Name: 10309-37-2|(S,E)-4-(3,7-Dimethyl-3-vinylocta-1,6-dien-1-yl)phenol|96%
Brand: Ambeed
SKU: A182762
Rating: 97 (26 reviews)

1
[ 10309-37-2 ]
[ 10309-38-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 5% Pd(II)/C(eggshell); hydrogen In methanol for 3h;
98%	With palladium on activated charcoal; hydrogen In methanol	4.1.2.13. Synthesis of 4-(3-ethyl-3,7-dimethyloctyl)phenol (14) The title compound was prepared by hydrogenation of methanolic solution of 1 (1.0 mmol, 25 mL) at 35 psi with Pd/C to afford 14 in 98% yield. 1H NMR (200 MHz, CDCl3): δ 0.80-0.89 (12H, m), 1.12-1.61 (11H, m), 2.41 (2H, m, Ph-CH2-), 6.74 (2H, d, J = 8.3 Hz, 2× Ar-H), 7.03 (2H, d, J = 8.3 Hz, 2× Ar-H). 13C NMR (100 MHz): δ 8.27, 21.67, 24.48, 27.97, 29.47, 31.66, 35.30, 39.32, 40.20, 41.62, 115.27, 129.32, 136.1, 153.51. IR: 825, 1021, 1170, 1230, 1381, 1462, 1513, 1612, 2867, 2930, 2957, 3356 cm-1. MS at m/z 261 (M+ - 1).
93%	With palladium on activated charcoal; hydrogen In methanol at 20℃; for 24h; Inert atmosphere;	Compound 14 To a solution of bakuchiol (1.0 mmol) in MeOH (0.5M),Pd/C (1.0 mmol) was added at RT. The reaction mixture was degassed andmaintained under H2(g) atmosphere for 24hr. The reaction was monitored by TLCand LCMS. The resulting reaction mixture was filtered through celite and washedwith EtOAc (25 mL). The filtrate was concentrated in vacuo. The crude mixturewas purified on silica gel column chromatography (Hex/EtOAc, 9:1) to provide the compound 14.[α]D25:(-) 11.2; 1H NMR (400 MHz, Chloroform-d) δ 7.08 - 6.98 (m, 2H), 6.75 (d, J = 8.4 Hz, 2H), 2.47 - 2.37(m, 2H), 1.48 - 1.39 (m, 2H), 1.35 - 1.24 (m, 5H), 1.23 - 1.18 (m, 3H), 1.15 (q, J = 6.7 Hz, 2H), 0.92 -0.84 (m, 12H). 13C NMR (101 MHz, CDCl3) δ 153.40, 135.90, 129.28, 115.11, 41.58, 40.04, 39.10,35.14, 31.58, 31.50, 29.34, 27.93, 24.49, 22.69, 22.65, 21.18, 14.11, 7.99. HRMS (ESI-TOF) calculatedfor C18H30O ([M- H]+): 261.2219, found: 261.2223 (93% yield).

With hydrogen In acetic acid

Reference： [1]Location in patent: experimental part Mallepally V. Reddy; Niranjan Thota; Payare L. Sangwan; Pankaj Malhotra; Furqan Ali; Inshad A. Khan; Swapandeep S. Chimni; Koul, Surrinder [European Journal of Medicinal Chemistry, 2010, vol. 45, # 7, p. 3125 - 3134]
[2]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]
[3]Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 75 - 80]
[4]Mehta,G. et al. [Tetrahedron, 1973, vol. 29, p. 1119 - 1125]

2
[ 10309-37-2 ]
[ 108-24-7 ]
[ 43010-46-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With pyridine at 20℃; for 5h;
90.6%	With dmap In dichloromethane at 20℃;	3.4. General Procedure for the Synthesis of (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl) Phenyl SubstitutedCarboxylic Esters 3-6 General procedure: Compounds 3-6 were synthesized from compound 1 with an appropriate alkanoic anhydrideor acyl chloride in the presence of a catalytic amount of N,N-dimethylaminopyridine with 5 mLdichloromethane (DCM) as solvent. Reactions were monitored by TLC. After the reaction wascomplete, the mixture was poured in ice water and the resulting oily material, which was waterinsoluble, was separated and dissolved in DCM. Then the organic layer was washed with water fortwice, then dried by anhydrous calcium chloride and concentrated under reduced pressure. The acylderivatives were purified by silica gel column chromatography with a 40:1 n-hexane:ethyl acetatemixture as eluent to give compounds 3-6. The yields, Rf (n-hexane:ethyl acetate = 10:1) and the spectraldata of compounds 3-6 are given below. (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)phenyl acetate (3). The yield was 90.6%. Rf = 0.70. 1H-NMR(CDCl3) δ 7.38-7.32 (m, 2H, Ar-H), 7.04-6.99 (m, 2H, Ar-H), 6.30 (d, J = 16.2 Hz, 1H, 1-ene-H), 6.16 (d,J = 16.2 Hz, 1H, 2-ene-H), 5.87 (dd, J = 17.5, 10.7 Hz, 1H, 3-ethenyl-H), 5.10 (dd, J = 7.8, 6.4 Hz, 1H,6-ene-H), 5.03 (ddd, J = 18.7, 14.1, 1.2 Hz, 2H, 3-ethenyl-2H), 2.29 (s, 3H, -COCH3), 1.95 (dd, J = 16.2,7.7 Hz, 2H, -CH2-), 1.67 (s, 3H, -CH3), 1.58 (s, 3H, -CH3), 1.53-1.46 (m, 2H, -CH2-), 1.20 (s, 3H, 3-CH3).13C-NMR (CDCl3) δ 169.5, 149.6, 145.7, 138.2, 135.8, 131.4, 127.0 (2C), 126.3, 124.7, 121.6 (2C), 112.1,42.7, 41.2, 25.7, 23.3, 23.2, 21.1, 17.7. ESI-MS: m/z, [M + H]+ 299.2.
	With pyridine

11 mg

With pyridine

Reference： [1]Location in patent: experimental part Mallepally V. Reddy; Niranjan Thota; Payare L. Sangwan; Pankaj Malhotra; Furqan Ali; Inshad A. Khan; Swapandeep S. Chimni; Koul, Surrinder [European Journal of Medicinal Chemistry, 2010, vol. 45, # 7, p. 3125 - 3134]
[2]Wu, Cheng-Zhu; Liu, Da-Chuan; Guo, Xing; Dai, Yiqun; Ma, Tao; Li, Hong-Mei; Huo, Qiang [Molecules, 2018, vol. 23, # 3]
[3]Mehta,G. et al. [Tetrahedron, 1973, vol. 29, p. 1119 - 1125]
[4]Wu, Cheng-Zhu; Hong, Seong Su; Cai, Xing Fu; Dat, Nguyen Tien; Nan, Ji-Xing; Hwang, Bang Yeon; Lee, Jung Joon; Lee, Dongho [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 8, p. 2619 - 2623]

3
[ 10309-37-2 ]
[ 74-88-4 ]
[ 10309-44-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate In acetone for 8h; Reflux;
95%	With potassium carbonate In benzene at 20 - 80℃; for 36h; Inert atmosphere;	Etherification Reaction: compounds 10-13 General procedure: To a solution of Bakuchiol (1.0 mmol) in benzene (0.5M), K2CO3 (3.0 mmol) and methyl iodide orbenzyl bromide (4.0 mmol) were added at RT under an inert gas atmosphere. Then, the reaction wasstirred for 36hr under refluxing conditions (80°C). Then, the reaction mixture was filtered through celiteand washed with EtOAc (15 mL). The resulting mixture was quenched with 1N HCl (15 mL), washedwith saturated brine solution (25 mL) and H2O (15 mL). The mixture was extracted EtOAc (3 × 15 mL),the combined organic layer was dried over MgSO4 and filtered. The filtrate was concentrated in vacuoand purified by silica gel column chromatography (Hex/EtOAc, 49:1) to afford the desired compound.Compound 10. [α]D25: (+) 24.0; 1H NMR (400 MHz, Chloroform-d) δ 7.31 (d,J = 8.8 Hz, 2H), 6.85 (d, J = 8.9 Hz, 2H), 6.28 (d, J = 16.2 Hz, 1H), 6.11 -6.03 (m, 1H), 5.90 (ddd, J = 17.4, 10.8, 1.0 Hz, 1H), 5.17 - 5.09 (m, 1H), 5.08- 4.96 (m, 2H), 3.81 (d, J = 0.9 Hz, 3H), 1.97 (q, J = 7.5 Hz, 2H), 1.69 (s, 3H),1.59 (s, 3H), 1.55 - 1.47 (m, 2H), 1.21 (s, 3H). 13C NMR (101 MHz, CDCl3) δ158.73, 145.97, 135.79, 131.24, 130.70, 127.13, 126.53, 124.81, 113.89,111.83, 55.26, 42.52, 31.59, 25.68, 22.65, 17.62, 14.11. HRMS (ESI-TOF) calculated for C19H26O ([MH]+):269.1906, found: 269.1900 (95% yield).
93%	With potassium carbonate In acetone for 8h; Reflux;	4.1.2.9. Synthesis of 1-methoxy-4-(3,7-dimethyl-3-vinylocta-1,6-dienyl)benzene (10) Bakuchiol (2 mmol) was dissolved in acetone (5 mL) and anhydrous K2CO3 (3 mmol) was added followed by 2 mmol of methyl iodide. The mixture was allowed to reflux for 8 h. The reaction mixture was cooled, filtered, and evaporated. The product was purified by flash chromatography using hexane:EtOAc (19:1) as the eluent to afford 10 in 93% yield. 1H NMR (500 MHz, CDCl3): δ 1.21 (3H, s, -C(CHCH2)CH3), 1.51 (2H, m, -C(CH3)CH2CH2-), 1.59 and 1.69 (3H each, s, C(CH3)2), 1.96 (2H, m, -CH2CH), 3.80 (3H, s, -OCH3), 5.03 (2H, m, -C(CHCH2)CH3), 5.12 (1H, t, J = 7.28 Hz, -CHC), 5.89 (1H, dd, J = 10.95, 17.18 Hz,-C(CHCH2)), 6.08 (1H, d, J = 16.18 Hz, Ar-CHCH-), 6.28 (1H, d, J = 16.18 Hz, Ar-CHCH-), 6.85 (2H, d, J = 8.21 Hz, 2× Ar-H), 7.31 (2H, d, J = 8.21 Hz, 2× Ar-H). 13C NMR (125 MHz): δ 19.09, 24.70, 24.83, 27.15, 42.77, 43.98, 56.73, 113.3, 115.3, 126.29, 128.01, 128.61, 132.16, 132.71, 137.26, 147.45, 160.21. IR: 814, 912, 970, 1037, 1174, 1248, 1462, 1510, 1608, 1632, 2854, 2915, 2965, 3384 cm-1. MS at m/z 293 (M+ + Na).

90%	With potassium carbonate In acetone for 8h; Heating;
	With calcium oxide In dimethyl sulfoxide Ambient temperature;
	With sodium hydride In tetrahydrofuran for 6h; Heating;
	With sodium hydride In tetrahydrofuran 1.) r.t., 0.5 h, 2.) reflux, 6 h; Yield given;
	With potassium carbonate In N,N-dimethyl-formamide

Reference： [1]Location in patent: experimental part Mallepally V. Reddy; Niranjan Thota; Payare L. Sangwan; Pankaj Malhotra; Furqan Ali; Inshad A. Khan; Swapandeep S. Chimni; Koul, Surrinder [European Journal of Medicinal Chemistry, 2010, vol. 45, # 7, p. 3125 - 3134]
[2]Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 75 - 80]
[3]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]
[4]Chen, Hongli; Du, Xiaolong; Tang, Wei; Zhou, Yu; Zuo, Jianping; Feng, Huijin; Li, Yuanchao [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 5, p. 2403 - 2411]
[5]Mehta,G. et al. [Tetrahedron, 1973, vol. 29, p. 1119 - 1125]
[6]Banerji, Asoke; Chintalwar, Gajanan J. [Phytochemistry, 1983, vol. 22, # 9, p. 1945 - 1948]
[7]Bhan; Soman; Dev [Agricultural and Biological Chemistry, 1980, vol. 44, # 7, p. 1483 - 1487]
[8]Takano; Shimazaki; Ogasawara [Tetrahedron Letters, 1990, vol. 31, # 23, p. 3325 - 3326]

4
[ 10309-44-1 ]
[ 10309-37-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With methyl magnesium iodide at 160℃; for 0.166667h;
91%	With methyl magnesium iodide In diethyl ether at 0 - 180℃; for 0.25h; Inert atmosphere;
90%	With methyl magnesium iodide In diethyl ether at 180℃; for 0.166667h; Inert atmosphere;	19 (S,E)-4-(3,6-Dimethyl-3-vinylhepta-1,5-dien-1-yl)phenol (Bakuchiol) To a solution of 20 (151mg, 0.56mmol) in 5mL of Et2O was added a solution of MeMgI in Et2O (0.28mL, 0.84mmol, 3.0M in Et2O). The solvent was removed under reduced pressure, and the residue was heated under Ar at 180°C for 10min. The mixture was cooled to rt, and the reaction mixture was quenched with 10mL of satd NH4Cl aqsolution. The product was extracted with AcOEt (10mL×3). The combined extracts were washed with brine and dried (Na2SO4). The solvent was removed under reduced pressure, and the crude product was purified by column chromatography (Petroleum ether/ethyl acetate 15:1) to afford Bakuchiol as colorless oil (129mg, 90%). Rf (Petroleum ether/ethyl acetate=10:1) 0.53. [α]D27.5 +24.9 (c 0.98, CHCl3). [lit.:8-10 [α]D20 +29.9 (c 1.01, CHCl3)]. 1H NMR (400MHz, CDCl3) δ 7.24 (d, J=8.5Hz, 2H), 6.76 (d, J=8.5Hz, 2H), 6.25 (d, J=16.2Hz, 1H), 6.05 (d, J=16.2Hz, 1H), 5.88 (dd, J=17.2, 10.8Hz, 1H), 5.11 (t, J=7.1Hz, 1H), 5.02 (m, 2H), 1.95 (m, 2H), 1.67 (s, 3H), 1.58 (s, 3H), 1.49 (m, 2H), 1.19 (s, 3H). 13C NMR (100MHz, CDCl3) δ 154.5, 145.9, 135.7, 131.3, 130.7, 127.3, 126.4, 124.7, 115.3, 111.8, 42.4, 41.2, 25.6, 23.2, 23.1, 17.6. ESI-MS: Calcdfor C18H25O+ [M+H]: 257.1, found: 257.2.

89%	With methyl magnesium iodide at 175℃; for 0.166667h;
89%	With methyl magnesium iodide at 175℃;
80%	With methyl magnesium iodide at 185℃; for 0.166667h; Inert atmosphere;

Reference： [1]Esumi, Tomoyuki; Yamamoto, Chihiro; Fukuyama, Yoshiyasu [Synlett, 2013, vol. 24, # 14, p. 1845 - 1847]
[2]Takao, Ken-Ichi; Shu, Sakamoto; Touati, Marianne Ayaka; Kusakawa, Yusuke; Tadano, Kin-Ichi [Molecules, 2012, vol. 17, # 11, p. 13330 - 13344]
[3]Xu, Qian-Qian; Zhao, Qun; Shan, Guang-Sheng; Yang, Xi-Cheng; Shi, Qi-Yuan; Lei, Xinsheng [Tetrahedron, 2013, vol. 69, # 50, p. 10739 - 10746]
[4]Takano; Shimazaki; Ogasawara [Tetrahedron Letters, 1990, vol. 31, # 23, p. 3325 - 3326]
[5]Location in patent: scheme or table Esumi, Tomoyuki; Shimizu, Hiroyuki; Kashiyama, Akinori; Sasaki, Chizu; Toyota, Masao; Fukuyama, Yoshiyasu [Tetrahedron Letters, 2008, vol. 49, # 48, p. 6846 - 6849]
[6]Xiong, Yang; Zhang, Guozhu [Organic Letters, 2016, vol. 18, # 19, p. 5094 - 5097]

5
[ 10309-37-2 ]
[ 43010-52-2 ]
[ 10309-38-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In ethanol at 29℃; Yield given. Yields of byproduct given;

Reference： [1]Bhan; Soman; Dev [Agricultural and Biological Chemistry, 1980, vol. 44, # 7, p. 1483 - 1487]

6
[ 50-00-0 ]
[ 10309-37-2 ]
[ 1026776-51-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine; magnesium chloride In tetrahydrofuran at 90℃; for 5h; Inert atmosphere; regioselective reaction;	Compound 30 Under anhydrous conditions, Bakuchiol (10 mmol), MgCl2 (20mmol) and Et3N (25 mmol) were dissolved in THF (20 mL) under an inert atmosphere. Then, solid paraformaldehyde (30 mmol) was added and the mixturewas stirred under refluxing conditions (90°C) for 5hr. The reaction mixture wascooled to RT and quenched with H2O (10 mL). The reaction mixture was filteredthrough celite, acidified with HCl (2 N, 20 mL) and extracted with EtOAc (3 × 15 mL). The organiclayer was washed with brine (2 x 30 mL), dried over MgSO4, filtered and the solvent evaporated undervacuum. The residue was purified by silica gel column chromatography (Hex/EtOAc, 8.5:1.5), affordingthe pure compound 30. [α]D25: (+) 32.0; 1H NMR (400 MHz, Chloroform-d) δ 9.89 (s, 1H), 7.56 (dd, J =8.7, 2.3 Hz, 1H), 7.50 (d, J = 2.2 Hz, 1H), 6.94 (d, J = 8.6 Hz, 1H), 6.28 (d, J = 16.2 Hz, 1H), 6.12 (d, J= 16.3 Hz, 1H), 5.88 (dd, J = 17.5, 10.7 Hz, 1H), 5.11 (tt, J = 7.0, 1.5 Hz, 1H), 5.08 (s, 2H), 1.96 (q, J =7.5 Hz, 2H), 1.68 (d, J = 1.5 Hz, 3H), 1.58 (s, 3H), 1.56 - 1.47 (m, 2H), 1.21 (s, 3H). 13C NMR (101MHz, CDCl3) δ 196.59, 160.59, 145.49, 137.47, 134.46, 130.95, 125.24, 124.61, 120.43, 117.76,112.22, 42.63, 41.20, 31.57, 25.67, 23.23, 22.64, 17.63, 14.10. HRMS (ESI-TOF) calculated forC19H24O2 ([M - H]+): 283.1698, found: 283.1704 (85% yield).
62%	With triethylamine; magnesium chloride In tetrahydrofuran for 3h; Heating;

Reference： [1]Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 75 - 80]
[2]Chen, Hongli; Du, Xiaolong; Tang, Wei; Zhou, Yu; Zuo, Jianping; Feng, Huijin; Li, Yuanchao [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 5, p. 2403 - 2411]

7
[ 10309-37-2 ]
[ 1026776-58-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	With nickel(II) nitrate hexahydrate; toluene-4-sulfonic acid In acetone for 1h; Reflux;
70%	With nitric acid; acetic acid In cyclohexane at 48℃; for 0.166667h;
51.8%	With toluene-4-sulfonic acid; nickel(II) nitrate In acetone Reflux;	3.5. Synthesis of (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-2-nitrophenol (7) Compound 1 (0.5 mM) was dissolved in acetone (10 mL), then nickel (II) nitrate (1 mmol) anda catalytic amount of p-TSA (0.01 mmol) were added. The mixture was refluxed until compound1 was fully consumed, and then the acetone was removed under vacuum to get the crude product.After extraction with water and DCM, the organic layer was dried with anhydrous calcium chlorideovernight and concentrated under reduced pressure. The pure compound 7 was obtained by silica gelcolumn chromatography with n-hexane:ethyl acetate mixture (40:1) as eluent. The yield of compound7 was 51.8%. Rf = 0.85 (n-hexane:ethyl acetate = 10:1). 1H-NMR (CDCl3) δ 10.52 (s, 1H, Ar-OH), 8.04 (s,1H, Ar-H), 7.61 (dd, J = 8.3, 1.7 Hz, 1H, Ar-H), 7.10 (d, J = 8.7 Hz, 1H, Ar-H), 6.26 (d, J = 15.8 Hz, 1H,1-ene-H), 6.17 (d, J = 16.3 Hz, 1H, 2-ene-H), 5.87 (dd, J = 17.4, 10.6 Hz, 1H, 3-ethenyl-H), 5.15-5.09 (m,1H, 6-ene-H), 5.10-4.98 (m, 2H, 3-ethenyl-2H), 1.95 (dd, J = 16.4, 8.7 Hz, 2H, -CH2-), 1.68 (s, 3H, -CH3),1.58 (s, 3H, -CH3), 1.53 - 1.47 (m, 2H, -CH2-), 1.21 (s, 3H, -CH3). ESI-MS: m/z, [M + H]+ 302.3.

Reference： [1]Location in patent: experimental part Mallepally V. Reddy; Niranjan Thota; Payare L. Sangwan; Pankaj Malhotra; Furqan Ali; Inshad A. Khan; Swapandeep S. Chimni; Koul, Surrinder [European Journal of Medicinal Chemistry, 2010, vol. 45, # 7, p. 3125 - 3134]
[2]Chen, Hongli; Du, Xiaolong; Tang, Wei; Zhou, Yu; Zuo, Jianping; Feng, Huijin; Li, Yuanchao [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 5, p. 2403 - 2411]
[3]Wu, Cheng-Zhu; Liu, Da-Chuan; Guo, Xing; Dai, Yiqun; Ma, Tao; Li, Hong-Mei; Huo, Qiang [Molecules, 2018, vol. 23, # 3]

8
[ 10309-37-2 ]
[ 1026776-43-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sulfuric acid In 1,4-dioxane; water at 25℃; for 0.0166667h;
80%	With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone at 20℃; for 24h; Inert atmosphere; chemoselective reaction;	Compound 16 To a solution of acetone and H2O (1:1, v/v), bakuchiol (1 mmol)was added dropwise along with OsO4 catalyst (0.5 mmol, 4% wt in H2O) and NmethylmorpholineN-oxide (2 mmol) at RT for 24 hr. The reaction mixture wasmonitored by TLC and LCMS. The osmium catalyst was filtered off and theremaining mixture was filtered through celite. The mixture was extracted withEtOAc (3 × 15 mL), washed with NaCl (2 × 15 mL), dried over MgSO4 and concentrated in vacuo. Theresidue was chromatographed by silica gel column (Hex/EtOAc, 1:1) to afford corresponding diol 16. 1HNMR (400 MHz, Chloroform-d) δ 7.24 (d, J = 8.2 Hz, 2H), 6.77 (d, J = 8.2 Hz, 2H), 6.26 (d, J = 16.3Hz, 1H), 6.03 (d, J = 16.2 Hz, 1H), 5.87 (ddd, J = 17.5, 10.8, 3.9 Hz, 1H), 5.56 (s, 1H), 5.15 - 4.89 (m,2H), 4.12 (q, J = 7.1 Hz, 3H), 3.34 (d, J = 10.2 Hz, 1H), 2.05 (s, 3H), 1.93 - 1.81 (m, 1H), 1.55 - 1.42(m, 2H), 1.26 (s, 3H), 1.19 (m, 5H), 1.15 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 171.26, 155.00,145.73, 135.45, 130.46, 127.35, 126.75, 115.38, 112.23, 112.17, 60.43, 53.40, 42.30, 31.57, 26.57,23.27, 22.63, 21.03, 14.17. HRMS (ESI-TOF) calculated for C18H26O3 ([M - H]+): 289.1804, found:289.1808 (80% yield).

Reference： [1]Chen, Hongli; Du, Xiaolong; Tang, Wei; Zhou, Yu; Zuo, Jianping; Feng, Huijin; Li, Yuanchao [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 5, p. 2403 - 2411]
[2]Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 75 - 80]

9
[ 10309-37-2 ]
[ 1026776-42-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 6h;
80%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 25℃;
80%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 25℃; for 3h;	4.1.2.15. Synthesis of 12,13-epoxybakuchiol (16) Bakuchiol (5.0 mmol) was dissolved in 30 mL DCM at 0 °C and m-CPBA (5.5 mmol) in 60 mL DCM was added slowly. After being stirred for 3 h at 25 °C, aqueous saturated NaHSO3 solution added and the contents stirred for an additional 0.5 h. The reaction mixture was extracted with DCM and the organic layer was washed with water, dried, and evaporated. The product was purified by CC over silica gel using hexane:EtOAc (9:1) as the eluent to afford 16 in 80% yield. 1H NMR (500 MHz, CDCl3): δ 1.20 (3H, s, -C(CHCH2)CH3), 1.22 and 1.23 (3H each, s, C(CH3)2), 1.57 (4H, m, -C(CH3)CH2CH2-), 2.67 (1H, t, J = 6.0 Hz,-CH2-CH-), 5.03 and 5.06 (1H each, m, -C(CHCH2)CH3), 5.93 (1H, m, -CHCH2), 6.10 (1H, d, J = 16.2 Hz, Ar-CHCH-), 6.31 (1H, d, J = 16.2 Hz, Ar-CHCH-), 6.79 (2H, d, J = 8.5 Hz, 2× Ar-H), 7.31 (2H, d, J = 8.5 Hz, 2× Ar-H). 13C NMR (50 MHz): δ 18.3, 23.1, 23.2, 24.6, 37.9, 42.3, 57.8, 64.2, 112.0, 115.7, 127.7, 127.8, 129.8, 134.7, 146.4, 157.4. IR: 814, 912, 970, 1037, 1174, 1248, 1462, 1510, 1608, 1632, 2854, 2915, 2965, 3384. MS at m/z 271 (M+ - 1).

78%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 25℃; for 3h;
73%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; chemoselective reaction;	Compound 15 To a solution of bakuchiol (1.0 mmol) in CH2Cl2 (10 mL), m-CPBA (1.1 mmol) in CH2Cl2 was added over 5 minutes at 0°C. The reactionmixture was stirred for 3 hr at RT. The precipitate was filtered and washed withcold CH2Cl2 (10 mL). The filtrate was quenched with saturated solution ofNaHSO3(aq) (20 mL). The reaction mixture was extracted with CH2Cl2 (2×15 mL),the organic layer washed with H2O (20 mL), dried over MgSO4 and concentrated under reduced12pressure. The crude product was purified by silica gel column chromatography (Hex/EtOAc, 9:1) toprovide 15. [α]D25: (+) 17.8; 1H NMR (400 MHz, Chloroform-d) δ 7.23 (d, J = 8.6 Hz, 2H), 6.77 (d, J =8.6 Hz, 2H), 6.26 (d, J = 16.3 Hz, 1H), 6.08 - 5.97 (m, 1H), 5.86 (ddd, J = 17.5, 10.7, 1.5 Hz, 1H), 5.12- 4.96 (m, 2H), 2.73 (t, J = 5.9 Hz, 1H), 1.79 - 1.62 (m, 2H), 1.61 - 1.45 (m, 2H), 1.31 (d, J = 1.2 Hz,3H), 1.26 (s, 3H), 1.19 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 155.01, 145.49, 145.43, 135.13, 130.41,127.36, 126.94, 115.41, 112.29, 64.88, 58.77, 42.20, 37.50, 24.88, 24.19, 23.35, 18.66. HRMS (ESITOF)calculated for C18H24O2 ([M - H]+): 271.1698, found: 271.1703 (75% yield).
27.4%	Stage #1: bakuchiol With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; Stage #2: In dichloromethane Alkaline conditions;	3.8. Synthesis of 4-((3S,E)-3-(2-(3,3-dimethyloxiran-2-yl)ethyl)-3-methylpenta-1,4-dien-1-yl) phenol (11) Compound 1 (1.5 mmol) was dissolved in DCM (6 mL). 3-Chloroperoxybenzoic acid (m-CPBA,3 mmol) dissolved in 5 mL DCM was added dropwise to the solution under ice bath cooling, and thenthe mixture was stirred at room temperature for 4.5 h, until the reaction was complete as monitored byTLC. Saturated sodium bicarbonate was added and stirred for 1 h to neutralize the excess m-CPBA.After pouring into 250 mL water, the aqueous layer was extracted thrice with 90 mL dichloromethane(30 mL x 3). The combined dichloromethane layers were dried over anhydrous sodium sulfateovernight. Evaporation of the solvent gave a crude product, which was purified by silica gel columnchromatography with n-hexane:ethyl acetate mixture (10:1) as eluent to give the title compound in27.4% yield. Rf = 0.30 (n-hexane:ethyl acetate mixture = 10:1). 1H-NMR (CDCl3) δ 7.25-7.24 (m, 1H,Ar-H), 7.24-7.23 (m, 1H, Ar-H), 6.78-6.77 (m, 1H, Ar-H), 6.76-6.75 (m, 1H, Ar-H), 6.28-6.24 (m, 1H,1-ene-H), 6.07-6.01 (m, 1H, 2-ene-H), 5.89-5.83 (m, 1H, 3-ethenyl-H), 5.07-5.02 (m, 2H, 3-ethenyl-2H),2.71 (t, J = 5.7 Hz, 1H, 30-CH-), 1.58-1.54 (m, 6H, -CH3), 1.31-1.28 (m, 2H, -CH2-), 1.26-1.24 (m, 2H,-CH2-), 1.20 (s, 3H, -CH3). 13C-NMR (CDCl3) δ 154.8, 145.5, 135.2, 129.8, 127.4 (2C), 126.9, 115.4 (2C),112.2, 64.7, 58.5, 42.2, 37.5, 24.9, 24.2, 23.4, 18.7. ESI-MS: m/z, [M + H]+ 273.2.

Reference： [1]Location in patent: experimental part Cha, Mi-Ran; Choi, Chun Whan; Lee, Ji Young; Kim, Young Sup; Yon, Gyu Hwan; Choi, Sang-Un; Ryu, Shi Yong [Bulletin of the Korean Chemical Society, 2012, vol. 33, # 7, p. 2378 - 2380]
[2]Location in patent: experimental part Mallepally V. Reddy; Niranjan Thota; Payare L. Sangwan; Pankaj Malhotra; Furqan Ali; Inshad A. Khan; Swapandeep S. Chimni; Koul, Surrinder [European Journal of Medicinal Chemistry, 2010, vol. 45, # 7, p. 3125 - 3134]
[3]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]
[4]Chen, Hongli; Du, Xiaolong; Tang, Wei; Zhou, Yu; Zuo, Jianping; Feng, Huijin; Li, Yuanchao [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 5, p. 2403 - 2411]
[5]Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 75 - 80]
[6]Wu, Cheng-Zhu; Liu, Da-Chuan; Guo, Xing; Dai, Yiqun; Ma, Tao; Li, Hong-Mei; Huo, Qiang [Molecules, 2018, vol. 23, # 3]

10
[ 38449-25-1 ]
[ 10309-37-2 ]
[ 1028939-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h;	14 A solution of MAA (315 mg) and bakuchiol (220mg) in DCM (5ml) was treated with DCC (190 mg, 0.922mmol).followed by DMAP (1 mg). Resulting mixture was stirred at room temperature for 2 hrs. Evaporated solvent and the residue obtained was loaded on a SiO2 column and eluted with 100% CHCl3 to obtained the pure product (an oil). The yield obtained was 100 mg. The structural formula may be represented as formula XV. Mass [M+] m/z: 598.

Reference： [1]Current Patent Assignee: UNICHEM LABORATORIES LIMITED - WO2008/62436, 2008, A2 Location in patent: Page/Page column 16

11
[ 540-38-5 ]
[ 10309-37-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
64%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 7h; Inert atmosphere;	4.1.3. General procedure for preparation of compounds 18-22 by Heck coupling reaction General procedure: A mixture of substituted aromatic halide (1.2 equiv), bakuchiol (1.0 equiv) and K2CO3 (2 equiv) in dry DMF in presence of tetrakis (triphenylphosphine) palladium (O) complex was refluxed under N2 current at 140 °C for 7 h. The contents cooled, diluted with 5% HCl to attain pH 5, and extracted with diethyl ether (3 × 100 mL), the organic layer washed with water (2 × 50 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude product purified by CC over silica (60-120) with hexane:EtOAc mixture as the eluent to afford the required compound.

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

12
[ 696-62-8 ]
[ 10309-37-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
73%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 12h; Inert atmosphere; Microwave irradiation;	General Procedure for Pd(0) mediated Heck Reaction: compounds 51-54 General procedure: To a solution of aryl iodide (1.5 mmol), bakuchiol (1.0 mmol) in DMF (10 mL), K2CO3 (2.0 mmol), and the Pd(PPh3)4 catalyst (5 mol%) were added under anhydrous conditions. The reaction mixture was degassed and placed on a microwave reactor, and heated to 140°C for 12 hr. Then, the reaction mixture was cooled to RT and the precipitate filtered. The resultant mixture was washed with brine (35 mL) andH2O (4 × 30 mL). The organic layer was dried over anhydrous Na2SO4, evaporated under reduced pressure and the residue was purified by silica gel column chromatography (Hex/EtOAc, 9:1) to affordthe desired product. Compound 51. [α]D25: (-) 12.6; 1H NMR (400 MHz, Chloroform-d) δ7.34 - 7.29 (m, 2H), 7.27 (dd, J = 6.7, 1.7 Hz, 2H), 6.89 - 6.82 (m, 2H),6.82 - 6.75 (m, 2H), 6.32 (d, J = 4.9 Hz, 1H), 6.28 (d, J = 4.7 Hz, 1H),6.15 (d, J = 2.0 Hz, 1H), 6.11 (d, J = 2.0 Hz, 1H), 5.13 (t, J = 7.5 Hz, 1H),3.81 (d, J = 1.7 Hz, 3H), 2.01 (q, J = 8.0 Hz, 2H), 1.68 (s, 3H), 1.59 (m,5H), 1.29 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 158.75, 154.72, 136.09,136.05, 131.31, 130.68, 127.38, 127.18, 126.57, 126.51, 124.84, 115.36,113.92, 55.30, 41.78, 29.70, 25.70, 24.06, 23.37, 17.68. HRMS (ESI-TOF)calculated for C25H30O2 ([M + H]+): 363.2324, found: 363.2327 (73% yield).

Reference： [1]Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 75 - 80]

13
[ 10309-37-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
81%	With selenium(IV) oxide In tetrahydrofuran; water; acetic acid at 20℃; for 4h; Inert atmosphere;	Compound 24 Bakuchiol (0.5 g, 1.9 mmol) was dissolved inAcOH:H2O:THF (9:1:1). Then, SeO2 (432 mg, 3.8 mmol) was added andallowed to stirred for 4hr at RT. The reaction mixture was diluted with coldH2O and extracted with CH2Cl2 (2×10 mL). The combined organic layer waswashed with H2O (2×10 mL), dried over anhydrous Na2SO4 andconcentrated under reduced pressure. The residue was purified by silica gel column chromatography(Hex/EtOAc, 9:1) to afford the aldehyde 24 (0.3 g). [α]D25: (-) 18.74; 1H NMR (400 MHz, Chloroformd)δ 9.37 (s, 1H), 7.24 (d, J = 8.6 Hz, 2H), 6.82 (d, J = 8.6 Hz, 2H), 6.61 - 6.47 (m, 1H), 6.30 (d, J =16.3 Hz, 1H), 6.04 (d, J = 16.3 Hz, 1H), 5.90 (dd, J = 17.5, 10.7 Hz, 1H), 5.20 - 5.00 (m, 2H), 2.36 (q, J= 7.6 Hz, 2H), 1.74 (d, J = 1.3 Hz, 3H), 1.72 - 1.62 (m, 2H), 1.25 (s, 3H). 13C NMR (101 MHz, CDCl3)δ 195.40, 155.23, 155.07, 145.09, 139.14, 134.58, 130.26, 127.42, 127.38, 127.31, 115.47, 112.70,42.48, 39.57, 24.56, 23.41, 9.18. HRMS (ESI-TOF) calculated for C18H22O2 ([M + H]+): 271.1698,found: 2 71.1697 (81% yield).
67%	With selenium(IV) oxide; acetic acid In water at 20℃; for 4h;	4.1.2.14. Synthesis of 6-(4-hydroxystyryl)-2,6-dimethylocta-2,7-dienal (15) Bakuchiol (0.5 g, 1.9 mmol) was dissolved in a mixture of acetic acid and water (9:1), SeO2 (216 mg, 1.9 mmol) was added and the contents stirred for 4 h at 20 °C. The reaction mixture was diluted with ice-cold water and extracted with EtOAc (2 × 100 mL). The organic layer washed with water (2 × 50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to give crude product, which was purified on silica gel column using Pet. ether 60-80:EtOAc (9:1) as the eluent to afford 15 in 67% yield. 1H NMR (200 MHz, CDCl3): δ 1.25 (3H, s, -C(CHCH2)CH3), 1.64 (2H, m, -C(CH3)CH2CH2-), 1.72 (3H, s, C(CH3)), 2.01 (2H, m, -CH2CH), 4.99 (2H, m, -C(CHCH2)CH3), 5.89 (1H, dd, J = 17.3, 10.8 Hz, -C(CHCH2)), 6.02 (1H, d, J = 16.28 Hz, Ar-CHCH-), 6.28 (1H, d, J = 16.28 Hz, Ar-CHCH-), 6.50 (1H, t, J = 7.0 Hz, -CHC), 6.78 (2H, d, J = 8.56 Hz, 2× Ar-H), 7.24 (2H, d, J = 8.56 Hz, 2× Ar-H), 9.36 (1H, s, -CHO). 13C NMR (50 MHz): δ 18.5, 24.64, 24.73, 42.65, 43.8, 113.51, 115.56, 127.85, 129.68, 131.81, 137.33, 140.42, 147.35, 152.86, 155.6, 195.1. IR: 757, 1020, 1084, 1120, 1169, 1217, 1456, 1513, 1610, 1715, 2851, 2922, 3384 cm-1. MS at m/z 269 (M+ - 1).
65%	With selenium(IV) oxide; acetic acid In water at 20℃; for 4h;

Reference： [1]Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 75 - 80]
[2]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]
[3]Location in patent: experimental part Mallepally V. Reddy; Niranjan Thota; Payare L. Sangwan; Pankaj Malhotra; Furqan Ali; Inshad A. Khan; Swapandeep S. Chimni; Koul, Surrinder [European Journal of Medicinal Chemistry, 2010, vol. 45, # 7, p. 3125 - 3134]

14
[ 480438-57-1 ]
bakuchiol [ No CAS ]
4-{-3-(3-chloro-4-propoxystyryl)-3,7-dimethylocta-1,6-dienyl}phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With oxygen; palladium diacetate; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 7h;
49.6%	With oxygen; palladium diacetate; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 7h;	4.1.4. General procedure for preparation of compounds 23-25, 27 by oxidative Heck coupling reaction Bakuchiol dissolved in DMF (0.2 M) stirred at room temperature (<25 °C) and to the clear solution, substituted phenyl boronic acid (1.2 equiv) followed by a single addition of Na2CO3 and Pd(OAc)2 catalyst. The reaction flask fitted with an oxygen balloon, heated up to 100 °C with stirring for 7 h. The contents diluted with diethyl ether (20 mL), and washed with aqueous NaCl solution (2 × 25 mL). The organic layer dried over Na2SO4 and filtered. The filtrate concentrated under reduced pressure and the crude products purified by CC over silica gel (60-120 mesh) with EtOAc:Hexane mixture as the eluent to afford the appropriate compounds.

Reference： [1]Location in patent: experimental part Mallepally V. Reddy; Niranjan Thota; Payare L. Sangwan; Pankaj Malhotra; Furqan Ali; Inshad A. Khan; Swapandeep S. Chimni; Koul, Surrinder [European Journal of Medicinal Chemistry, 2010, vol. 45, # 7, p. 3125 - 3134]
[2]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

15
[ 10309-37-2 ]
[ 540-37-4 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
51.7%	With oxygen; palladium diacetate; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 7h;	4.1.4. General procedure for preparation of compounds 23-25, 27 by oxidative Heck coupling reaction Bakuchiol dissolved in DMF (0.2 M) stirred at room temperature (<25 °C) and to the clear solution, substituted phenyl boronic acid (1.2 equiv) followed by a single addition of Na2CO3 and Pd(OAc)2 catalyst. The reaction flask fitted with an oxygen balloon, heated up to 100 °C with stirring for 7 h. The contents diluted with diethyl ether (20 mL), and washed with aqueous NaCl solution (2 × 25 mL). The organic layer dried over Na2SO4 and filtered. The filtrate concentrated under reduced pressure and the crude products purified by CC over silica gel (60-120 mesh) with EtOAc:Hexane mixture as the eluent to afford the appropriate compounds.
49%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 7h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]
[2]Location in patent: experimental part Mallepally V. Reddy; Niranjan Thota; Payare L. Sangwan; Pankaj Malhotra; Furqan Ali; Inshad A. Khan; Swapandeep S. Chimni; Koul, Surrinder [European Journal of Medicinal Chemistry, 2010, vol. 45, # 7, p. 3125 - 3134]

16
[ 529-28-2 ]
[ 10309-37-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
52%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 7h; Inert atmosphere;	4.1.3. General procedure for preparation of compounds 18-22 by Heck coupling reaction General procedure: A mixture of substituted aromatic halide (1.2 equiv), bakuchiol (1.0 equiv) and K2CO3 (2 equiv) in dry DMF in presence of tetrakis (triphenylphosphine) palladium (O) complex was refluxed under N2 current at 140 °C for 7 h. The contents cooled, diluted with 5% HCl to attain pH 5, and extracted with diethyl ether (3 × 100 mL), the organic layer washed with water (2 × 50 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude product purified by CC over silica (60-120) with hexane:EtOAc mixture as the eluent to afford the required compound.

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

17
[ 696-62-8 ]
[ 10309-37-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
55%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 7h; Inert atmosphere;	4.1.3. General procedure for preparation of compounds 18-22 by Heck coupling reaction General procedure: A mixture of substituted aromatic halide (1.2 equiv), bakuchiol (1.0 equiv) and K2CO3 (2 equiv) in dry DMF in presence of tetrakis (triphenylphosphine) palladium (O) complex was refluxed under N2 current at 140 °C for 7 h. The contents cooled, diluted with 5% HCl to attain pH 5, and extracted with diethyl ether (3 × 100 mL), the organic layer washed with water (2 × 50 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude product purified by CC over silica (60-120) with hexane:EtOAc mixture as the eluent to afford the required compound.

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

18
[ 1765-93-1 ]
[ 10309-37-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
51%	With oxygen; palladium diacetate; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 7h;	4.1.4. General procedure for preparation of compounds 23-25, 27 by oxidative Heck coupling reaction Bakuchiol dissolved in DMF (0.2 M) stirred at room temperature (<25 °C) and to the clear solution, substituted phenyl boronic acid (1.2 equiv) followed by a single addition of Na2CO3 and Pd(OAc)2 catalyst. The reaction flask fitted with an oxygen balloon, heated up to 100 °C with stirring for 7 h. The contents diluted with diethyl ether (20 mL), and washed with aqueous NaCl solution (2 × 25 mL). The organic layer dried over Na2SO4 and filtered. The filtrate concentrated under reduced pressure and the crude products purified by CC over silica gel (60-120 mesh) with EtOAc:Hexane mixture as the eluent to afford the appropriate compounds.

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

19
[ 10309-37-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
86%	With toluene-4-sulfonic acid; nickel(II) nitrate In acetone Reflux;	4.1.2.10. Synthesis of 3-nitro,4-(3,7-dimethyl-3-vinylocta-1,6-dienyl) phenol (11) To a stirred solution of the bakuchiol (1 mmol) in acetone (15 mL) was added nickel (II) nitrate (1 mmol) followed by a catalytic amount of p-TSA (0.012 mmol) and the reaction mixture was refluxed until 1 was fully consumed. Acetone was removed under vacuum and the crude mass was partitioned between DCM and water. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was purified by CC over silica gel using hexane:EtOAc (49:1) as the eluent to furnish 11 in 86% yield. 1H NMR (200 MHz, CDCl3): δ 1.22 (3H, s, -C(CHCH2)CH3), 1.51 (2H, m, -C(CH3)CH2CH2-), 1.59 and 1.68 (3H each, s, C(CH3)2), 1.96 (2H, m, -CH2CH), 5.06 (3H, m, -C(CHCH2)CH3, -CH2CHC), 5.88 (1H, dd, J = 10.92, 17.22 Hz, -C(CHCH2)), 6.17 (1H, d, J = 16.18 Hz, Ar-CHCH-), 6.28 (1H, d, J = 16.18 Hz, Ar-CHCH-), 7.10 (1H, d, J = 8.62 Hz, Ar-H), 7.62 (1H, d, J = 8.62 Hz, Ar-H), 8.03 (1H, s, Ar-H). 13C NMR (50 MHz): δ 17.72, 23.19, 23.26, 25.76, 41.19, 42.82, 112.56, 120.05, 121.9, 124.60, 130.95, 131.58, 133.57, 135.07, 139.33, 145.23, 154.05. IR: 669, 762, 1019, 1078, 1216, 1322, 1404, 1422, 1537, 1626, 2854, 2924, 3020, 3377 cm-1. MS at m/z 300 (M+ - 1).

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

20
[ 10309-37-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: bakuchiol With mercury(II) diacetate; sodium hydroxide In tetrahydrofuran; water at 0℃; for 0.5h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water	4.1.2.16. Synthesis of 4-[2-{4-(2-hydroxypropan-2-yl)-1,2-dimethylcyclopentyl}vinyl]phenol (17) Bakuchiol (1.95 mmol) dissolved in THF:H2O (1:1) (10 mL) at 0 °C, added Hg(OAc)2 (0.625 g, 1.95 mmol), after stirring the solution for 10 min, 10% NaOH solution was added to the reaction mixture. Reaction mixture was further stirred for half an hour, followed by addition of NaBH4, reaction monitored through TLC. After the completion of the reaction, the contents neutralized with dilute HCl and extracted with EtOAc (3 × 100 mL). The combined organic layers washed with water (2 × 50 mL), and dried over anhydrous Na2SO4. The crude product purified by CC over silica gel using Hexane:EtOAc (9:1) as the eluent to afford 17 in 90% yield. 1H NMR (500 MHz, CDCl3): δ 0.95 (3H, d, J = 6.67 Hz, -CHCH3), 0.98 (3H, s, -C-CH3), 1.24 (6H, br s, -C-(CH3)2), 1.49 (1H, q, J = 8.6 Hz, 2.2 Hz, -CH), 1.59 (2H, m, -CH2), 1.72 (2H, m, CH-CH2-CH2) 1.87 (1H, m,-CH-(CH3)2OH), 6.03 (1H, d, J = 16.2 Hz, Ar-CHCH-), 6.24 (1H, d, J = 16.2 Hz, Ar-CHCH-), 6.76 (2H, d, J = 8.5 Hz, Ar-H), 7.22 (2H, d, J = 8.5 Hz, Ar-H). 13C NMR (125 MHz): δ 16.07, 18.48, 26.12, 27.68, 28.40, 39.80, 44.51, 48.20, 55.62, 74.27, 115.47, 125.81, 127.23, 130.58, 137.97, 154.98. IR: 757, 816, 854, 928, 968, 1021, 1164, 1237, 1379, 1451, 1512, 1608, 2927, 2963, 3360 cm-1. MS at m/z 273 (M+ - 1).

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

21
[ 10309-37-2 ]
[ 79-03-8 ]
[ 1361320-38-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	With dmap	4.1.2. General procedure for preparation of acyl derivatives of bakuchiol (2-9) General procedure: Compounds 2-9 were synthesized by treating bakuchiol 1 with appropriate alkanoic anhydride in presence of catalytic amount of N,N-dimethyl amino pyridine and the progress of reaction monitored by TLC. On completion of the reaction, the contents poured in ice water and the oily material separated and dissolved in DCM. The organic layer washed with water, dried over anhydrous calcium chloride and concentrated under reduced pressure. The acyl derivatives thus obtained were purified by column chromatography (CC) over silica gel 60-120 mesh, using hexane:Ethyl acetate mixture (49:1) as eluent to give compounds 2-9 in >90% overall yield. The spectral data of all the derivatives of 1 are given below.

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

22
[ 10309-37-2 ]
[ 638-29-9 ]
[ 1361320-40-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With dmap	4.1.2. General procedure for preparation of acyl derivatives of bakuchiol (2-9) General procedure: Compounds 2-9 were synthesized by treating bakuchiol 1 with appropriate alkanoic anhydride in presence of catalytic amount of N,N-dimethyl amino pyridine and the progress of reaction monitored by TLC. On completion of the reaction, the contents poured in ice water and the oily material separated and dissolved in DCM. The organic layer washed with water, dried over anhydrous calcium chloride and concentrated under reduced pressure. The acyl derivatives thus obtained were purified by column chromatography (CC) over silica gel 60-120 mesh, using hexane:Ethyl acetate mixture (49:1) as eluent to give compounds 2-9 in >90% overall yield. The spectral data of all the derivatives of 1 are given below.

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

23
[ 10309-37-2 ]
[ 142-61-0 ]
[ 1361320-41-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With dmap	4.1.2. General procedure for preparation of acyl derivatives of bakuchiol (2-9) General procedure: Compounds 2-9 were synthesized by treating bakuchiol 1 with appropriate alkanoic anhydride in presence of catalytic amount of N,N-dimethyl amino pyridine and the progress of reaction monitored by TLC. On completion of the reaction, the contents poured in ice water and the oily material separated and dissolved in DCM. The organic layer washed with water, dried over anhydrous calcium chloride and concentrated under reduced pressure. The acyl derivatives thus obtained were purified by column chromatography (CC) over silica gel 60-120 mesh, using hexane:Ethyl acetate mixture (49:1) as eluent to give compounds 2-9 in >90% overall yield. The spectral data of all the derivatives of 1 are given below.

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

24
[ 10309-37-2 ]
[ 112-13-0 ]
[ 1361320-43-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With dmap	4.1.2. General procedure for preparation of acyl derivatives of bakuchiol (2-9) General procedure: Compounds 2-9 were synthesized by treating bakuchiol 1 with appropriate alkanoic anhydride in presence of catalytic amount of N,N-dimethyl amino pyridine and the progress of reaction monitored by TLC. On completion of the reaction, the contents poured in ice water and the oily material separated and dissolved in DCM. The organic layer washed with water, dried over anhydrous calcium chloride and concentrated under reduced pressure. The acyl derivatives thus obtained were purified by column chromatography (CC) over silica gel 60-120 mesh, using hexane:Ethyl acetate mixture (49:1) as eluent to give compounds 2-9 in >90% overall yield. The spectral data of all the derivatives of 1 are given below.

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

25
bakuchiol [ No CAS ]
[ 42298-41-9 ]
4-{3-(3-formyl-4-methoxystyryl)-3,7-dimethylocta-1,6-dienyl}phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 7h; Inert atmosphere;	4.1.3. General procedure for preparation of compounds 18-22 by Heck coupling reaction General procedure: A mixture of substituted aromatic halide (1.2 equiv), bakuchiol (1.0 equiv) and K2CO3 (2 equiv) in dry DMF in presence of tetrakis (triphenylphosphine) palladium (O) complex was refluxed under N2 current at 140 °C for 7 h. The contents cooled, diluted with 5% HCl to attain pH 5, and extracted with diethyl ether (3 × 100 mL), the organic layer washed with water (2 × 50 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude product purified by CC over silica (60-120) with hexane:EtOAc mixture as the eluent to afford the required compound.

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

26
[ 10309-37-2 ]
[ 75-36-5 ]
[ 43010-46-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With dmap	4.1.2. General procedure for preparation of acyl derivatives of bakuchiol (2-9) General procedure: Compounds 2-9 were synthesized by treating bakuchiol 1 with appropriate alkanoic anhydride in presence of catalytic amount of N,N-dimethyl amino pyridine and the progress of reaction monitored by TLC. On completion of the reaction, the contents poured in ice water and the oily material separated and dissolved in DCM. The organic layer washed with water, dried over anhydrous calcium chloride and concentrated under reduced pressure. The acyl derivatives thus obtained were purified by column chromatography (CC) over silica gel 60-120 mesh, using hexane:Ethyl acetate mixture (49:1) as eluent to give compounds 2-9 in >90% overall yield. The spectral data of all the derivatives of 1 are given below.

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

27
[ 10309-37-2 ]
[ 141-75-3 ]
[ 1361320-39-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With dmap	4.1.2. General procedure for preparation of acyl derivatives of bakuchiol (2-9) General procedure: Compounds 2-9 were synthesized by treating bakuchiol 1 with appropriate alkanoic anhydride in presence of catalytic amount of N,N-dimethyl amino pyridine and the progress of reaction monitored by TLC. On completion of the reaction, the contents poured in ice water and the oily material separated and dissolved in DCM. The organic layer washed with water, dried over anhydrous calcium chloride and concentrated under reduced pressure. The acyl derivatives thus obtained were purified by column chromatography (CC) over silica gel 60-120 mesh, using hexane:Ethyl acetate mixture (49:1) as eluent to give compounds 2-9 in >90% overall yield. The spectral data of all the derivatives of 1 are given below.

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

28
[ 10309-37-2 ]
[ 111-64-8 ]
[ 1361320-42-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With dmap	4.1.2. General procedure for preparation of acyl derivatives of bakuchiol (2-9) General procedure: Compounds 2-9 were synthesized by treating bakuchiol 1 with appropriate alkanoic anhydride in presence of catalytic amount of N,N-dimethyl amino pyridine and the progress of reaction monitored by TLC. On completion of the reaction, the contents poured in ice water and the oily material separated and dissolved in DCM. The organic layer washed with water, dried over anhydrous calcium chloride and concentrated under reduced pressure. The acyl derivatives thus obtained were purified by column chromatography (CC) over silica gel 60-120 mesh, using hexane:Ethyl acetate mixture (49:1) as eluent to give compounds 2-9 in >90% overall yield. The spectral data of all the derivatives of 1 are given below.

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

29
[ 10309-37-2 ]
[ 112-67-4 ]
[ 1361320-44-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With dmap	4.1.2. General procedure for preparation of acyl derivatives of bakuchiol (2-9) General procedure: Compounds 2-9 were synthesized by treating bakuchiol 1 with appropriate alkanoic anhydride in presence of catalytic amount of N,N-dimethyl amino pyridine and the progress of reaction monitored by TLC. On completion of the reaction, the contents poured in ice water and the oily material separated and dissolved in DCM. The organic layer washed with water, dried over anhydrous calcium chloride and concentrated under reduced pressure. The acyl derivatives thus obtained were purified by column chromatography (CC) over silica gel 60-120 mesh, using hexane:Ethyl acetate mixture (49:1) as eluent to give compounds 2-9 in >90% overall yield. The spectral data of all the derivatives of 1 are given below.

Reference： [1]Location in patent: experimental part Majeed, Rabiya; Reddy, Mallepally V.; Chinthakindi, Praveen K.; Sangwan, Payare L.; Hamid, Abid; Chashoo, Gousia; Saxena, Ajit K.; Koul, Surrinder [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 55 - 67]

30
[ 358-23-6 ]
[ 10309-37-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridine; dmap In dichloromethane at 0℃; for 3h; Inert atmosphere;	Compound 12 To a solution of Bakuchiol (1.0 mmol) in CH2Cl2 (0.5M),pyridine (5.0 mmol), DMAP (0.1 mmol) was added at 0 oC. Then,trifluoromethanesulfonic anhydride (1.5 mmol) was added dropwise over15 min. The reaction was monitored by LCMS, TLC and was completed in3.0 hr. The reaction mixture was diluted with CH2Cl2 (10 mL), quenchedwith H2O (10 mL) and extracted with CH2Cl2 (3 × 15 mL). The combined organic layer was washedwith 1 N HCl solution (15 mL), brine solution (20 mL) and H2O (15 mL). After drying over Na2SO4, thesolvent was evaporated in vacuo and purified by silica gel column chromatography (Hex/EtOAc,9.5:0.5) to provide the pure product 12. [α]D25: (+) 32.4; 1H NMR (400 MHz, Chloroform-d) δ 7.41 (d, J= 8.7 Hz, 2H), 7.20 (d, J = 8.7 Hz, 2H), 6.31 (d, J = 16.2 Hz, 1H), 6.22 (dd, J = 16.2, 0.8 Hz, 1H), 5.87(ddd, J = 17.5, 10.7, 0.8 Hz, 1H), 5.14 - 5.09 (m, 1H), 5.09 - 4.99 (m, 2H), 1.95 (q, J = 7.4 Hz, 2H),1.67 (s, 3H), 1.58 (s, 3H), 1.57 - 1.47 (m, 2H), 1.21 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 148.25,145.16, 140.26, 138.30, 131.47, 127.56, 125.42, 124.50, 121.32, 112.44, 41.92, 27.15, 25.64, 24.69,23.17, 23.14, 17.61. HRMS (ESI-TOF) calculated for C19H23F3O3S ([M - H]+): 387.1242, found:387.1251 (92% yield).

Reference： [1]Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 75 - 80]

31
[ 10309-37-2 ]
[ 98-59-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate In benzene at 20℃; for 24h; Inert atmosphere;	Compound 13 To a solution of Bakuchiol (1.0 mmol) in benzene(0.5M), K2CO3 (3.0 mmol) and 4-methylbenzenesulfonyl chloride (1.5mmol) were added at RT under an argon atmosphere. The reaction wasallowed to stir at RT for 24 hr, monitored by TLC and LCMS. Theresulting reaction mixture was filtered through celite and washed withEtOAc (15 mL). The mixture was quenched with 1N HCl (15 mL), washed with a saturated brinesolution (25 mL) and H2O (15 mL). The reaction mixture was extracted with EtOAc (2 × 15 mL), driedover MgSO4, filtered and concentrated in vacuo. The crude compound was purified by silica gel columnchromatography (Hex/EtOAc, 40:1) to afford compound 13. [α]D25: (+) 18.0; 1H NMR (400 MHz,Chloroform-d) δ 7.80 - 7.63 (m, 2H), 7.31 (d, J = 8.0 Hz, 2H), 7.25 (dd, J = 8.6, 1.1 Hz, 2H), 6.90 (dd, J= 8.6, 1.2 Hz, 2H), 6.26 (d, J = 16.2 Hz, 1H), 6.15 (dd, J = 16.2, 1.1 Hz, 1H), 5.86 (ddd, J = 17.5, 10.7,1.1 Hz, 1H), 5.12 - 5.07 (m, 1H), 5.07 (m, 2H), 2.47 (d, J = 18.6 Hz, 3H), 1.93 (dd, J = 10.6, 6.3 Hz,2H), 1.67 (s, 3H), 1.58 (s, 3H), 1.54 - 1.44 (m, 2H), 1.19 (d, J = 1.2 Hz, 3H). 13C NMR (101 MHz,CDCl3) δ 148.38, 145.37, 145.24, 139.08, 136.84, 132.40, 131.42, 130.20, 129.69, 128.53, 127.03,125.85, 124.58, 122.38, 112.25, 42.67, 41.13, 25.66, 23.17, 23.16, 21.69, 17.62. HRMS (ESI-TOF)calculated for C25H30O3S ([M - H]+): 409.1838, found: 409.1827 (94% yield).

Reference： [1]Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 75 - 80]

32
[ 10309-37-2 ]
[ 100-39-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate In benzene at 20 - 80℃; for 36h; Inert atmosphere;	Etherification Reaction: compounds 10-13 General procedure: To a solution of Bakuchiol (1.0 mmol) in benzene (0.5M), K2CO3 (3.0 mmol) and methyl iodide orbenzyl bromide (4.0 mmol) were added at RT under an inert gas atmosphere. Then, the reaction wasstirred for 36hr under refluxing conditions (80°C). Then, the reaction mixture was filtered through celiteand washed with EtOAc (15 mL). The resulting mixture was quenched with 1N HCl (15 mL), washedwith saturated brine solution (25 mL) and H2O (15 mL). The mixture was extracted EtOAc (3 × 15 mL),the combined organic layer was dried over MgSO4 and filtered. The filtrate was concentrated in vacuoand purified by silica gel column chromatography (Hex/EtOAc, 49:1) to afford the desired compound.

Reference： [1]Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 75 - 80]

33
[ 699-08-1 ]
[ 17015-60-0 ]
C₂₆H₃₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 12h;Inert atmosphere; Microwave irradiation;	General procedure: To a solution of aryl iodide (1.5 mmol), bakuchiol (1.0 mmol) in DMF (10 mL), K2CO3 (2.0 mmol), and the Pd(PPh3)4 catalyst (5 mol%) were added under anhydrous conditions. The reaction mixture was degassed and placed on a microwave reactor, and heated to 140C for 12 hr. Then, the reaction mixture was cooled to RT and the precipitate filtered. The resultant mixture was washed with brine (35 mL) andH2O (4 × 30 mL). The organic layer was dried over anhydrous Na2SO4, evaporated under reduced pressure and the residue was purified by silica gel column chromatography (Hex/EtOAc, 9:1) to affordthe desired product.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 113,p. 75 - 80

34
[ 591-50-4 ]
[ 10309-37-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
71%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 12h; Inert atmosphere; Microwave irradiation;	General Procedure for Pd(0) mediated Heck Reaction: compounds 51-54 General procedure: To a solution of aryl iodide (1.5 mmol), bakuchiol (1.0 mmol) in DMF (10 mL), K2CO3 (2.0 mmol), and the Pd(PPh3)4 catalyst (5 mol%) were added under anhydrous conditions. The reaction mixture was degassed and placed on a microwave reactor, and heated to 140°C for 12 hr. Then, the reaction mixture was cooled to RT and the precipitate filtered. The resultant mixture was washed with brine (35 mL) andH2O (4 × 30 mL). The organic layer was dried over anhydrous Na2SO4, evaporated under reduced pressure and the residue was purified by silica gel column chromatography (Hex/EtOAc, 9:1) to affordthe desired product.

Reference： [1]Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 75 - 80]

35
[ 624-31-7 ]
[ 10309-37-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 12h; Inert atmosphere; Microwave irradiation;	General Procedure for Pd(0) mediated Heck Reaction: compounds 51-54 General procedure: To a solution of aryl iodide (1.5 mmol), bakuchiol (1.0 mmol) in DMF (10 mL), K2CO3 (2.0 mmol), and the Pd(PPh3)4 catalyst (5 mol%) were added under anhydrous conditions. The reaction mixture was degassed and placed on a microwave reactor, and heated to 140°C for 12 hr. Then, the reaction mixture was cooled to RT and the precipitate filtered. The resultant mixture was washed with brine (35 mL) andH2O (4 × 30 mL). The organic layer was dried over anhydrous Na2SO4, evaporated under reduced pressure and the residue was purified by silica gel column chromatography (Hex/EtOAc, 9:1) to affordthe desired product.

Reference： [1]Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 75 - 80]

36
[ 10309-37-2 ]
[ 1998064-19-9 ]

Yield	Reaction Conditions	Operation in experiment
16.4%	With sulfuric acid In water for 8h;	3.7. Synthesis of (S,E)-4-(7-hydroxy-3,7-dimethyl-3-vinyloct-1-en-1-yl)phenol (9) and (S,E)-4-(7-methoxy-3,7-dimethyl-3-vinyloct-1-en-1-yl)phenol (10) Compound 1 (0.5 mM, Rf = 0.70, DCM:methanol = 50:1) was dissolved in 5 mL methanol,and dilute sulphuric acid (1 mL, 3 M) was slowly added with ice bath cooling. Then the temperaturewas raised up to 45 C and the mixture was stirred for 8 h until the reaction was complete (monitoredby TLC). After the methanol was removed under reduced pressure, the solid residue was extractedwith 250 mL water and the same volume of DCM. Then the organic layer was washed with water,dried over anhydrous sodium sulfate overnight, and concentrated under reduced pressure. The residuewas then purified by column chromatography on silica gel, using DCM and methanol mixture (80:1)as eluent, to give compounds 9 and 10.(S,E)-4-(7-hydroxy-3,7-dimethyl-3-vinyloct-1-en-1-yl)phenol (9). The yield was 16.4%. Rf = 0.20 (DCM:methanol = 50:1). 1H-NMR (CDCl3) δ 7.26-7.24 (m, 1H, Ar-H), 7.24-7.23 (m, 1H, Ar-H), 7.10 (s, 1H),6.77-6.76 (m, 1H, Ar-H), 6.75-6.74 (m, 1H, Ar-H), 6.24 (d, J = 16.2 Hz, 1H, 1-ene-H), 6.05 (d, J = 16.2 Hz,1H, 2-ene-H), 5.87 (dd, J = 17.5, 10.7 Hz, 1H, 3-ethenyl-H), 5.02 (ddd, J = 18.9, 14.1, 1.3 Hz, 2H,3-ethenyl-H), 1.48-1.44 (m, 4H, -CH2-), 1.37-1.33 (m, 2H, -CH2-), 1.26 (s, 1H, Ar-OH), 1.20 (s, 6H,7-CH3 and 8-CH3), 1.19 (s, 3H, 3-CH3). 13C-NMR (CDCl3) δ 154.9, 146.0, 135.8, 127.4 (2C), 126.6, 116.0,115.4 (2C), 111.9, 71.4, 44.6, 42.6, 41.9, 29.3 (2C), 23.5, 19.3. ESI-MS: m/z, [M H]+ 273.2.(S,E)-4-(7-methoxy-3,7-dimethyl-3-vinyloct-1-en-1-yl)phenol (10). The yield was 20.0%. Rf = 0.40 (DCM:methanol = 50:1). 1H-NMR (CDCl3) δ 7.25-7.24 (m, 1H, Ar-H), 7.24-7.23 (m, 1H, Ar-H), 6.78-6.76(m, 1H, Ar-H), 6.76-6.75 (m, 1H, Ar-H), 6.24 (d, J = 16.2 Hz, 1H, 1-ene-H), 6.05 (d, J = 16.2 Hz, 1H,2-ene-H), 5.87 (dd, J = 17.5, 10.7 Hz, 1H, 3-ethenyl-H), 5.04-4.98 (m, 2H, 3-ethenyl-2H), 3.16 (s, 3H,-OCH3), 1.47-1.41 (m, 4H, -CH2-), 1.34-1.28 (m, 2H, -CH2-), 1.18 (s, 3H, 3-CH3), 1.13 (s, 6H, -CH3).13C-NMR (CDCl3) δ 155.0, 146.1, 135.8, 130.6, 127.4 (2C), 126.6, 115.4 (2C), 111.9, 75.0, 49.1, 42.6, 42.0,40.5, 25.0 (2C), 23.5, 18.8. Its HR-ESI-MS exhibited a pseudo molecular ion peak at m/z 289.2139 [M + H]+ consistent with the molecular formula C19H28O2.

Reference： [1]Wu, Cheng-Zhu; Liu, Da-Chuan; Guo, Xing; Dai, Yiqun; Ma, Tao; Li, Hong-Mei; Huo, Qiang [Molecules, 2018, vol. 23, # 3]

37
[ 10309-37-2 ]
[ 106-94-5 ]
[ 74921-92-9 ]

Yield	Reaction Conditions	Operation in experiment
52%	Stage #1: bakuchiol With potassium carbonate In acetone for 1h; Reflux; Stage #2: propyl bromide In acetone Reflux;	3.3. Synthesis of (S,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-propoxybenzene (2) A mixture of bakuchiol (1, 256 mg, 1 mmol) and potassium carbonate (276 mg, 2 mmol) in acetone(5 mL) was stirred at reflux temperature for 1 h. Then bromopropane (185 mg, 1.5 mmol) was added,and the mixture was refluxed for another 5 h approximately. After cooling to the room temperatureand removing the solution, the reaction was poured in some water and stirred for 0.5 h to washaway the remaining potassium carbonate. Then the solid was obtained by filtered and purified bysilica gel column chromatography with 50:1 n-hexane:ethyl acetate mixture to obtain compound 2.The yield was 52.0%. Rf = 0.85 (n-hexane: ethyl acetate = 10:1). 1H-NMR (CDCl3) δ 7.27 (d, J = 8.0 Hz,2H, Ar-H), 6.82 (d, J = 8.3 Hz, 2H, Ar-H), 6.25 (d, J = 15.9 Hz, 1H, 1-ene-H), 6.04 (d, J = 16.3 Hz, 1H,2-ene-H), 5.87 (dd, J = 17.4, 10.7 Hz, 1H, 3-ethenyl-H), 5.10 (t, J = 6.4 Hz, 1H, 6-ene-H), 5.05-4.95 (m,2H, 3-ethenyl-2H), 3.90 (t, J = 6.4 Hz, 2H, -OCH2-), 2.00-1.88 (m, 2H, -CH2-), 1.79 (dd, J = 13.9, 6.9 Hz,2H, -CH2-), 1.66 (s, 3H, -CH3), 1.57 (s, 3H, -CH3), 1.52-1.43 (m, 2H, -CH2-), 1.18 (s, 3H, 3-CH3), 1.02 (t,J = 7.2 Hz, 3H, -CH3). 13C-NMR (CDCl3) δ 158.3, 146.1, 135.7, 131.3, 130.5, 127.1 (2C), 126.6, 124.9,114.6 (2C), 111.8, 69.6, 42.5, 41.3, 25.7, 23.4, 23.3, 22.6, 17.6, 10.5. ESI-MS: m/z, [M + H]+ 299.2.

Reference： [1]Wu, Cheng-Zhu; Liu, Da-Chuan; Guo, Xing; Dai, Yiqun; Ma, Tao; Li, Hong-Mei; Huo, Qiang [Molecules, 2018, vol. 23, # 3]

38
[ 10309-37-2 ]
[ 123-62-6 ]
[ 1361320-38-8 ]

Yield	Reaction Conditions	Operation in experiment
61.5%	With dmap In dichloromethane at 20℃;	3.4. General Procedure for the Synthesis of (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl) Phenyl SubstitutedCarboxylic Esters 3-6 General procedure: Compounds 3-6 were synthesized from compound 1 with an appropriate alkanoic anhydrideor acyl chloride in the presence of a catalytic amount of N,N-dimethylaminopyridine with 5 mLdichloromethane (DCM) as solvent. Reactions were monitored by TLC. After the reaction wascomplete, the mixture was poured in ice water and the resulting oily material, which was waterinsoluble, was separated and dissolved in DCM. Then the organic layer was washed with water fortwice, then dried by anhydrous calcium chloride and concentrated under reduced pressure. The acylderivatives were purified by silica gel column chromatography with a 40:1 n-hexane:ethyl acetatemixture as eluent to give compounds 3-6. The yields, Rf (n-hexane:ethyl acetate = 10:1) and the spectraldata of compounds 3-6 are given below.

Reference： [1]Wu, Cheng-Zhu; Liu, Da-Chuan; Guo, Xing; Dai, Yiqun; Ma, Tao; Li, Hong-Mei; Huo, Qiang [Molecules, 2018, vol. 23, # 3]

39
[ 1002-69-3 ]
bakuchiol [ No CAS ]
[ 1361320-43-5 ]

Yield	Reaction Conditions	Operation in experiment
11.7%	With dmap In dichloromethane at 20℃;	3.4. General Procedure for the Synthesis of (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl) Phenyl SubstitutedCarboxylic Esters 3-6 General procedure: Compounds 3-6 were synthesized from compound 1 with an appropriate alkanoic anhydrideor acyl chloride in the presence of a catalytic amount of N,N-dimethylaminopyridine with 5 mLdichloromethane (DCM) as solvent. Reactions were monitored by TLC. After the reaction wascomplete, the mixture was poured in ice water and the resulting oily material, which was waterinsoluble, was separated and dissolved in DCM. Then the organic layer was washed with water fortwice, then dried by anhydrous calcium chloride and concentrated under reduced pressure. The acylderivatives were purified by silica gel column chromatography with a 40:1 n-hexane:ethyl acetatemixture as eluent to give compounds 3-6. The yields, Rf (n-hexane:ethyl acetate = 10:1) and the spectraldata of compounds 3-6 are given below.

Reference： [1]Wu, Cheng-Zhu; Liu, Da-Chuan; Guo, Xing; Dai, Yiqun; Ma, Tao; Li, Hong-Mei; Huo, Qiang [Molecules, 2018, vol. 23, # 3]

40
[ 10309-37-2 ]
[ 98-88-4 ]
[ 2043947-58-4 ]

Yield	Reaction Conditions	Operation in experiment
13.9%	With dmap In dichloromethane at 20℃;	3.4. General Procedure for the Synthesis of (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl) Phenyl SubstitutedCarboxylic Esters 3-6 General procedure: Compounds 3-6 were synthesized from compound 1 with an appropriate alkanoic anhydrideor acyl chloride in the presence of a catalytic amount of N,N-dimethylaminopyridine with 5 mLdichloromethane (DCM) as solvent. Reactions were monitored by TLC. After the reaction wascomplete, the mixture was poured in ice water and the resulting oily material, which was waterinsoluble, was separated and dissolved in DCM. Then the organic layer was washed with water fortwice, then dried by anhydrous calcium chloride and concentrated under reduced pressure. The acylderivatives were purified by silica gel column chromatography with a 40:1 n-hexane:ethyl acetatemixture as eluent to give compounds 3-6. The yields, Rf (n-hexane:ethyl acetate = 10:1) and the spectraldata of compounds 3-6 are given below.

Reference： [1]Wu, Cheng-Zhu; Liu, Da-Chuan; Guo, Xing; Dai, Yiqun; Ma, Tao; Li, Hong-Mei; Huo, Qiang [Molecules, 2018, vol. 23, # 3]

41
[ 67-56-1 ]
[ 10309-37-2 ]
[ 2043947-57-3 ]

Yield	Reaction Conditions	Operation in experiment
20%	With sulfuric acid In water for 8h;	3.7. Synthesis of (S,E)-4-(7-hydroxy-3,7-dimethyl-3-vinyloct-1-en-1-yl)phenol (9) and (S,E)-4-(7-methoxy-3,7-dimethyl-3-vinyloct-1-en-1-yl)phenol (10) Compound 1 (0.5 mM, Rf = 0.70, DCM:methanol = 50:1) was dissolved in 5 mL methanol,and dilute sulphuric acid (1 mL, 3 M) was slowly added with ice bath cooling. Then the temperaturewas raised up to 45 C and the mixture was stirred for 8 h until the reaction was complete (monitoredby TLC). After the methanol was removed under reduced pressure, the solid residue was extractedwith 250 mL water and the same volume of DCM. Then the organic layer was washed with water,dried over anhydrous sodium sulfate overnight, and concentrated under reduced pressure. The residuewas then purified by column chromatography on silica gel, using DCM and methanol mixture (80:1)as eluent, to give compounds 9 and 10.(S,E)-4-(7-hydroxy-3,7-dimethyl-3-vinyloct-1-en-1-yl)phenol (9). The yield was 16.4%. Rf = 0.20 (DCM:methanol = 50:1). 1H-NMR (CDCl3) δ 7.26-7.24 (m, 1H, Ar-H), 7.24-7.23 (m, 1H, Ar-H), 7.10 (s, 1H),6.77-6.76 (m, 1H, Ar-H), 6.75-6.74 (m, 1H, Ar-H), 6.24 (d, J = 16.2 Hz, 1H, 1-ene-H), 6.05 (d, J = 16.2 Hz,1H, 2-ene-H), 5.87 (dd, J = 17.5, 10.7 Hz, 1H, 3-ethenyl-H), 5.02 (ddd, J = 18.9, 14.1, 1.3 Hz, 2H,3-ethenyl-H), 1.48-1.44 (m, 4H, -CH2-), 1.37-1.33 (m, 2H, -CH2-), 1.26 (s, 1H, Ar-OH), 1.20 (s, 6H,7-CH3 and 8-CH3), 1.19 (s, 3H, 3-CH3). 13C-NMR (CDCl3) δ 154.9, 146.0, 135.8, 127.4 (2C), 126.6, 116.0,115.4 (2C), 111.9, 71.4, 44.6, 42.6, 41.9, 29.3 (2C), 23.5, 19.3. ESI-MS: m/z, [M H]+ 273.2.(S,E)-4-(7-methoxy-3,7-dimethyl-3-vinyloct-1-en-1-yl)phenol (10). The yield was 20.0%. Rf = 0.40 (DCM:methanol = 50:1). 1H-NMR (CDCl3) δ 7.25-7.24 (m, 1H, Ar-H), 7.24-7.23 (m, 1H, Ar-H), 6.78-6.76(m, 1H, Ar-H), 6.76-6.75 (m, 1H, Ar-H), 6.24 (d, J = 16.2 Hz, 1H, 1-ene-H), 6.05 (d, J = 16.2 Hz, 1H,2-ene-H), 5.87 (dd, J = 17.5, 10.7 Hz, 1H, 3-ethenyl-H), 5.04-4.98 (m, 2H, 3-ethenyl-2H), 3.16 (s, 3H,-OCH3), 1.47-1.41 (m, 4H, -CH2-), 1.34-1.28 (m, 2H, -CH2-), 1.18 (s, 3H, 3-CH3), 1.13 (s, 6H, -CH3).13C-NMR (CDCl3) δ 155.0, 146.1, 135.8, 130.6, 127.4 (2C), 126.6, 115.4 (2C), 111.9, 75.0, 49.1, 42.6, 42.0,40.5, 25.0 (2C), 23.5, 18.8. Its HR-ESI-MS exhibited a pseudo molecular ion peak at m/z 289.2139 [M + H]+ consistent with the molecular formula C19H28O2.

Reference： [1]Wu, Cheng-Zhu; Liu, Da-Chuan; Guo, Xing; Dai, Yiqun; Ma, Tao; Li, Hong-Mei; Huo, Qiang [Molecules, 2018, vol. 23, # 3]

42
[ 10309-37-2 ]
[ 168400-04-2 ]
[ 168400-03-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 42% 2: 14%	With hydrogenchloride In dichloromethane; water at 20℃; Overall yield = 56 percent; Optical yield = 50 percent de;	Preparation of cyclobakuchiols A-D For the synthesis of 2 and 3 started, conc. HCl (0.4 mL) was added to a solution of 1 (101.5mg, 0.396 mmol) in CH2Cl2/H2O (20/1, 2 mL) at room temperature. The mixture was stirredovernight, quenched with saturated NaHCO3 (2 mL) and extracted with CH2Cl2 (3 × 10 mL)before drying over anhydrous MgSO4, filtering, and concentrating. The crude mixture waspurified by silica gel column chromatography (SiO2 = 3 g, hexane/ethyl acetate = 10/1) toobtain a diastereomeric mixture of 2, 3 (57.1 mg, 56%, 2: 3 = 75: 25), and 4 (3.1 mg, 3%) (Fig1A). Furthermore, a part of the diastereomeric mixture of 2 and 3 was separated by HPLC toafford 2 (RT: 9.08 min) and 3 (RT: 11.22 min), respectively. Data for 2: [α]D21-8.0° (c 0.1,CHCl3); IR (neat) 3332, 1642, 1605, 1509, 1447, 1369 cm-1; HRMS (EI) m/z calc for C18H24O,256.1827 [M+]; found 256.1833; 1H NMR (400 MHz, CDCl3) δ 0.98 (s, 3H, 10-CH3), 1.34-1.45(m, 2H, 2-CH2(a), 5-CH2(a)), 1.48 (s, 3H, 9-CH3), 1.53-1.70 (m, 2H, 2-CH2(b), 5-CH2(b)),1.78-1.84 (m, 2H, 6-CH2), 2.21 (dt, J = 4.0, 11.6 Hz, 1H, 4-CH), 2.66 (dt, J = 3.6, 11.6 Hz, 1H,3-CH), 4.51, (brs, 1H, 8-CH2(a)), 4.53 (brs, 1H, 8-CH2(b)), 4.60 (brs, 1H, OH), 5.07 (dd,J = 1.2, 18.0 Hz, 1H, 12-CH2(a)), 5.13 (dd, J = 1.6, 10.8 Hz, 1H, 12-CH2(b)), 5.85 (dd, J = 11.2,17.6 Hz, 1H, 11-CH), 6.72 (d, J = 8.8 Hz, 2H, 3’,5’-CH), 6.99 (d, J = 8.8 Hz, 2H, 2’,6’-CH); 13CNMR (100 MHz, CDCl3) δ 19.7 (C9), 29.0 (C5), 31.6 (C10), 37.6 (C1), 37.8 (C6), 42.8 (C3),47.5 (C2), 51.5 (C4), 111.2 (C8), 112.6 (C12), 115.0 (C3’,5’), 128.5 (C2’,6’), 138.3 (C1’), 146.3(C11), 148.6 (C7), 153.4 (C4’). Data for 3: [α]D21-34.8° (c 0.05, CHCl3); IR (neat) 3338, 2959,2925, 1644, 1512, 1450, 1372 cm-1; HRMS (EI) m/z calc for C18H24O, 256.1827 [M+]; found256.1828; 1H NMR (400 MHz, CDCl3) δ 1.14 (s, 3H, 10-CH3), 1.45-1.77 (m, 6H, 2,5,6-CH2),1.53 (s, 3H, 9-CH3), 2.19 (dt, J = 4.4, 11.6 Hz, 1H, 4-CH), 2.72 (dt, J = 3.6, 12.0 Hz, 1H, 3-CH),4.54, (brs, 1H, OH), 4.55 (brs, 1H, 12-CH2(a)), 4.57 (brs, 1H, 12-CH2(b)), 4.86 (dd, J = 4.0,10.8 Hz, 1H, 8-CH2(a)), 4.93 (dd, J = 4.1, 17.6 Hz, 1H, 8-CH2(b)), 5.81 (dd, J = 10.8, 17.6 Hz,1H, 11-CH), 6.72 (d, J = 8.4 Hz, 2H, 3’,5’-CH), 7.01 (d, J = 8.4 Hz, 2H, 2’,6’-CH); 13C NMR(100 MHz, CDCl3) δ 19.8 (C9), 22.2 (C10), 28.3 (C5), 36.6 (C6), 37.0 (C1), 42.3 (C3), 46.5(C2), 51.6 (C4), 109.2 (C12), 111.3 (C8), 115.0 (C3’,5’), 128.7 (C2’,6’), 138.1 (C1’), 148.5 (C7),150.7 (C11), 153.5 (C4’).

Reference： [1]Shoji, Masaki; Esumi, Tomoyuki; Tanaka, Narue; Takeuchi, Misa; Yamaji, Saki; Watanabe, Mihiro; Takahashi, Etsuhisa; Kido, Hiroshi; Yamamoto, Masayuki; Kuzuhara, Takashi [PLoS ONE, 2021, vol. 16, # 3 March]

43
[ 10309-37-2 ]
[ 109-64-8 ]
[ 2640518-84-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate In propan-2-one for 6h; Reflux;
80%	With potassium carbonate In propan-2-one for 6h; Reflux;	Preparation of compound 1 bakuchiol (162 mg, 0.632 mmol) was dissolved in acetone (10 mL), and then potassium carbonate (436.6 mg, 3.16 mmol) and 1,3-dibromopropane (480.8 μL, 4.74 mmol) were added, and the mixture was refluxed and stirred for 6 hours. After the reaction is completed, the reaction mixture is diluted with ethyl acetate and extracted twice with water. The organic phase is concentrated under reduced pressure. The crude product was purified by silica gel chromatography (petroleum ether/ethyl acetate, 8:1, v/v) to give Compound 1 a colorless transparent oil (190.2 mg, 80%).

Reference： [1]Li, Hongxia; Liu, Jiayong; Liu, Chuan-Fa; Li, Haizhou; Luo, Jiachun; Fang, Shanfang; Chen, Yongzhi; Zhong, Rongcui; Liu, Shouping; Lin, Shuimu [Journal of Medicinal Chemistry, 2021, vol. 64, # 9, p. 5603 - 5619]
[2]Current Patent Assignee: JIANGXI SHIMEI PHARMACEUTICAL - WO2022/88091, 2022, A1 Location in patent: Page/Page column 18-19

44
[ 10309-37-2 ]
[ 471-25-0 ]
[ 2757911-20-7 ]

Yield	Reaction Conditions	Operation in experiment
83.4%	With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 25℃;

Reference： [1]Bai, Chunmei; Bian, Ming; Du, Huan-Huan; Gong, Guohua; Liu, Chunyan; Ma, Qianqian; Quan, Zhe-Shan; Wei, Chengxi [Journal of Natural Products, 2022, vol. 85, # 1, p. 15 - 24]

45
[ 1477-50-5 ]
[ 10309-37-2 ]
[ 2757911-09-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 25℃;

Reference： [1]Bai, Chunmei; Bian, Ming; Du, Huan-Huan; Gong, Guohua; Liu, Chunyan; Ma, Qianqian; Quan, Zhe-Shan; Wei, Chengxi [Journal of Natural Products, 2022, vol. 85, # 1, p. 15 - 24]

46
[ 10517-21-2 ]
[ 10309-37-2 ]
[ 2757911-10-5 ]

Yield	Reaction Conditions	Operation in experiment
69.2%	With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 25℃;

Reference： [1]Bai, Chunmei; Bian, Ming; Du, Huan-Huan; Gong, Guohua; Liu, Chunyan; Ma, Qianqian; Quan, Zhe-Shan; Wei, Chengxi [Journal of Natural Products, 2022, vol. 85, # 1, p. 15 - 24]

47
[ 4382-54-1 ]
[ 10309-37-2 ]
[ 2757911-11-6 ]

Yield	Reaction Conditions	Operation in experiment
67.1%	With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 25℃;

Reference： [1]Bai, Chunmei; Bian, Ming; Du, Huan-Huan; Gong, Guohua; Liu, Chunyan; Ma, Qianqian; Quan, Zhe-Shan; Wei, Chengxi [Journal of Natural Products, 2022, vol. 85, # 1, p. 15 - 24]

48
[ 10349-57-2 ]
[ 10309-37-2 ]
[ 2757911-12-7 ]

Yield	Reaction Conditions	Operation in experiment
82.2%	With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 25℃;

Reference： [1]Bai, Chunmei; Bian, Ming; Du, Huan-Huan; Gong, Guohua; Liu, Chunyan; Ma, Qianqian; Quan, Zhe-Shan; Wei, Chengxi [Journal of Natural Products, 2022, vol. 85, # 1, p. 15 - 24]

49
[ 10309-37-2 ]
[ 621-82-9 ]
[ 2757911-13-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 25℃;

Reference： [1]Bai, Chunmei; Bian, Ming; Du, Huan-Huan; Gong, Guohua; Liu, Chunyan; Ma, Qianqian; Quan, Zhe-Shan; Wei, Chengxi [Journal of Natural Products, 2022, vol. 85, # 1, p. 15 - 24]

50
[ 10309-37-2 ]
[ 105-36-2 ]
[ 2760720-17-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate In propan-2-one for 3h; Reflux;	Preparation of compound 36 bakuchiol (93.5 mg, 0.357 mmol) was dissolved in acetone (10 mL), followed by potassium carbonate (123.5 mg, 0.893 mmol) and ethyl bromoacetate (81 μL, 0.081 mmol). The reaction mixture was refluxed and stirred for 3h. After the reaction is completed, the resulting mixture is diluted with ethyl acetate and extracted twice with water. The organic phase is concentrated under reduced pressure. The crude product was purified by silica gel chromatography (petroleum ether / ethyl acetate, 6:1, v / v) to give compound 36 as a pale yellow oil (114.1 mg, 93%).

Reference： [1]Current Patent Assignee: JIANGXI SHIMEI PHARMACEUTICAL - WO2022/88091, 2022, A1 Location in patent: Page/Page column 26

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. :	10309-37-2	MDL No. :
Formula :	C₁₈H₂₄O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LFYJSSARVMHQJB-QIXNEVBVSA-N
M.W :	256.38	Pubchem ID :	5468522
Synonyms :	(S)-(+)-Bakuchiol	Chemical Name :	(S,E)-4-(3,7-Dimethyl-3-vinylocta-1,6-dien-1-yl)phenol

Num. heavy atoms :	19
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	6
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	85.42
TPSA :	20.23 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.52 cm/s

Log Po/w (iLOGP) :	3.54
Log Po/w (XLOGP3) :	6.12
Log Po/w (WLOGP) :	5.24
Log Po/w (MLOGP) :	4.59
Log Po/w (SILICOS-IT) :	5.1
Consensus Log Po/w :	4.92

[ CAS No. 10309-37-2 ] {[proInfo.proName]}

Quality Control of [ 10309-37-2 ]

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Product Details of [ 10309-37-2 ]

Calculated chemistry of [ 10309-37-2 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 10309-37-2 ]

Application In Synthesis of [ 10309-37-2 ]

[ 10309-37-2 ] Synthesis Path-Downstream 1~50

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Log S (ESOL) :	-5.12
Solubility :	0.00193 mg/ml ; 0.00000754 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.33
Solubility :	0.000121 mg/ml ; 0.000000471 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-4.47
Solubility :	0.00865 mg/ml ; 0.0000337 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.13

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	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