14 h / 20 °C
	Multi-step reaction with 2 steps 1: Methyltriphenylphosphonium bromide; sodium hydride / tetrahydrofuran; mineral oil / 20 °C / Inert atmosphere 2: sodium acetate; palladium diacetate / methanol / 12 h / 20 °C / Inert atmosphere

Multi-step reaction with 2 steps 1: oxalyl dichloride; Triphenylphosphine oxide / chloroform / 2 h / 45 °C 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,2-dichlorotetramethylsilane / 5,5-dimethyl-1,3-cyclohexadiene / 3 h / 130 °C / Inert atmosphere

Reference： [1]Solladié, Guy; Pasturel-Jacopé, Yacine; Maignan, Jean [Tetrahedron, 2003, vol. 59, # 18, p. 3315 - 3321]
[2]Yu, Jinquan; Gaunt, Matthew J.; Spencer, Jonathan B. [Journal of Organic Chemistry, 2002, vol. 67, # 13, p. 4627 - 4629]
[3]Schmidt, Bernd; Elizarov, Nelli; Berger, René; Hölter, Frank [Organic and Biomolecular Chemistry, 2013, vol. 11, # 22, p. 3674 - 3691]
[4]An, Jie; Tang, Xiaoping; Moore, Joshua; Lewis, William; Denton, Ross M. [Tetrahedron, 2013, vol. 69, # 41, p. 8769 - 8776]

42
[ 696-62-8 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: KF; n-Bu₄NCl / bis(dibenzylideneacetone)palladium / toluene / 20 °C 2: KF; n-Bu₄NCl; K₂CO₃ / bis(dibenzylideneacetone)palladium / toluene; dimethylformamide; H₂O / 70 °C

Reference： [1]Jeffery, Tuyet; Ferber, Benoît [Tetrahedron Letters, 2003, vol. 44, # 1, p. 193 - 197]

43
[ 2150-37-0 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 93.3 percent / N₂H₄*H₂O / 3 h / Heating 2.1: 75.4 percent / K₃[Fe(CN)6]; PEG-400; NH₃ / toluene; H₂O / 4 h / 10 - 20 °C 3.1: NaOMe; tetrabutylammonium iodide / dimethylformamide / 1 h / 20 °C 3.2: 60.7 percent / dimethylformamide / 8 h / 40 °C
	Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran 2: magnesium / tetrahydrofuran 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 4: phosphoric acid / toluene / 5 h / Reflux
	Multi-step reaction with 4 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 25 °C / Cooling with ice 1.2: 8 h / 20 °C 2.1: pyridine; thionyl chloride / diethyl ether / 20 °C / Cooling with ice 3.1: 4 h / 130 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.25 h / Reflux

	Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / diethyl ether / 6 h / 20 °C / Inert atmosphere 2: Dess-Martin periodane / dichloromethane / 0 °C / Inert atmosphere 3: Methyltriphenylphosphonium bromide; sodium hydride / tetrahydrofuran; mineral oil / 20 °C / Inert atmosphere 4: sodium acetate; palladium diacetate / methanol / 12 h / 20 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 11 h / 0 - 20 °C 2.1: phosphorus tribromide / dichloromethane / 2 h / 0 °C 3.1: 7 h / 135 °C 4.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C 4.2: 17 h / 0 - 20 °C

Reference： [1]Shen, Zhen Lu; Zhuo, Guang Lan; Jiang, Xuan Zhen [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 11, p. 2395 - 2398]
[2]Jian, Yujuan; Sun, Gaojun; Li, Jiaming; Su, Dan; Li, Chuanrun; Zhong, Guochen [Chinese Journal of Chemistry, 2011, vol. 29, # 7, p. 1423 - 1428]
[3]Davis, Matthew C.; Groshens, Thomas J. [Tetrahedron Letters, 2012, vol. 53, # 27, p. 3521 - 3523]
[4]Schmidt, Bernd; Elizarov, Nelli; Berger, René; Hölter, Frank [Organic and Biomolecular Chemistry, 2013, vol. 11, # 22, p. 3674 - 3691]
[5]Ao, Junli; Chen, Yuanmou; Xu, Xiaoling; Zhang, Xu; Yu, Yue; Yu, Peng; Hua, Erbing [Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 2092 - 2098]

44
[ 2746-25-0 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 10 h / Heating 2.1: NaOMe; tetrabutylammonium iodide / dimethylformamide / 1 h / 20 °C 2.2: 60.7 percent / dimethylformamide / 8 h / 40 °C
	Multi-step reaction with 2 steps 1.1: 85.3 percent / toluene / 12 h / Heating 2.1: n-BuLi / tetrahydrofuran / -78 °C 2.2: 3.08 g / tetrahydrofuran
	Multi-step reaction with 2 steps 1: 130 °C 2: NaOCH₃ / dimethylformamide / 1 h / 20 °C

Multi-step reaction with 2 steps 1.1: water / 5 h / 80 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran-d8 / 0.17 h / 0 - 20 °C / Inert atmosphere 2.2: 3 h / 28 °C / Inert atmosphere

Reference： [1]Shen, Zhen Lu; Zhuo, Guang Lan; Jiang, Xuan Zhen [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 11, p. 2395 - 2398]
[2]Pettit, George R.; Grealish, Matthew P.; Jung, M. Katherine; Hamel, Ernest; Pettit, Robin K.; Chapuis, J.-Charles; Schmidt, Jean M. [Journal of Medicinal Chemistry, 2002, vol. 45, # 12, p. 2534 - 2542]
[3]Wang, Mingfu; Jin, Yi; Ho, Chi-Tang [Journal of Agricultural and Food Chemistry, 1999, vol. 47, # 10, p. 3974 - 3977]
[4]El-Deeb, Ibrahim Yussif; Funakoshi, Tatsuya; Shimomoto, Yuya; Matsubara, Ryosuke; Hayashi, Masahiko [Journal of Organic Chemistry, 2017, vol. 82, # 5, p. 2630 - 2640]

45
[ 105-13-5 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 95 percent / PBr₃ / CH₂Cl₂ / 3 h / 20 °C 2.1: 10 h / Heating 3.1: NaOMe; tetrabutylammonium iodide / dimethylformamide / 1 h / 20 °C 3.2: 60.7 percent / dimethylformamide / 8 h / 40 °C
	Multi-step reaction with 2 steps 1.1: 100 percent / gaseous HBr / benzene / 1 h / 78 °C 2.1: triethyl phosphate / 130 °C 2.2: 87 percent / NaOMe / dimethylformamide / 20 - 100 °C
	Multi-step reaction with 3 steps 1: thionyl chloride / diethyl ether / 2 h / 0 - 10 °C 2: chloroform / Reflux 3: sodium hydroxide / dichloromethane / 0.67 h / 0 °C

Reference： [1]Shen, Zhen Lu; Zhuo, Guang Lan; Jiang, Xuan Zhen [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 11, p. 2395 - 2398]
[2]Lu; Cai; Fang; Zhou; Liu; Wu, Longmin M. [Pharmazie, 2002, vol. 57, # 7, p. 474 - 478]
[3]Shen, Wei; Mao, Jianfeng; Sun, Juan; Sun, Minjie; Zhang, Can [Medicinal Chemistry Research, 2013, vol. 22, # 4, p. 1630 - 1640]

46
[ 22255-22-7 ]
[ 4179-19-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: O₃ / CH₂Cl₂; methanol / -78 °C 1.2: 60 percent / Ph₃P / CH₂Cl₂; methanol / 0.5 h 2.1: 87 percent / H₂ / 10 percent Pd/C / ethanol / 20 °C

Reference： [1]Fronza, Giovanni; Fuganti, Claudio; Serra, Stefano; Cisero, Marco; Koziet, Joseph [Journal of agricultural and food chemistry, 2002, vol. 50, # 10, p. 2748 - 2754]

47
[ 22255-22-7 ]
[ 5406-18-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: O₃ / CH₂Cl₂; methanol / -78 °C 1.2: 73 percent / Ph₃P / CH₂Cl₂; methanol / 0.5 h 2.1: 76 percent / CH₂Cl₂ / 5 h / Heating 3.1: H₂ / 10 percent Pd/C / ethyl acetate / 20 °C 3.2: 76 percent / LiAlH₄ / tetrahydrofuran / 5 h / Heating

Reference： [1]Fronza, Giovanni; Fuganti, Claudio; Serra, Stefano; Cisero, Marco; Koziet, Joseph [Journal of agricultural and food chemistry, 2002, vol. 50, # 10, p. 2748 - 2754]

48
[ 22255-22-7 ]
[ 1080-05-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: O₃ / CH₂Cl₂; methanol / -78 °C 1.2: 60 percent / Ph₃P / CH₂Cl₂; methanol / 0.5 h 2.1: CH₂Cl₂ / 5 h / Heating 3.1: H₂ / 10 percent Pd/C / ethyl acetate / 20 °C 3.2: LiAlH₄ / tetrahydrofuran / 5 h / Heating

Reference： [1]Fronza, Giovanni; Fuganti, Claudio; Serra, Stefano; Cisero, Marco; Koziet, Joseph [Journal of agricultural and food chemistry, 2002, vol. 50, # 10, p. 2748 - 2754]

49
[ 22255-22-7 ]
[ 157065-53-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: O₃ / CH₂Cl₂; methanol / -78 °C 1.2: 60 percent / Ph₃P / CH₂Cl₂; methanol / 0.5 h 2.1: CH₂Cl₂ / 5 h / Heating 3.1: H₂ / 10 percent Pd/C / ethyl acetate / 20 °C 3.2: LiAlH₄ / tetrahydrofuran / 5 h / Heating 4.1: CCl₄; Ph₃P / 8 h / Heating

Reference： [1]Fronza, Giovanni; Fuganti, Claudio; Serra, Stefano; Cisero, Marco; Koziet, Joseph [Journal of agricultural and food chemistry, 2002, vol. 50, # 10, p. 2748 - 2754]

50
[ 22255-22-7 ]
[ 59623-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: O₃ / CH₂Cl₂; methanol / -78 °C 1.2: 73 percent / Ph₃P / CH₂Cl₂; methanol / 0.5 h 2.1: 76 percent / CH₂Cl₂ / 5 h / Heating 3.1: H₂ / 10 percent Pd/C / ethyl acetate / 20 °C 3.2: 76 percent / LiAlH₄ / tetrahydrofuran / 5 h / Heating 4.1: 78 percent / CCl₄; Ph₃P / 8 h / Heating

Reference： [1]Fronza, Giovanni; Fuganti, Claudio; Serra, Stefano; Cisero, Marco; Koziet, Joseph [Journal of agricultural and food chemistry, 2002, vol. 50, # 10, p. 2748 - 2754]

51
[ 705-76-0 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Et₃N / tetrahydrofuran / 1 h / 0 - 20 °C 2: 33 percent / Li, naphthalene / tetrahydrofuran / 2 h / 0 °C 3: dimethylsulfoxide / 2 h / Heating
	Multi-step reaction with 3 steps 1: pyridine; thionyl chloride / diethyl ether / 20 °C / Cooling with ice 2: 4 h / 130 °C / Inert atmosphere 3: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.25 h / Reflux
	Multi-step reaction with 3 steps 1: Dess-Martin periodane / dichloromethane / 0 °C / Inert atmosphere 2: Methyltriphenylphosphonium bromide; sodium hydride / tetrahydrofuran; mineral oil / 20 °C / Inert atmosphere 3: sodium acetate; palladium diacetate / methanol / 12 h / 20 °C / Inert atmosphere

	Multi-step reaction with 3 steps 1.1: phosphorus tribromide / dichloromethane / 2 h / 0 °C 2.1: 7 h / 135 °C 3.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C 3.2: 17 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane / 0.25 h / 0 - 20 °C 2: bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 1,3-bis-(diphenylphosphino)propane; potassium <i>tert</i>-butylate / 1,4-dioxane / 12 h / 200 °C / Inert atmosphere; Glovebox; Schlenk technique; Sealed tube
	Multi-step reaction with 3 steps 1: thionyl chloride; N,N-dimethyl-formamide / diethyl ether 2: potassium iodide 3: sodium tert-pentoxide / tetrahydrofuran
	Multi-step reaction with 4 steps 1.1: thionyl chloride; N,N-dimethyl-formamide / diethyl ether / 25 °C / Cooling with ice 2.1: potassium iodide / 6 h / 130 °C 3.1: sodium tert-pentoxide / tetrahydrofuran / Reflux; Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 1 h / -80 °C 4.2: 1 h / -40 °C 4.3: 1 h / -80 °C
	Multi-step reaction with 3 steps 1: phosphorus tribromide; pyridine / dichloromethane / 3 h / 20 °C / Cooling with ice 2: tetrabutylammomium bromide / 160 °C 3: sodium hydride / N,N-dimethyl-formamide / 7 h / -10 - 0 °C
	Multi-step reaction with 3 steps 1: hydrogenchloride / water / Inert atmosphere 2: 10 h / 140 °C / Inert atmosphere 3: potassium hydroxide / tetrahydrofuran / 24 h / Inert atmosphere

Reference： [1]Alonso, Emma; Ramon, Diego J.; Yus, Miguel [Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 417 - 421]
[2]Davis, Matthew C.; Groshens, Thomas J. [Tetrahedron Letters, 2012, vol. 53, # 27, p. 3521 - 3523]
[3]Schmidt, Bernd; Elizarov, Nelli; Berger, René; Hölter, Frank [Organic and Biomolecular Chemistry, 2013, vol. 11, # 22, p. 3674 - 3691]
[4]Ao, Junli; Chen, Yuanmou; Xu, Xiaoling; Zhang, Xu; Yu, Yue; Yu, Peng; Hua, Erbing [Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 2092 - 2098]
[5]Xiao, Jing; Yang, Jia; Chen, Tieqiao; Han, Li-Biao [Chemical Communications, 2016, vol. 52, # 10, p. 2157 - 2160]
[6]Leláková, Veronika; Šmejkal, Karel; Jakubczyk, Karolina; Veselý, Ondřej; Landa, Přemysl; Václavík, Jiří; Bobáľ, Pavel; Pížová, Hana; Temml, Veronika; Steinacher, Theresa; Schuster, Daniela; Granica, Sebastian; Hanáková, Zuzana; Hošek, Jan [Food Chemistry, 2019, vol. 285, p. 431 - 440]
[7]Hošek, Jan; Leláková, Veronika; Bobál, Pavel; Pížová, Hana; Gazdová, Markéta; Malaník, Milan; Jakubczyk, Karolina; Veselý, Ondřej; Landa, Přemysl; Temml, Veronika; Schuster, Daniela; Prachyawarakorn, Vilailak; Pailee, Phanruethai; Ren, Gang; Zpurný, Filip; Oravec, Michal; Šmejkal, Karel [Journal of Natural Products, 2019, vol. 82, # 7, p. 1839 - 1848]
[8]Current Patent Assignee: SHANDONG BOK BIOLOGICAL TECH - CN110577464, 2019, A
[9]Jungong, Christian S.; Novikov, Alexei V. [Synthetic Communications, 2012, vol. 42, # 24, p. 3589 - 3597,9]

52
[ 104-92-7 ]
[ 7311-34-4 ]
[ 18107-18-1 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: 3,5-dimethoxybenzaldehdye; diazomethyl-trimethyl-silane With triphenylphosphine; copper(l) chloride In tetrahydrofuran; isopropyl alcohol at 60℃; Stage #2: 1-bromo-4-methoxy-benzene With triethylamine at 100℃; Further stages.;

Reference： [1]Lebel, Helene; Ladjel, Chehla; Brethous, Lise [Journal of the American Chemical Society, 2007, vol. 129, # 43, p. 13321 - 13326]

53
tricarbonyl-[1-(η6-3,5-dimethoxy-4-trimethylsilylphenyl)-2-(4'-methoxyphenyl)ethylene]chromium(0) [ No CAS ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With iodine In diethyl ether to soln. of Cr(CO)3C6H2(TMS)(OCH3)2CHCHC6H4OCH3 in AcOEt/Et2O added diiodine; mixt. stirred for 12 h at 20°C and Et2O added; soln. washed with satd. soln. of NaCl; dried with MgSO4 and concd. in vac.;

Reference： [1]Polunin; Schmalz [Russian Journal of Coordination Chemistry, 2004, vol. 30, # 4, p. 252 - 261]

54
[ 637-69-4 ]
[ 72470-95-2 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	With palladium diacetate; sodium acetate In benzonitrile at 25℃; for 12h;

Reference： [1]Moro, Angélica Venturini; Cardoso, Flávio Sega P.; Correia, Carlos Roque D. [Tetrahedron Letters, 2008, vol. 49, # 39, p. 5668 - 5671]

55
[ 1070879-03-6 ]
[ 7311-34-4 ]
[ 22255-22-7 ]
[ 112998-09-1 ]
[ 94608-23-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₂₆H₂₃O₄PS With sodium hydroxide In methanol for 0.0833333h; Stage #2: 3,5-dimethoxybenzaldehdye In methanol at 20℃;

Reference： [1]Location in patent: experimental part Huo, Congde; He, Xun; Tak, Hang Chan [Journal of Organic Chemistry, 2008, vol. 73, # 21, p. 8583 - 8586]

56
[ 696-62-8 ]
[ 40243-87-6 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium acetate; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 130℃; for 16h; Inert atmosphere;
60%	With zirconia-supported palladium; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 5h; Inert atmosphere;
56%	With ethanol; potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Nobre, Sabrina M.; Muniz, Mauro N.; Seferin, Marcus; Da Silva, Wagner M.; Monteiro, Adriano L. [Applied Organometallic Chemistry, 2011, vol. 25, # 4, p. 289 - 293]
[2]Location in patent: experimental part Borate, Hanumant B.; Dumbre, Deepa K.; Wakharkar, Radhika D.; Choudhary, Vasant R. [Journal of Chemical Research, 2008, # 9, p. 495 - 499]
[3]Shirakawa, Eiji; Zhang, Xuejing; Hayashi, Tamio [Angewandte Chemie - International Edition, 2011, vol. 50, # 20, p. 4671 - 4674]

57
[ 21960-26-9 ]
[ 705-76-0 ]
[ 22255-22-7 ]
[ 94608-23-8 ]

Yield	Reaction Conditions	Operation in experiment
	With nickel In tetrahydrofuran for 12h; Reflux; optical yield given as %de;
12 % de	at 70℃; for 1h; diastereoselective reaction;	4 Application of Rucat for Wittig Type Olefination Reaction General procedure: 50 mL round bottom flask was charged with Rucat (0.250 g), alcohol (0.1 mol) and phosphorus ylide (0.11 mol) was added to the reaction mixture. The combined reaction mass was allowed to react at 70 °C for 1 h. Again, after removing all the volatile organic impurities from the reaction mass, product was isolated by ether washing (5 × 2 mL). The diastereomeric selectivity was calculated using 1H NMR spectroscopic analyses. After the successful isolation of product, catalytic system was further reduced under hydrogen atmosphere (4 bar) at 50 °C for 3 h before going to the next catalytic run. Sequential addition of reactants was carried out as per above mentioned protocol for the same.

Reference： [1]Location in patent: body text Alonso, Francisco; Riente, Paola; Yus, Miguel [Tetrahedron Letters, 2009, vol. 50, # 25, p. 3070 - 3073]
[2]Srivastava, Vivek [Catalysis Letters, 2017, vol. 147, # 3, p. 693 - 703]

58
(4-(methoxy)benzyl)triethylphosphonium bromide [ No CAS ]
[ 7311-34-4 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: (4-(methoxy)benzyl)triethylphosphonium bromide In water at 20℃; for 0.25h; Stage #2: With sodium hydroxide In water for 0.0333333h; Stage #3: 3,5-dimethoxybenzaldehdye In water at 70℃; for 3h; optical yield given as %de;

Reference： [1]McNulty, James; Das, Priyabrata [European Journal of Organic Chemistry, 2009, # 24, p. 4031 - 4035]

59
[ 705-76-0 ]
[ 3462-97-3 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (4-methoxybenzyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; Stage #2: 3,5-dimethoxybenzyl alcohol With 4,4'-di-tert-butylbiphenyl; lithium; nickel dichloride In tetrahydrofuran; hexane for 12h; Inert atmosphere; Reflux; Stage #3: With iodine In hexane for 48h; Reflux;

Reference： [1]Alonso, Francisco; Riente, Paola; Yus, Miguel [European Journal of Organic Chemistry, 2009, # 34, p. 6034 - 6042]

60
[ 705-76-0 ]
[ 3462-97-3 ]
[ 22255-22-7 ]
[ 94608-23-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (4-methoxybenzyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; Stage #2: 3,5-dimethoxybenzyl alcohol With 4,4'-di-tert-butylbiphenyl; lithium; nickel dichloride In tetrahydrofuran; hexane for 12h; Inert atmosphere; Reflux; optical yield given as %de;

Reference： [1]Alonso, Francisco; Riente, Paola; Yus, Miguel [European Journal of Organic Chemistry, 2009, # 34, p. 6034 - 6042]

61
[ 24131-30-4 ]
[ 105-13-5 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (3,5-dimethoxybenzyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; Stage #2: 4-Methoxybenzyl alcohol With 4,4'-di-tert-butylbiphenyl; lithium; nickel dichloride In tetrahydrofuran; hexane for 8h; Inert atmosphere; Reflux; Stage #3: With 2,2'-azobis(isobutyronitrile); diphenyldisulfane In tetrahydrofuran for 8h; Reflux;

Reference： [1]Alonso, Francisco; Riente, Paola; Yus, Miguel [European Journal of Organic Chemistry, 2009, # 34, p. 6034 - 6042]

62
[ 24131-30-4 ]
[ 105-13-5 ]
[ 22255-22-7 ]
[ 94608-23-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (3,5-dimethoxybenzyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; Stage #2: 4-Methoxybenzyl alcohol With 4,4'-di-tert-butylbiphenyl; lithium; nickel dichloride In tetrahydrofuran; hexane for 8h; Inert atmosphere; Reflux; optical yield given as %de;

Reference： [1]Alonso, Francisco; Riente, Paola; Yus, Miguel [European Journal of Organic Chemistry, 2009, # 34, p. 6034 - 6042]

63
[ 696-62-8 ]
[ 1229971-81-6 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With tetrabutyl ammonium fluoride; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In tetrahydrofuran at 20 - 25℃; for 1h; Inert atmosphere;

Reference： [1]Sore, Hannah F.; Blackwell, David T.; MacDonald, Simon J. F.; Spring, David R. [Organic Letters, 2010, vol. 12, # 12, p. 2806 - 2809]

64
[ 22255-22-7 ]
[ 1228308-14-2 ]
[ 1228308-19-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With toluene-4-sulfonic acid In dichloromethane at 50℃; for 2h; Inert atmosphere;

Reference： [1]Nicolaou; Kang, Qiang; Wu, T. Robert; Lim, Chek Shik; Chen, David Y.-K. [Journal of the American Chemical Society, 2010, vol. 132, # 21, p. 7540 - 7548]

65
[ 637-69-4 ]
[ 91-52-1 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate / N,N-dimethyl acetamide / 8 h / 120 °C / Inert atmosphere 2: silver(I) acetate; potassium carbonate / N,N-dimethyl acetamide / 4 h / 160 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate / N,N-dimethyl acetamide / 8 h / 120 °C / Inert atmosphere 2: silver(I) acetate; potassium carbonate / N,N-dimethyl acetamide / 4 h / 160 °C / Inert atmosphere

Reference： [1]Mochida, Satoshi; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Organic Letters, 2010, vol. 12, # 24, p. 5776 - 5779]
[2]Mochida, Satoshi; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3024 - 3033]

66
[ 1300738-84-4 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	With silver(I) acetate; potassium carbonate In N,N-dimethyl acetamide at 160℃; for 4h; Inert atmosphere;
	With silver(I) acetate; potassium carbonate In N,N-dimethyl acetamide at 160℃; for 4h; Inert atmosphere;

Reference： [1]Mochida, Satoshi; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Organic Letters, 2010, vol. 12, # 24, p. 5776 - 5779]
[2]Location in patent: experimental part Mochida, Satoshi; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3024 - 3033]

67
[ 6652-32-0 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: magnesium / tetrahydrofuran 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3: phosphoric acid / toluene / 5 h / Reflux
	Multi-step reaction with 2 steps 1: 4 h / 130 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.25 h / Reflux
	Multi-step reaction with 2 steps 1: potassium iodide 2: sodium tert-pentoxide / tetrahydrofuran

	Multi-step reaction with 3 steps 1.1: potassium iodide / 6 h / 130 °C 2.1: sodium tert-pentoxide / tetrahydrofuran / Reflux; Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran / 1 h / -80 °C 3.2: 1 h / -40 °C 3.3: 1 h / -80 °C
	Multi-step reaction with 2 steps 1: 10 h / 140 °C / Inert atmosphere 2: potassium hydroxide / tetrahydrofuran / 24 h / Inert atmosphere

Reference： [1]Jian, Yujuan; Sun, Gaojun; Li, Jiaming; Su, Dan; Li, Chuanrun; Zhong, Guochen [Chinese Journal of Chemistry, 2011, vol. 29, # 7, p. 1423 - 1428]
[2]Davis, Matthew C.; Groshens, Thomas J. [Tetrahedron Letters, 2012, vol. 53, # 27, p. 3521 - 3523]
[3]Leláková, Veronika; Šmejkal, Karel; Jakubczyk, Karolina; Veselý, Ondřej; Landa, Přemysl; Václavík, Jiří; Bobáľ, Pavel; Pížová, Hana; Temml, Veronika; Steinacher, Theresa; Schuster, Daniela; Granica, Sebastian; Hanáková, Zuzana; Hošek, Jan [Food Chemistry, 2019, vol. 285, p. 431 - 440]
[4]Hošek, Jan; Leláková, Veronika; Bobál, Pavel; Pížová, Hana; Gazdová, Markéta; Malaník, Milan; Jakubczyk, Karolina; Veselý, Ondřej; Landa, Přemysl; Temml, Veronika; Schuster, Daniela; Prachyawarakorn, Vilailak; Pailee, Phanruethai; Ren, Gang; Zpurný, Filip; Oravec, Michal; Šmejkal, Karel [Journal of Natural Products, 2019, vol. 82, # 7, p. 1839 - 1848]
[5]Jungong, Christian S.; Novikov, Alexei V. [Synthetic Communications, 2012, vol. 42, # 24, p. 3589 - 3597,9]

68
[ 54900-97-9 ]
[ 123-11-5 ]
[ 22255-22-7 ]
[ 94608-23-8 ]

Yield	Reaction Conditions	Operation in experiment
	Alkaline conditions;
4.762 % de	Stage #1: 3,5-dimethoxybenzyltriphenylphosphonium chloride With lithium hydroxide In isopropyl alcohol at 20℃; for 1h; Stage #2: 4-methoxy-benzaldehyde In isopropyl alcohol at 60℃; for 10h; Overall yield = 92 %; Overall yield = 237 g;	4; 5; 6 Example 6 A method for preparing 3,4',5-trimethoxystilbene, the process of which is: 449 g of phosphorus ylide was added to 700 mL of isopropanol, 23.9 g (1.0 mol) of lithium hydroxide was added, and the mixture was stirred at room temperature for 1h, and then 129.7 g (0.95 mol) of p-methoxybenzaldehyde in isopropanol solution (100 mL) was added dropwise. After the addition, the reaction was heated to 60 ° C for 10 h. After the reaction was completed, water was added to quench the reaction, and ethyl acetate was extracted three times (3×200 mL), and the ethyl acetate phase was washed successively with 200 mL of saturated sodium chloride solution and anhydrous sodium sulfate. Dry, filter, and concentrate the organic phase to about 50 mL, add 150 mL of petroleum ether, place in the refrigerator for 24 h, filter, and concentrate the filtrate under reduced pressure to give a colorless oil of 237.0 g.Z: E = 1.1:1), yield 92%.

Reference： [1]Location in patent: scheme or table Jo, Geunhyeong; Hyun, Jiye; Hwang, Doseok; Lee, Young Han; Koh, Dongsoo; Lim, Yoongho [Magnetic Resonance in Chemistry, 2011, vol. 49, # 6, p. 374 - 377]
[2]Current Patent Assignee: JIANGCHU UNIV OF TECHNOLOGY; JINGCHU UNIVERSITY OF TECHNOLOGY - CN108689805, 2018, A Location in patent: Paragraph 0035-0040

69
[ 22255-22-7 ]
[ 676596-82-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	With N-Bromosuccinimide In dichloromethane at 25℃; for 1h; Inert atmosphere;
88%	With N-Bromosuccinimide In dichloromethane at 25℃; for 1h; Inert atmosphere; regioselective reaction;	4 Monobrominated Permethylated Resveratrol (9) Permethylated resveratrol (8,, 1.10 g,, 4.07 mmol,, 1.0 equiv) was dissolved in CH2C12 (40 mL) and an initial portion of NBS (0.362 g,, 2.04 mmol,, 0.5 equiv) was added at 25 °c. The resultant reaction mixturewas stirred for 30 mm at 25 °c,, at which time a second portion of NBS (0.362 g,, 2.04 mmol,, 0.5 equiv) was added. After stirring for an additional 30 mm at 25 °c,, the reaction contents were quenched with saturated aqueous NaHcO3 (25 mL) poured into water (10 mL) and extracted with EtOAc (3 x 30 mL) . The combinedorganic extracts were then washed with water (30 mL) and brine (30 mL) dried (MgSO4) filtered, and concentrated. The resultant cruder yellow oil was purified by flash column chromatography (silica gel, hexanes/EtOAc, 3:1) to afford the desired monobrominated material (9, 1.25 g, 88% yield) as an off-white solid. 9: Rf = 0.61 (silica gel, EtOAc/hexanes, 1:1); IR(film) max 3002, 2937, 2836, 1719, 1589, 1511, 1454, 1415, 1341,1286, 1252, 1203, 1163, 1082, 1023, 962, 827 cm’; ‘H NMR (300MHZ, cDcl3) 7.50 (d, J = 8.7 HZ, 2 H), 7.41 (d, J = 16.2 HZ, 1H), 6.98 (d, J = 16.2 HZ, 1 H), 6.91 (d, J = 9.0 HZ, 2 H), 6.80(d, J = 2.7 HZ, 1 H), 6.42 (d, J = 2.7 HZ, 1 H), 3.88 (s, 3 H), 3.86 (s 3 H), 3.83 (s, 3 H); ‘3C NMR (75 MHz, CDC13) 159.6,159.5, 156.8, 138.9, 131.1, 129.7, 128.1, 125.8, 114.1, 104.9,102.4, 98.7, 56.3, 55.5, 55.3; HRMS (FAB) calcd for C17H17BrO3[Mi] 348.0361, found 348.0362.

Reference： [1]Snyder, Scott A.; Thomas, Stephen B.; Mayer, Agathe C.; Breazzano, Steven P. [Angewandte Chemie - International Edition, 2012, vol. 51, # 17, p. 4080 - 4084]
[2]Current Patent Assignee: COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK - WO2013/49364, 2013, A1 Location in patent: Page/Page column 39; 43; 44

70
[ 22255-22-7 ]
[ 1093400-52-2 ]

Yield	Reaction Conditions	Operation in experiment
20%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 8h;
	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃;

Reference： [1]Orsini, Fulvia; Verotta, Luisella; Klimo, Karin; Gerhäuser, Clarissa [Archiv der Pharmazie, 2016, vol. 349, # 6, p. 414 - 427]
[2]Location in patent: experimental part Valdameri, Glaucio; Pereira Rangel, Luciana; Spatafora, Carmela; Guitton, Jerome; Gauthier, Charlotte; Arnaud, Ophelie; Ferreira-Pereira, Antonio; Falson, Pierre; Winnischofer, Sheila M. B.; Rocha, Maria E. M.; Tringali, Corrado; Pietro, Attilio Di [ACS Chemical Biology, 2012, vol. 7, # 2, p. 322 - 330]

71
[ 22255-22-7 ]
7-(3,5-dimethoxyphenyl)-1,3-dimethoxynaphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With 12-tungstophosphoric acid hydrate In 1,2-dichloro-ethane for 24h; Reflux;	1,3-Dimethoxy-7-(3,5-dimethoxyphenyl)naphthalene (7) A round-bottomed flask (100 mL) equipped with magnetic stirring bar was charged with 1 (3.45 g, 13 mmol), phosphotungstic acid hydrate (1 g, 0.3 mmol, 2 mol %) and 1,2-dichloroethane (100 mL). The mixture was refluxed for 24 h. After cooling to rt the mixture was filtered. The filtrate was washed with H2O followed by saturated aqueous NaHCO3 and finally brine. Next the filtrate was treated with anhydrous MgSO4 and decolorizing charcoal. The solvent was rotary evaporated leaving an oil (2.24 g). Silica gel chromatography of the product mixture (hexane/EtOAc : 9/1) gave compound 7 which slowly crystallized (810 mg, 43 %). Mp 90-91 °C [lit.song 89 °C]. 1H NMR (CDCl3): δ 8.36 (s, 1H), 7.77-7.66 (m, 2H), 7.29 (dd, J = 8.5 and 7.4 Hz, 1H), 6.87 (d, J = 2.3 Hz, 2H), 6.52 (d, J = 1.7 Hz, 1H), 6.48 (t, J = 2.8 Hz, 2H), 3.99 (s, 3H), 3.93 (s, 3H), 3.88 (s, 6H); 13C NMR (CDCl3): δ 161.30, 158.63, 157.04, 143.93, 135.79, 134.69, 127.12, 126.71, 122.02, 120.34, 105.75, 99.19, 98.17, 97.94, 55.75, 55.63, 55.52. Elemental analysis calculated for C20H20O4: C, 74.06; H, 6.21. Found: C, 74.19; H, 6.11.

Reference： [1]Davis, Matthew C.; Groshens, Thomas J. [Tetrahedron Letters, 2012, vol. 53, # 27, p. 3521 - 3523]

72
[ 22255-22-7 ]
resformicol B hexamethyl ether [ No CAS ]
resformicol A hexamethyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 12-tungstophosphoric acid hydrate In 1,2-dichloro-ethane for 4h; Reflux;	1,3-Dimethoxy-7-(3,5-dimethoxyphenyl)naphthalene (7) General procedure: A round-bottomed flask (100 mL) equipped with magnetic stirring bar was charged with 1 (3.45 g, 13 mmol), phosphotungstic acid hydrate (1 g, 0.3 mmol, 2 mol %) and 1,2-dichloroethane (100 mL). The mixture was refluxed for 24 h. After cooling to rt the mixture was filtered. The filtrate was washed with H2O followed by saturated aqueous NaHCO3 and finally brine. Next the filtrate was treated with anhydrous MgSO4 and decolorizing charcoal. The solvent was rotary evaporated leaving an oil (2.24 g). Silica gel chromatography of the product mixture (hexane/EtOAc : 9/1) gave compound 7 which slowly crystallized (810 mg, 43 %).

Reference： [1]Davis, Matthew C.; Groshens, Thomas J. [Tetrahedron Letters, 2012, vol. 53, # 27, p. 3521 - 3523]

73
[ 17275-82-0 ]
[ 22255-22-7 ]

Reference： [1]Synthetic Communications,2012,vol. 42,p. 3589 - 3597,9

74
[ 22255-22-7 ]
[ 42206-94-0 ]

Reference： [1]Synthetic Communications,2012,vol. 42,p. 3589 - 3597,9

75
[ 1352169-60-8 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With 1,2-dibromo-1,1,2,2-tetrachloroethane; alumina-supported potassium hydroxide In tetrahydrofuran; <i>tert</i>-butyl alcohol at 20℃; for 8h; stereoselective reaction;

Reference： [1]Soiderman, Stefan C.; Schwan, Adrian L. [Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10978 - 10984]

76
[ 40243-87-6 ]
[ 459-64-3 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
74%	With sodium acetate; palladium diacetate In methanol at 20℃; for 12h; Inert atmosphere;

Reference： [1]Schmidt, Bernd; Elizarov, Nelli; Berger, René; Hölter, Frank [Organic and Biomolecular Chemistry, 2013, vol. 11, # 22, p. 3674 - 3691]

77
[ 637-69-4 ]
[ 25245-27-6 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With C₃₃H₃₃N₂⁽¹⁺⁾*Cl^(1-); palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide for 2h; Inert atmosphere; Sealed tube; Heating;
72%	With 3-(anthracen-9-ylmethyl)-1-(3-(3,6-dichloro-9H-carbazol-9-yl)-2-hydroxypropyl)-1H-imidazol-3-ium chloride; palladium diacetate; triethylamine In acetonitrile at 120℃; for 24h; Schlenk technique; Inert atmosphere; chemoselective reaction;

Reference： [1]Srivastava, Vivek [Oriental Journal of Chemistry, 2012, vol. 28, # 4, p. 1859 - 1863]
[2]Girase, Tejpalsingh Ramsingh; Kapdi, Anant R. [Chemistry - An Asian Journal, 2019, vol. 14, # 15, p. 2611 - 2619]

78
[ 1446473-24-0 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 1,1'-bis-(diphenylphosphino)ferrocene; formic acid; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 80℃; for 0.333333h; Inert atmosphere;
91%	With 1,1'-bis-(diphenylphosphino)ferrocene; formic acid; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 20 - 80℃; for 0.333333h; Inert atmosphere;	trans-3,4',5-Trimethoxystilbene (8) To a round-bottomed flask (100 mL) equipped with magnetic stir bar was charged anhydrous DMF (6 mL) and triethylamine (960 mg, 9.5 mmol, 5 equiv). In dropwise fashion, 98% formic acid (437 mg, 9.5 mmol, 5 equiv) was added over 10 min. After allowing the mixture to cool to room temperature, a previously prepared solution of 7 (790 mg, 2 mmol) in anhydrous DMF (3 mL) was added in one portion followed by Pd(OAc)2 (21 mg, 0.09 mmol) and DPPF (105 mg, 0.18 mmol). A reflux condenser was equipped and the reaction mixture was heated under N2 to an internal temperature of 80° C. After 20 min the mixture had become dark and the reaction was complete by TLC analysis. The mixture was cooled to room temperature and partitioned between H2O (50 mL) and Et2O (50 mL). A rag layer formed and the mixture was filtered through medium filter paper. The organic layer was separated and washed with H2O (50 mL) and then brine (50 mL). After drying over anhydrous MgSO4, evaporation of the organic phase under reduced pressure left a pale brown oil that slowly crystallized (470 mg, 91%), mp. 55-57° C., lit 56-57° C. 1H NMR (CDCl3): δ 7.45 (d, J=8.9 Hz, 2H), 7.05 (d, J=16 Hz, 1H), 6.90 (d, J=16 Hz, 1H), 6.89 (d, J=8.6 Hz, 2H), 6.65 (d, J=2.2 Hz, 2H), 6.38 (t, J=2.5 Hz, 1H), 3.83 (s, 9H); 13C NMR (CDCl3): 161.20, 139.93, 130.16, 128.96, 128.02, 126.81, 114.37, 104.57, 99.86, 55.57, 55.53. Anal. Calcd for C17H18O3: C, 75.53; H, 6.71. Found: C, 75.53; H, 6.62. (E. Späth and K. Kromp, Ber., 74, 189 (1941)).

Reference： [1]Davis, Matthew C.; Parrish, Damon A.; Harvey, Benjamin G. [Organic Preparations and Procedures International, 2013, vol. 45, # 4, p. 304 - 313]
[2]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES - US8921614, 2014, B1 Location in patent: Page/Page column 5; 11

79
[ 21185-25-1 ]
[ 136269-35-7 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
123 mg	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,2-dichlorotetramethylsilane In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 3h; Inert atmosphere;	Synthesis of stilbenes (E)-1,3-Dimethoxy-5-(4-methoxystyryl)benzene; The following reagents were combined in the amounts indicated below in accordance with method b. 3,5-Dimethoxybenzaldehyde (166mg, 1.00mmol), oxalyl chloride (110μL, 1.30mmol) and triphenylphosphine oxide (21.0mg, 75.5μmol). Purification by flash column chromatography (silica, 10% Et2O/pet. ether) afforded 1-(dichloromethyl)-3,5-dimethoxybenzene as a colourless oil (195mg, 88%). The following reagents were combined in the amounts indicated below in accordance with method b. 4-Methoxybenzaldehyde (680mg, 5.00mmol), oxalyl chloride (550μL, 6.50mmol) and triphenylphosphine oxide (105mg, 37.7μmol). The solvent was removed in vacuo. The crude mixture was re-dissolved in xylene (5.0mL) and then 1-(dichloromethyl)-3,5-dimethoxybenzene (195mg, 0.880mol), 1,2-dichloro-1,1,2,2-tetramethyldisilane (2.23μL, 12.0mmol) and Pd(PPh3)4 (347mg, 0.300mmol) were added. The reaction mixture was heated to 130°C and stirred under N2 for 3h after which the cooled reaction was quenched with EtOAc (30.0mL) and filtered and the solvent was removed in vacuo. Purification by flash chromatography (silica, 10% EtOAc/pet. ether) afforded (E)-1,3-dimethoxy-5-(4-methoxystyryl)benzene 6c as a white solid (123mg, 52%). Mp 52.6-54.5°C (reported39f 52-54°C); 1H NMR (400MHz, CDCl3) δ 7.49-7.44 (m, 2H, ArH), 7.06 (d, J=16.3Hz, 1H, CH=CH), 6.95-6.89 (m, 3H, ArH ×2 and CH=CH), 6.67 (d, J=2.3Hz, 2H, ArH), 6.40 (t, J=2.3Hz, 1H, ArH), 3.85 (s, 9H, OCH3 ×3); 13C NMR (100MHz, CDCl3) δ 161.1, 159.5, 139.8, 130.0, 128.8, 127.9, 126.7, 114.2, 104.4, 99.7, 55.4, 55.4; HRMS (ESI+) [M+Na+] C17H18NaO3 calcd293.1148, found 293.1135.

Reference： [1]An, Jie; Tang, Xiaoping; Moore, Joshua; Lewis, William; Denton, Ross M. [Tetrahedron, 2013, vol. 69, # 41, p. 8769 - 8776]

80
[ 7311-34-4 ]
[ 3462-97-3 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
30.8%	With sodium hydroxide In dichloromethane at 0℃; for 0.666667h;

Reference： [1]Shen, Wei; Mao, Jianfeng; Sun, Juan; Sun, Minjie; Zhang, Can [Medicinal Chemistry Research, 2013, vol. 22, # 4, p. 1630 - 1640]

81
[ 400608-31-3 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With water; 1,2-bis-(diphenylphosphino)ethane; cobalt(II) iodide; zinc In acetonitrile at 60℃; for 12h; Inert atmosphere; Schlenk technique;
79%	Stage #1: 1,3-dimethoxy-5-((4-methoxyphenyl)ethynyl)benzene With nickel(II) iodide; 1,1'-bis-(diphenylphosphino)ferrocene In 1,4-dioxane at 20℃; for 0.0333333h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogen In 1,4-dioxane at 100℃; for 18h; Autoclave;
71%	With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); hypophosphorous acid; acetic acid In water at 80℃; for 4h; Inert atmosphere;	1 4.1 A typical procedure for the Ni-catalyzed semihydrogenation of alkynes General procedure: Under N2 atmosphere, a mixture 0.2 mmol of diphenylacetylene, 3 equivs 50% H3PO2 aqueous solution (65 μL), and 3 mol% NiCl2dppp (3.3 mg) in 0.5 mL of AcOH was stirred at 80 °C for 4 h until diphenylacetylene was consumed as followed by GC. The volatiles were pumped off and the crude products were subject to purification by column chromatography on silica gel (silica gel size: 38-63 μm, 40 g; column size: 2 cm * 30 cm) using hexane as an eluent to obtain the pure 2a in 85% yield (30.6 mg, E/Z = 98/2).

54 mg

With water; potassium ethyl xanthogenate In N,N-dimethyl-formamide at 130℃; for 12h; Schlenk technique; stereoselective reaction;

Reference： [1]Li, Kangkui; Khan, Ruhima; Zhang, Xuexin; Gao, Yang; Zhou, Yongyun; Tan, Heng; Chen, Jingchao; Fan, Baomin [Chemical Communications, 2019, vol. 55, # 39, p. 5663 - 5666]
[2]Thiel, Niklas O.; Kaewmee, Benyapa; Tran Ngoc, Trung; Teichert, Johannes F. [Chemistry - A European Journal, 2020, vol. 26, # 7, p. 1597 - 1603]
[3]Chen, Tieqiao; Xiao, Jing; Zhou, Yongbo; Yin, Shuangfeng; Han, Li-Biao [Journal of Organometallic Chemistry, 2014, vol. 749, p. 51 - 54]
[4]Luo, Xianglin; Chen, Xiuwen; Chen, Lu; Zhang, Kun; Li, Yibiao [Chemical Communications, 2019, vol. 55, # 15, p. 2170 - 2173]

82
[ 400608-31-3 ]
[ 22255-22-7 ]
[ 94608-23-8 ]

Yield	Reaction Conditions	Operation in experiment
92 % de	With lithium aluminium tetrahydride In diethylene glycol dimethyl ether at 90 - 100℃; for 1h; Inert atmosphere;	(E/Z) 3',4,5'-trimethoxy-stilbene (5): To a solution of 200 mg(0.745 mmol) of 1,3-dimethoxy-5-(4-methoxy-phenylethynyl)-benzene in 6.0 mL of diglyme, under Ar stream 56.5 mg(1.49 mmol) of lithium aluminum hydride was added, and themixture was stirred and heated at 90-100 C for 1.0 h. The solutionwas quenched with 20 mL of cold EtOAc and 30 mL ofammonium chloride saturated solution. The aqueous layer wasextracted with EtOAc (2 15 mL). The combined organic layerwas dried (Na2SO4) and evaporated, and the residue was subjectedto the next step without purification. The HPLC analysisof the mixture gave an E/Z ratio of 96:4. The analysis was performedusing a column Synergi of 4 l hydro RP 80A, with amobile phase of methanol/acetonitrile/buffer (63:30:7), the bufferwas dibasic potassium phosphate/H3PO4 to pH of 6.8 to temperatureof 40 C.

Reference： [1]Lara-Ochoa, Francisco; Sandoval-Minero, Leticia C.; Espinosa-Pérez, Georgina [Tetrahedron Letters, 2015, vol. 56, # 44, p. 5977 - 5979]

83
[ 22255-22-7 ]
2,4-Dimethoxy-6-[(E)-2-(4-methoxy-phenyl)-vinyl]-phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 0.583333h; regioselective reaction;

Reference： [1]Cardullo, Nunzio; Spatafora, Carmela; Musso, Nicolò; Barresi, Vincenza; Condorelli, Daniele; Tringali, Corrado [Journal of Natural Products, 2015, vol. 78, # 11, p. 2675 - 2683]

84
[ 104-47-2 ]
[ 157843-81-7 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 1,3-bis-(diphenylphosphino)propane; potassium <i>tert</i>-butylate In 1,4-dioxane at 200℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube; stereoselective reaction;

Reference： [1]Xiao, Jing; Yang, Jia; Chen, Tieqiao; Han, Li-Biao [Chemical Communications, 2016, vol. 52, # 10, p. 2157 - 2160]

85
[ 22255-22-7 ]
(1S,2S)-1-(3',5'-dimethoxyphenyl)-2-(4''-methoxyphenyl)-1,2-dihydroxyethane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With methanesulfonamide; AD-mix β In water; <i>tert</i>-butyl alcohol at 0 - 20℃; for 24h;

Reference： [1]Orsini, Fulvia; Verotta, Luisella; Klimo, Karin; Gerhäuser, Clarissa [Archiv der Pharmazie, 2016, vol. 349, # 6, p. 414 - 427]

86
[ 22255-22-7 ]
(1R,2R)-1-(3',5'-dimethoxyphenyl)-2-(4''-methoxyphenyl)-1,2-dihydroxyethane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With methanesulfonamide; AD-mix-β In water; <i>tert</i>-butyl alcohol at 0 - 20℃;

Reference： [1]Orsini, Fulvia; Verotta, Luisella; Klimo, Karin; Gerhäuser, Clarissa [Archiv der Pharmazie, 2016, vol. 349, # 6, p. 414 - 427]

87
C₂₀H₂₂O₄Se [ No CAS ]
[ 13139-86-1 ]
[ 22255-22-7 ]
[ 94608-23-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₂₀H₂₂O₄Se With iron(III)-acetylacetonate; triethylamine In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 0.25h; Inert atmosphere; Stage #2: 4-methoxyphenyl magnesium bromide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 4h; Inert atmosphere; Overall yield = 57 %; Overall yield = 0.155 g;	3.4. Preparation of 3,4’,5-Trimethoxystilbene 6 To a two-necked 100 mL round bottomed flask under nitrogen, the dry solvent (NMP/THF 1:3, 20.0 mL), bis(3,5-dimethoxystyryl) selenide 3f (0.406 g, 1 mmol), Et3N (2.5 mL) and Fe(acac)3 (71 mg, 20 mol %) was added. The mixture was stirred at room temperature, and after 15 min a solution of the Grignard reagent from 1-bromo-4-methoxybenzene (5, 10 mmol; 10.0 mL of a 1 mol/L sol. in THF) was added dropwise. The reactions were monitored by TLC until total disappearance of the starting material 3f. After completion of the reaction, aqueous sat. NH4Cl (15.0 mL) was added and the reaction mixture was extracted with ethyl acetate (3 × 20.0 mL), the organic layer was washed with water and dried over MgSO4. After filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (ethyl acetate/hexanes, 10:90). 3,4’,5-Trimethoxystilbene 6: Yield: 0.155 g (57%) [42]; Whitish oil; Z-6: 1H-NMR (CDCl3, 400 MHz) δ (ppm): 7.11 (d, J = 8.7 Hz, 2H), 6.66 (d, J = 8.7 Hz, 2H), 6.42 (d, J = 12.0 Hz, 1H), 6.343 (d, J = 2.3 Hz, 2H), 6.337 (d, J = 12.0 Hz, 1H), 6.22 (t, J = 2.3 Hz, 1H), 3.66 (s, 3H), 3.56 (s, 6H). MS: m/z (rel. int.) 270 (M+, 100), 239 (23.6), 224 (15.6), 196 (7.9), 181 (4.9), 152 (7.8), 141 (4.7), 115 (6.0), 102 (1.2) 76 (2.9). E-6: 1H-NMR (CDCl3, 400 MHz) δ (ppm): 7.33 (d, J = 8.8 Hz, 2H), 6.94 (d, J = 16.2 Hz, 1H), 6.80 (d, J = 16.2 Hz, 1H), 6.78 (d, J = 8.8 Hz, 2H), 6.55 (d, J = 2.3 Hz, 2H), 6.28 (t, J = 2.3 Hz, 1H), 3.71 (s, 6H), 3.70 (s, 3H). MS: m/z (rel. int.) 270 (M+, 100), 239 (21.3), 224 (10.8), 196 (6.5), 181 (4.1), 152 (6.0), 141 (3.5), 115 (4.2), 102 (0.9) 76 (2.4). 13C-NMR (CDCl3, 100 MHz) δ (ppm): (Z + E) 160.9, 160.5, 159.3, 158.7, 139.6, 139.4, 130.2, 130.1, 129.8, 129.5, 128.65, 128.60, 127.7, 126.5, 114.1, 113.4, 106.5, 104.3, 99.8, 99.5, 55.22, 55.18, 55.1.

Reference： [1]Perin, Gelson; Barcellos, Angelita M.; Luz, Eduardo Q.; Borges, Elton L.; Jacob, Raquel G.; Lenardão, Eder J.; Sancineto, Luca; Santi, Claudio [Molecules, 2017, vol. 22, # 2]

88
[ 22255-22-7 ]
[ 58436-28-5 ]

Reference： [1]Journal of Natural Products,2017,vol. 80,p. 2001 - 2011

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	22255-22-7	MDL No. :	MFCD02093500
Formula :	C₁₇H₁₈O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GDHNBPHYVRHYCC-SNAWJCMRSA-N
M.W :	270.32	Pubchem ID :	5388063
Synonyms :	trans-trismethoxy Resveratrol;E-Resveratrol Trimethyl Ether;trans-3,5,4'-trimethoxystilbene;TMS;(E)-5-[2-(4-hydroxyphenyl)ethenyl]-1,3-benzene diol;MR-3;3,4',5-Trimethoxy-trans-stilbene;Tri-O-methylresveratrol

Num. heavy atoms :	20
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.18
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	81.29
TPSA :	27.69 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.03 cm/s

Log Po/w (iLOGP) :	3.58
Log Po/w (XLOGP3) :	4.11
Log Po/w (WLOGP) :	3.67
Log Po/w (MLOGP) :	3.01
Log Po/w (SILICOS-IT) :	4.14
Consensus Log Po/w :	3.7

[ CAS No. 22255-22-7 ] {[proInfo.proName]}

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[ 22255-22-7 ] Synthesis Path-Downstream 1~88

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[ 22255-22-7 ]

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Log S (ESOL) :	-4.22
Solubility :	0.0163 mg/ml ; 0.0000604 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.4
Solubility :	0.0108 mg/ml ; 0.00004 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.39
Solubility :	0.00111 mg/ml ; 0.00000409 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.4

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 22255-22-7 ] {[proInfo.proName]}

Quality Control of [ 22255-22-7 ]

Related Doc. of [ 22255-22-7 ]

Product Details of [ 22255-22-7 ]

Calculated chemistry of [ 22255-22-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 22255-22-7 ]

Application In Synthesis of [ 22255-22-7 ]

[ 22255-22-7 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 22255-22-7 ]

Aryls

Alkenes

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 22255-22-7 ]