[ CAS No. 107-86-8 ] {[proInfo.proName]}

Name: 107-86-8|3-Methylbut-2-enal|97%
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Quality Control of [ 107-86-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 107-86-8 ]

Product Details of [ 107-86-8 ]

CAS No. :	107-86-8	MDL No. :	MFCD00010291
Formula :	C₅H₈O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SEPQTYODOKLVSB-UHFFFAOYSA-N
M.W :	84.12	Pubchem ID :	61020
Synonyms :

Calculated chemistry of [ 107-86-8 ]

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.4
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	25.87
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.48
Log Po/w (XLOGP3) :	1.17
Log Po/w (WLOGP) :	1.15
Log Po/w (MLOGP) :	0.9
Log Po/w (SILICOS-IT) :	0.83
Consensus Log Po/w :	1.11

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.03
Solubility :	7.8 mg/ml ; 0.0928 mol/l
Class :	Very soluble
Log S (Ali) :	-1.12
Solubility :	6.33 mg/ml ; 0.0752 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.58
Solubility :	22.0 mg/ml ; 0.261 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.55

Safety of [ 107-86-8 ]

Signal Word:	Danger	Class:	8,3
Precautionary Statements:	P210-P233-P240-P241-P242-P243-P261-P264-P270-P271-P272-P273-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P312-P333+P313-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501	UN#:	2920
Hazard Statements:	H226-H302-H313-H314-H317-H331-H402	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 107-86-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 107-86-8 ]
Downstream synthetic route of [ 107-86-8 ]

[ 107-86-8 ] Synthesis Path-Upstream 1~4

1
[ 107-86-8 ]
[ 55876-82-9 ]

Reference： [1] Journal of Chemical Research, Miniprint, 1985, # 8, p. 2801 - 2817

2
[ 107-86-8 ]
[ 95-01-2 ]
[ 54287-99-9 ]

Yield	Reaction Conditions	Operation in experiment
50%	With calcium hydroxide In methanol at 20℃; for 48 h;	2,4-Dihydroxybenzaldehyde (15) (3 g/20.17 mmol), calcium hydroxide (1.543 g/20.8 mmol) and 150 mL of methanol were place in a two-necked round-bottom flask. Then, prenal (9.135 g/108.6 mmol) was added dropwise. The mixture was allowed to stir at room temperature for 48 h. The reaction was quenched with HCl 1 M until pH 1–2. The methanol was evaporated and the aqueous phase was extracted with 3 × 150 mL of ethyl acetate. The organic phase was washed with 2 × 100 mL of brine, dried over sodium sulfate anhydrous, filtered and the organic solvent evaporated. The crude product was purified by silica gel flash chromatography (n-hexane/ethyl acetate 9:1). Compound 16 was crystallized from n-hexane/ethyl acetate 3:1 as a yellow solid (2.06 g/50percent).
50%	With calcium hydroxide In methanol at 20℃; for 48 h;	2,4-Dihydroxybenzaldehyde (42) (3g/20.17mmol), calcium hydroxide (1.543g/20.8mmol) and 150mL of methanol were placed in a round-bottom flask. Then, prenal (9.135g/108.6mmol) was added dropwise. The mixture was stirred at room temperature for 48h. The reaction was quenched with HCl 1M until pH 1–2. The methanol was evaporated and the aqueous phase was extracted with 3×150mL of ethyl acetate. The organic phase was washed with 2×100mL of brine, dried over sodium sulfate anhydrous, filtered and the organic solvent evaporated. The crude product was purified by silica gel flash chromatography (n-hexane/ethyl acetate 9:1). Compound 43 was crystallized from n-hexane/ethyl acetate 3:1 as a yellow solid (2.06g/50percent).6-Formyl-5-hydroxy-2,2-dimethyl-2H-benzopyran (43). Mp: 68–69°C. IR ν_max (cm⁻¹) (KBr): 3464, 2967, 2922, 2857, 1628, 1484, 1330, 1294, 1247, 1176, 1107, 1081, 748. ¹H NMR (300.13MHz, CDCl₃) δ (ppm): 11.65 (OH), 9.66 (s, CHO), 7.29 (d, J=8.6), 6.88 (d, J=10.0), 6.44 (d, J=8.6), 5.61 (d, J=10.0), 1.46 (s, 6H). ¹³C NMR (100.63MHz, CDCl₃) δ (ppm): 194.5, 160.6, 158.7, 134.7, 128.6, 115.2, 115.1, 109.4, 108.8, 78.2, 28.4. EIMS m/z (percent): 205 (5, [M+1]^+.), 204 (10 [M]^+.), 190 (15), 189 (100), 187 (60), 159 (12), 131 (12), 103 (10), 77 (12), 51 (6). HRMS (ESI) m/z calcd for C₁₂H₁₃O₃ [M+H]⁺: 205.08570, found: 205.08592.
0.68 g	With calcium hydroxide In methanol at 20℃; for 12 h;	A 1 g portion of 2,4-2 hydroxybenzaldehyde (Compound 2 shown in Figure 1)0.514 g Ca (OH) 2, methanol150mL.3.045 g of prenyl aldehyde (compound 1 shown in FIG. 1) was then added dropwise.Stir at room temperature for 12h.Quench with HCl (1 M) until the pH is 1-2.Methanol was evaporated and the aqueous phase was extracted with 3 * 150 mL of ethyl acetate.The organic phase was washed with 2 * 100 mL saturated brine, dried over anhydrous Na2SO4,Vacuum filtration, and spin dry. The crude product was passed through a column of silica gel (petroleum ether: ethyl acetate = 9: 1)Crystallization gave product 3 (0.68 g) as shown in FIG.

Reference： [1] Journal of Medicinal Chemistry, 2018,
[2] Journal of Organic Chemistry, 2015, vol. 80, # 22, p. 11460 - 11467
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 32, p. 8092 - 8096
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 2941 - 2959
[5] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 798 - 816
[6] Tetrahedron, 2001, vol. 57, # 25, p. 5335 - 5338
[7] Tetrahedron Letters, 2009, vol. 50, # 36, p. 5075 - 5079
[8] Advanced Synthesis and Catalysis, 2005, vol. 347, # 4, p. 555 - 562
[9] Patent: CN106187974, 2016, A, . Location in patent: Paragraph 0044

3
[ 107-86-8 ]
[ 95-01-2 ]
[ 54287-99-9 ]
[ 33279-69-5 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1999, vol. 72, # 2, p. 259 - 263

4
[ 107-86-8 ]
[ 33143-29-2 ]

Reference： [1] Journal of Molecular Catalysis A: Chemical, 2015, vol. 398, p. 11 - 16
[2] Tetrahedron, 2016, vol. 72, # 51, p. 8406 - 8416

[ 107-86-8 ] Synthesis Path-Downstream 1~88

1
[ 107-86-8 ]
[ 3917-41-7 ]
[ 116-31-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	In water at 20℃; for 0.0833333h;	13 Step 13 1) To a solution of 0.31 g of 3-methyl-2-butenal in 8 mL of water, quickly add 0.12 g of β-C15 aldehyde and stir at room temperature. 2) After 5 minutes, filter the resulting solid and dry it. 0.39 g (yield 95%) of all trans retinal was obtained. This stage is characterized by Knoevenagel condensation and all trans retinal formation.
	With piperidine; ethanol; acetic acid at 15 - 20℃;

Reference： [1]Current Patent Assignee: ARCAEIR - KR2021/51646, 2021, A Location in patent: Page/Page column 0029; 0094-0097
[2]Arens; van Dorp [Recueil des Travaux Chimiques des Pays-Bas, 1948, vol. 67, p. 973,976] Kuhn; Morris [Chemische Berichte, 1937, vol. 70, p. 853,857] Karrer; Rueegger [Helvetica Chimica Acta, 1940, vol. 23, p. 284] Heilbron; Weedon [Bulletin de la Societe Chimique de France, 1958, p. 83,87, 90]

2
[ 52851-41-9 ]
[ 107-86-8 ]
[ 523-64-8 ]

Reference： [1]Tetrahedron Letters,1975,p. 3407 - 3410

3
[ 3017-70-7 ]
[ 107-86-8 ]
2,3,6-trimethyl-hepta-2,5-dien-4-ol [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1972,vol. 50,p. 2806 - 2816

4
[ 107-86-8 ]
[ 122-51-0 ]
[ 1740-74-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With Mo₁₁O₄₀PV*4H⁽¹⁺⁾ In ethanol at 20℃; for 1h; Green chemistry;	2.4.2. General procedure for the synthesis of1,1-diethoxy-3-methyl-2-butene PMo11V was used as catalyst in this preparation. Triethyl orthoformate (18 mmol), 3-methyl-2-butenal (18 mmol), and the catalyst (PMo11V, 1 mmol %) were added to absolute ethanol (5 mL) at 20 °C. The progress of the reaction was monitored by thin layer chromatography (TLC) and gas chromatography (GC) analyses. After stirring for 1 h, the excess of ethanol was removed by evaporation, and the resulting mixture was treated with toluene (10 mL); finally, the catalyst was recovered by centrifugation and washing with toluene (5 mL). The organic phase was dried on anhydrous Na2SO4, filtered and concentrated to obtain the crude acetal. The acetal was isolated as a clear, colorless liquid by vacuum distillation (89% yield, 116-119 °C at 170 mm Hg, and 117.0-118.5 °C at 171-172 mm Hg).
86%	With potassium hydrogensulfate In ethanol for 1h;
86.4%	In ethanol	1 Production of 1-1-diethoxy-3-methyl-2-butene Production of 1-1-diethoxy-3-methyl-2-butene 1.25 g undried catalyst KP-10 (Sud-Chemie) and 189.25 g triethyl orthoformate were placed in a flask in a nitrogen atmosphere in 225 ml absolute ethanol. While cooling 110.5 g 3-methyl-crotonaldehyde was added in drops over 30 minutes at 5° C. Cooling was then stopped, the reaction mixture was heated slowly to 20° C. and stirred for a total of 3.5 hours after the addition of 3-methyl-crotonaldehyde. The course of the reaction was monitored by gas cromatography. The catalyst was then filtered-off through a suction filter and washed with 20 ml ethanol, 2.6 g potassium carbonate was added to the filtrate and the ethanol was distilled off under vacuum (230 mbar/50° C./0.5 hour and 182 mbar/52° C./1 hour). After the potassium carbonate had been filtered off and washed with 20 ml ethanol, the product was distilled at 187 mbar/114° C. The 1,1-diethoxy-3-methyl-2-butene distillate obtained (143.4 g, 86.4% yield) had a content of 97.1% (boiling point: 114° C. at 187 mbar).

85%	With potassium hydrogen sulphate; potassium carbonate In ethanol	1.A A. A. 1,1-Diethoxy-3-methyl-2-butene Under an argon atmosphere, a 250-mL, round-bottomed flask equipped with a stir bar was charged with abs. ethanol (52 mL, 892 mmol, 5.0 eq). The flask was cooled to 4° C. (internal) in an ice bath. Triethyl orthoformate (29.7 mL, 178 mmol, 1.0 eq) was added followed by 3-methyl-2-butenal (17.2 mL, 178 mmol, 1.0 eq). The resulting clear, colorless solution was further cooled to 2° C. (internal). Potassium hydrogen sulfate (1.277 g, 9.38 mmol, 0.05 eq) was then added in one portion, resulting in an immediate exotherm to 10° C. The heterogeneous mixture was allowed to warm to 21° C. (internal) over 45 minutes (within 20 minutes, the mixture became slightly cloudy) and then stirred for an additional 15 minutes. The reaction mixture was then filtered and the remaining solid rinsed with abs. ethanol (5 mL). To the resulting clear, colorless solution was added anhydrous potassium carbonate (2.615 g, 18.92 mmol). The mixture was stirred for one hour before filtering off the potassium carbonate. The solid was rinsed with abs. ethanol (5 mL) and the filtrate was vacuum distilled (172 mm Hg) through a Vigereux column (13.5 cm) to produce 24.14 g (85% yield) of the title compound (boiling point 115°-119° C.).
51%	With ammonium nitrate In ethanol for 8h; Ambient temperature;
	With phosphoric acid In ethanol
	In ethanol Ambient temperature;
	With ammonium nitrate In ethanol at 20℃; for 24h;	4.2. 1,1-Diethoxy-3-methyl-2-butene 17 3-Methylbut-2-enal (1.00 g, 11.90 mmol) and triethyl orthoformate(2.0 mL, 11.90 mmol) were dissolved in EtOH (20 mL) atroom temperature. The mixture was stirred for 5 min and NH4NO3(0.24 g, 2.97 mmol, 25 mol%) added. The mixture was stirred for24 h. Saturated aqueous NaHCO3 (20 mL) and brine (10 mL) wereadded. The mixture was extracted using Et2O (3 20 mL), theorganic layers were combined, dried and filtered, and the solventswere removed under reduced pressure to give the title compound17 as a brown liquid, which was used without further purification.nmax (film)/cm1 2975, 2930, 2914, 2879, 1682, 1447, 1377, 1358, 1348, 1206, 1142, 1115, 1083, 1053, 1017, 991. 1H NMR (500 MHz,CDCl3): d 1.23 (m, 6H),1.72 (d, 3H, J 1.0 Hz),1.75 (d, 3H, J 1.0 Hz),3.42e3.58 (m, 2H), 3.60e3.63 (m, 2H), 5.14 (d, 1H, J 6.5 Hz), 5.30(d, 1H, J 6.5 Hz); 13C NMR (125 MHz, CDCl3): d 15.5, 18.4, 25.6,60.4, 98.6, 125.1, 137.6.
	With potassium hydrogensulfate In ethanol at 0℃; for 0.5h;	2.1 (1) at 0 ° C,Slowly add to the stirred ethanol (24mL)3-methyl-2-butenal (7.72 mL, 80 mmol), potassium hydrogen sulfate (0.545 g, 4 mmol) and triethyl orthoformate (13.3 mL, 80 mmol).Then, the reaction was carried out at 0 ° C for 30 minutes, and then the reaction was stirred at room temperature for 30 minutes.The resulting reaction solution was filtered and washed with 5 mL of ethanol to filtratePotassium carbonate was added thereto and the reaction was stirred at room temperature for 2 hours.After that, the reaction liquid was filtered, and the obtained filtrate was concentrated under reduced pressure at 35 ° C.The crude intermediate 5 was obtained and used directly in the next step.
	With potassium hydrogensulfate In ethanol at 0 - 20℃; for 1h;	4.1.4 3-Iodo-8,8-dimethylpyrano[2,3-f]chromen-4(8H)-one (7) 3-Methylbut-2-enal (7.72mL, 80mmol), KHSO4 (0.545g, 4mmol), and (EtO)3CH (13.3mL, 80mmol) were successively added to EtOH (24mL) at 0°C, keep stirring for 30min, and then stirred for another 30min at room temperature. The resulting mixture was filtered and washed with EtOH (5mL). K2CO3 (1.106g, 8mmol) was added and stirred for 2h at room temperature. Then, the resulting mixture was filtered and concentrated in vacuo to provide 6 as a colorless liquid. The crude 6 was used in next step without further purification.

Reference： [1]Romanelli, Gustavo; Sathicq, Ángel; Vázquez, Patricia; Villa, Aída; Alarcón, Edwin; Grajales, Edwing; Cubillos, Jairo [Journal of Molecular Catalysis A: Chemical, 2015, vol. 398, p. 11 - 16]
[2]North, Jeffrey T.; Kronenthal, David R.; Pullockaran, Annie J.; Real, Sharon D.; Chen, Helen Y. [Journal of Organic Chemistry, 1995, vol. 60, # 11, p. 3397 - 3400]
[3]Current Patent Assignee: LONZA GROUP AG; GLAXOSMITHKLINE PLC - US5919953, 1999, A
[4]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US5502220, 1996, A
[5]Hoepfner, Wolfgang; Weyerstahl, Peter [Liebigs Annalen der Chemie, 1986, # 1, p. 99 - 113]
[6]Julia,M. et al. [Bulletin de la Societe Chimique de France, 1965, p. 1007 - 1014]
[7]Mori, Atsunori; Arai, Isao; Yamamoto, Hisashi; Nakai, Hisao; Arai, Yoshinobu [Tetrahedron, 1986, vol. 42, # 23, p. 6447 - 6458]
[8]Bulman Page, Philip C.; Chan, Yohan; Noor Armylisas, Abu Hassan; Alahmdi, Mohammed [Tetrahedron, 2016, vol. 72, # 51, p. 8406 - 8416]
[9]Current Patent Assignee: SICHUAN UNIVERSITY - CN109810115, 2019, A Location in patent: Paragraph 0054; 0055; 0057
[10]Wu, Chuanhai; Tu, Yan-bei; Li, Ziyuan; Li, Yan-fang [Bioorganic Chemistry, 2019, vol. 88]

5
[ 13472-60-1 ]
[ 107-86-8 ]
[ 118066-95-8 ]

Yield	Reaction Conditions	Operation in experiment
95%		Preparation 46-Bromo-2,2-dimethyl-2H-pyrano[2,3-b]pyridin-4(3H)-one[00153]A solution of <strong>[13472-60-1]3,5-dibromo-2-methoxypyridine</strong> (1 1 .4 g, 42.7 mmol) in dry diethyl ether is cooled to -65 C and treated with BuLi (19 mL 2.5 M solution in hexane, 47.5 mmol) under argon atmosphere. The mixture is stirred at -70 C for 0.5 h. A solution of 3-methylbut-2-enal (3.44 g, 40.9 mmol) in dry THF (10 mL) is added to the mixture, and stirring is continued for another 0.5 h at -70 C. The reaction mixture is then warmed to r.t. and quenched with a saturated solution of sodium bicarbonate (100 mL). After extraction with DCM (3 x 100 mL) the combined organic layers are dried over Na2S04 and concentrated under reduced pressure to yield 1 -(5-bromo-2-methoxypyridin-3-yl)-3- methylbut-2-en-1 -ol (1 1 g, 95%).
95%		Example 7 (rac)-6-((4-Methoxy-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-yl)ethynyl)pyridin-2-amine A solution of <strong>[13472-60-1]3,5-dibromo-2-methoxypyridine</strong> (11.4 g, 42.7 mmol) in dry diethyl ether is cooled to -65 C and treated with BuLi (19 mL 2.5 M solution in hexane, 47.5 mmol) under argon atmosphere. The mixture is stirred at -70 C for 0.5 h. A solution of 3-methylbut-2-enal (3.44 g, 40.9 mmol) in dry THF (10 mL) is added to the mixture, and stirring is continued for another 0.5 h at -70 C. Then the reaction mixture is warmed to rt and quenched with a saturated solution of sodium bicarbonate (100 mL). After extraction with DCM (3x100 mL) the combined organic layers are dried over Na2SO4 and concentrated under reduced pressure to yield the intermediate 1-(5-bromo-2-methoxypyridin-3-yl)-3-methylbut-2-en-1-ol (11 g, 95%).

Reference： [1]Patent: WO2012/52451,2012,A1 .Location in patent: Page/Page column 50
[2]Patent: EP2650284,2013,A1 .Location in patent: Paragraph 0222
[3]Synthetic Communications,1988,vol. 18,p. 1111 - 1118

6
[ 7224-68-2 ]
[ 107-86-8 ]
[ 52617-31-9 ]

Reference： [1]Phytochemistry,1990,vol. 29,p. 1303 - 1306

7
[ 7224-68-2 ]
[ 107-86-8 ]
[ 35989-00-5 ]

Reference： [1]Journal of Chemical Research, Miniprint,1997,p. 1201 - 1215
[2]Phytochemistry,1990,vol. 29,p. 1303 - 1306

8
[ 24621-61-2 ]
[ 107-86-8 ]
(+)-(2R,4S)-4-Methyl-2-2'-methylprop-1'-enyl-1,3-dioxane [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1980,vol. 63,p. 1598 - 1603

9
[ 6290-03-5 ]
[ 107-86-8 ]
(-)-(2S,4R)-4-methyl-2-2'-methylprop-1'-enyl-1,3-dioxane [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1980,vol. 63,p. 1598 - 1603

10
[ 107-86-8 ]
[ 90-15-3 ]
[ 20213-32-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With phenylboronic acid In acetic acid; toluene for 4h; Heating;
93%	With benzoic acid; 3,5-bis-trifluromethylphenylboronic acid In n-heptane at 60℃; for 17h; Sealed tube;
86%	With picoline at 125℃; for 8h;

75%	In chloroform for 10h; Heating;
61%	With 1,2-diamino-benzene In dichloromethane at 40℃; for 72h; Inert atmosphere; Molecular sieve;	4. General Procedure for the Synthesis of 2H-Benzo[h]Chromene 3 General procedure: Dry CH2Cl2 (1.0 mL) was added to a mixture of o-phenylenediamine (IX, 0.04 mmol),enal 1 (0.30 mmol) and arylol 2 (0.20 mmol) under Ar. The reaction was stirred at 40 Cuntil the completion of 2 monitored by TLC. Then, the mixture was applied to columnchromatography directly and eluted with ethyl ether and hexane (9/1) to give product 3.

Reference： [1]Alves, Glaucia B. C.; Lopes, Rosangela S. C.; Lopes, Claudio C.; Snieckus, Victor [Synthesis, 1999, # 11, p. 1875 - 1877]
[2]Dimakos, Victoria; Singh, Tishaan; Taylor, Mark S. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 28, p. 6703 - 6711]
[3]Lamcharfi; Menguy; Zamarlik [Synthetic Communications, 1993, vol. 23, # 21, p. 3019 - 3028]
[4]Yong, Rok Lee; Yun, Mi Kim [Helvetica Chimica Acta, 2007, vol. 90, # 12, p. 2401 - 2413]
[5]Gao, Feng; Ji, Peng; Meng, Xiang; Wang, Wei; Zeng, Fanxun; Zhang, Yueteng [Molecules, 2021, vol. 26, # 12]

11
[ 107-86-8 ]
[ 5927-18-4 ]
[ 52148-91-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 22℃;	To a suspension of NaH (60% in mineral oil, 4.20 g, 24.0 mmol) in anhydrous tetrahydrofuran* (300 mL) cooled to 0 C was added dropwise a solution of trimethylphosphonoacetate (17.0 mL, 19.1 g, 105 mmol) in anhydrous tetrahydrofuran* (40 mL). This solution was stirred at 0 C for 45 min and then treated with 3-methyl-2-butenal (10.0 mL, 8.72 g, 104 mmol) in one portion. The solution was allowed to warm to 22 oC and then stirred for 15 hours. After this time, the reaction mixture was diluted with diethyl ether (300 mL) and 2 N sulfuric acid (100 mL). The organics were separated, washed with saturated aqueous sodium bicarbonate solution (300 mL) and brine (350 mL), dried over magnesium sulfate, filtered and concentrated to a yellow oil. Purification by vacuum distillation afforded 3c (13.32 g, 91 %) of 95% purity by 1H NMR: bp 40-42 C; 1H NMR (500 MHz, CDCl3) d 7.59-7.53 (m, 1H), 5.98 (d, J = 11.6 Hz, 1H), 5.75 (d, J = 15.1 Hz, 1H), 3.73 (s, 3H), 1.88 (q, J = 9.1 Hz, 6H); 13C NMR (125 MHz, CDCl3) delta 168.0, 146.4, 141.1, 123.6, 118.0, 51.3, 26.5, 18.9.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 872 - 874
[2]Heterocycles,1984,vol. 21,p. 309 - 324

12
[ 107-86-8 ]
[ 4923-55-1 ]
[ 116513-69-0 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; 3-amino propanoic acid; In benzene; for 18h;Heating / reflux;	EXAMPLE 1: Synthesis of Compounds of Formulas I and IIICompounds of formula I may by synthesized by the following three stages: 1) synthesizing substituted 2- hydroxy-1, 4-naphthoquinones 1 (Figure 1); 2) generating a pyran ring (Figure 3) ; and 3) derivatizing the pyran ring (Figure 4) .Substituted 2-hydroxy-l, 4-naphthoquinones 1 may be synthesized from 1-tetralone derivatives 2 via the oxidation protocol described by Coombe, R. G. (Aust. J. Chem. (1974) 27:1327-30; Figure 1). The 1-tetralone derivatives 2 may be synthesized as shown in Figure 2 using procedures described in Coombe, R. G. (Aust. J. Chem. (1974) 27:1327-30; El-Ferlay et al . (Can. J. Chem. (1985) 63:2232-2236; Andrew et al . (Tetrahedron (1985) 41:2933-2938; Srinivas et al . (Organ. Proc. Res. Dev. (2004) 8:291-292; and Ferraz et al. (Tetrahedron (2003) 59:5817-5821.The pyran ring of the compounds of formula I may be synthesized as depicted in Figure 3, which shows the generation of formula III. Generally, a solution of 2- hydroxy-1, 4-naphthoquinone, 3-methyl-2-butenal (or related alpha, beta-unsaturated aldehyde, 1.25 equiv.), beta-alanine (0.15 equiv.), and acetic acid (0.375 mL/1 mmol napthoquinone) in benzene (15 mL/mmol naphthoquinone) is heated to reflux for 18 hours. The reaction mixture is then concentrated in vacuo. Flash chromatography (5%EtOAc: hexanes) affords the pyranonaphthoquinone product.Three exemplary methods for the synthesis of three pyran rings are provided below. <n="26"/>First, 2-hydroxy-l, 4-naphthoquinone was used with 3- methyl-2-butenal as the aldehyde to yield compound 8. The product spectra were identical to previously reported information for the same compound (see Lee et al . (Synthesis (2005) 18:3026-3034).8Second, 2-hydroxy-l, 4-naphthoquinone was used with (E) -methyl-4-oxobut-2-enoate as the aldehyde to provide compound 9. (E) -Methyl 4-oxobut-2-enoate was synthesized as described by Wolff et al . (Tetrahedron Lett. (2002) 43:2555-2559) .9Third, 2 , 5-Dihydroxy-l, 4-naphthoquinone was used with 3-methyl-2-butenal as the aldehyde to afford compound 10. The synthesis followed the procedure described by Oliveria et al . (Tetrahedron Lett. (1988) 29:155-158) .10Derivatization (i.e., adding substituents) of the pyran ring may be performed by derivatization techniques <n="27"/>described in the literature. For example, compounds 11- 14 were synthesized following the procedure described by Lee et al. (Synthesis (2005) 18:3026-3034).11Further derivatization of the pyran ring may be performed in accordance with the general procedure shown in Figure 4 and described in Lee et al. (Synthesis (2005) 18:3026-3034). Specifically, compounds 15-22 and related structures were synthesized by treating compound 14 with various nucleophiles (Xe, e.g., benzyl amine, allyl amine, butyl amine, and methanol) and Lewis acid reagents. <n="28"/>15 1617 1810 19 20

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 1706 - 1718
[2]Tetrahedron Letters,1988,vol. 29,p. 155 - 158
[3]Patent: WO2008/115804,2008,A1 .Location in patent: Page/Page column 24-28

13
[ 107-86-8 ]
[ 13485-59-1 ]
[ 151-50-8 ]
(S)-1-[(S)-2-(1-Cyano-3-methyl-but-2-enylamino)-propionyl]-pyrrolidine-2-carboxylic acid [ No CAS ]

Reference： [1]Tetrahedron Letters,1982,vol. 23,p. 3995 - 3998

14
[ 107-86-8 ]
[ 129319-71-7 ]
[ 129319-80-8 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 2661 - 2664

15
[ 107-86-8 ]
[ 5369-62-0 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Catalyst 10 (22.8mg, 0.06mmol) was added at rt to a solution of the alpha,beta-unsaturated aldehyde (0.3mmol) in MeOH (1.0mL). The mixture was stirred for 10min at rt followed by the addition of H2O2 (30% in H2O, 92muL, 0.9mmol). The reaction was stirred for 48h under argon. After completion, the reaction was cooled to 0C (ice bath) followed by the addition of NaBH4 (45.6mg, 1.2mmol). The reaction mixture was then stirred for a further 30min at 0C, and quenched with a pH=7.0 phosphate buffer solution. The aqueous phase was extracted with CH2Cl2 (3×5mL) and the combined organic extracts were dried over anhydrous MgSO4 and concentrated in vacuo after filtration. The crude product was purified by column chromatography (silica gel; petroleum ether/AcOEt=8:1) to give target compounds 2a-h
	With pyrrolidine; dihydrogen peroxide; In acetonitrile; for 1h;Cooling with ice;	3.41 g (40.5 mmol) of 3-methyl-2-butenal, 0.29 g (4.1 mmol) of pyrrolidine and 4.98 g (43.9 mmol) of 30% hydrogen peroxide water were added to 25 mL of acetonitrile under ice cooling and stirred for 1 hour to obtain 3 , 3-dimethyloxirane-2-carbaldehyde

Reference： [1]Liebigs Annalen der Chemie,1982,p. 49 - 67
[2]Organic Letters,2005,vol. 7,p. 3267 - 3270
[3]Angewandte Chemie - International Edition,2008,vol. 47,p. 1119 - 1122
[4]European Journal of Organic Chemistry,2009,p. 5653 - 5665
[5]Journal of Organic Chemistry,2011,vol. 76,p. 4617 - 4627
[6]Tetrahedron Asymmetry,2016,vol. 27,p. 294 - 300
[7]Patent: JP2017/95358,2017,A .Location in patent: Paragraph 0064
[8]Chemistry - A European Journal,2012,vol. 18,p. 11334 - 11342,9

16
[ 107-86-8 ]
[ 6258-60-2 ]
[ 151826-27-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With dmap In methanol Ambient temperature;
87%	With dmap In methanol at 20℃; for 18h;	A flask was charged with 3-methylbut-2-enal (2.00 mL, 20.3 mmol) and (4- methoxyphenyl)methanethiol (1.00 mL, 7.20 mmol). Methanol (5 mL) and DMAP (123 mg, 1.00 mmol) were added, and the reaction stirred at room temperature for 18 h. All the methanol was removed in vacuo, and the remaining residue taken up in toluene (10 ml). The solution was loaded onto a 40 g silica gel column. Elution with 0% to 40% ethyl acetate in heptane provided 3' (1.49 g, 6.25 mmol, 87% yield).

Reference： [1]Yoneda; Ota; Kawashima [Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 5, p. 876 - 881]
[2]Current Patent Assignee: ROCK CREEK ADVISORS LLC - WO2018/112176, 2018, A1 Location in patent: Paragraph 00374

17
[ 17721-06-1 ]
[ 107-86-8 ]
8-(2-Methyl-propenyl)-dithieno[3,2-b;2',3'-e]pyridine [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1996,vol. 33,p. 9 - 14

18
[ 107-86-8 ]
[ 143-33-9 ]
[ 25808-30-4 ]
N-Cyanomethyl-N-(1-cyano-3-methylbut-2-enyl)methylamine [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 2919 - 2923

19
[ 107-86-8 ]
[ 84-85-5 ]
[ 573-13-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With phenylboronic acid In acetic acid; toluene for 4h; Heating;
95%	With acetic acid; phenylboronic acid In toluene for 16h; Heating;
79%	With ethylenediaminediacetic acid In chloroform at 60℃; for 24h;

60%	In chloroform for 24h; Heating;
60%	With ethylenediamine diacetic acid In chloroform at 20℃; for 24h; Inert atmosphere; Reflux;
56%	With 1,2-diamino-benzene In dichloromethane at 40℃; for 60h; Inert atmosphere; Molecular sieve;	4. General Procedure for the Synthesis of 2H-Benzo[h]Chromene 3 General procedure: Dry CH2Cl2 (1.0 mL) was added to a mixture of o-phenylenediamine (IX, 0.04 mmol),enal 1 (0.30 mmol) and arylol 2 (0.20 mmol) under Ar. The reaction was stirred at 40 Cuntil the completion of 2 monitored by TLC. Then, the mixture was applied to columnchromatography directly and eluted with ethyl ether and hexane (9/1) to give product 3.

Reference： [1]Alves, Glaucia B. C.; Lopes, Rosangela S. C.; Lopes, Claudio C.; Snieckus, Victor [Synthesis, 1999, # 11, p. 1875 - 1877]
[2]Chauder, Brian A.; Lopes, Claudio C.; Lopes, Rosangela S. C.; Da Silva, Alcides J. M.; Snieckus, Victor [Synthesis, 1998, # 3, p. 279 - 282]
[3]Cadelis, Melissa M.; Barker, David; Copp, Brent R. [Synlett, 2012, vol. 23, # 20, p. 2939 - 2942]
[4]Yong, Rok Lee; Yun, Mi Kim [Helvetica Chimica Acta, 2007, vol. 90, # 12, p. 2401 - 2413]
[5]Location in patent: experimental part Wang, Xue; Chen, Ye; Lee, Yong Rok [Bulletin of the Korean Chemical Society, 2011, vol. 32, # 1, p. 153 - 156]
[6]Gao, Feng; Ji, Peng; Meng, Xiang; Wang, Wei; Zeng, Fanxun; Zhang, Yueteng [Molecules, 2021, vol. 26, # 12]

20
[ 19131-99-8 ]
[ 107-86-8 ]
(S)-N-methyl-N-(3-methylbuta-1,3-dienyl)-1-phenylethylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium carbonate In benzene at 20℃; for 24h;

Reference： [1]Serebryakov; Nigmatov; Shcherbakov; Struchkova [Russian Chemical Bulletin, 1998, vol. 47, # 1, p. 82 - 90]

21
[ 107-86-8 ]
[ 95-01-2 ]
[ 54287-99-9 ]
[ 33279-69-5 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1999,vol. 72,p. 259 - 263

22
[ 556-82-1 ]
[ 18511-56-3 ]
[ 5369-62-0 ]
[ 107-86-8 ]

Reference： [1]Journal of Physical Chemistry B,1998,vol. 102,p. 7126 - 7131
[2]Journal of Physical Chemistry B,1998,vol. 102,p. 7126 - 7131

23
[ 107-86-8 ]
[ 95-01-2 ]
[ 54287-99-9 ]

Yield	Reaction Conditions	Operation in experiment
50%	With calcium hydroxide; In methanol; at 20℃; for 48h;	2,4-Dihydroxybenzaldehyde (15) (3 g/20.17 mmol), calcium hydroxide (1.543 g/20.8 mmol) and 150 mL of methanol were place in a two-necked round-bottom flask. Then, prenal (9.135 g/108.6 mmol) was added dropwise. The mixture was allowed to stir at room temperature for 48 h. The reaction was quenched with HCl 1 M until pH 1-2. The methanol was evaporated and the aqueous phase was extracted with 3 × 150 mL of ethyl acetate. The organic phase was washed with 2 × 100 mL of brine, dried over sodium sulfate anhydrous, filtered and the organic solvent evaporated. The crude product was purified by silica gel flash chromatography (n-hexane/ethyl acetate 9:1). Compound 16 was crystallized from n-hexane/ethyl acetate 3:1 as a yellow solid (2.06 g/50%).
50%	With calcium hydroxide; In methanol; at 20℃; for 48h;	2,4-Dihydroxybenzaldehyde (42) (3g/20.17mmol), calcium hydroxide (1.543g/20.8mmol) and 150mL of methanol were placed in a round-bottom flask. Then, prenal (9.135g/108.6mmol) was added dropwise. The mixture was stirred at room temperature for 48h. The reaction was quenched with HCl 1M until pH 1-2. The methanol was evaporated and the aqueous phase was extracted with 3×150mL of ethyl acetate. The organic phase was washed with 2×100mL of brine, dried over sodium sulfate anhydrous, filtered and the organic solvent evaporated. The crude product was purified by silica gel flash chromatography (n-hexane/ethyl acetate 9:1). Compound 43 was crystallized from n-hexane/ethyl acetate 3:1 as a yellow solid (2.06g/50%).6-Formyl-5-hydroxy-2,2-dimethyl-2H-benzopyran (43). Mp: 68-69C. IR numax (cm-1) (KBr): 3464, 2967, 2922, 2857, 1628, 1484, 1330, 1294, 1247, 1176, 1107, 1081, 748. 1H NMR (300.13MHz, CDCl3) delta (ppm): 11.65 (OH), 9.66 (s, CHO), 7.29 (d, J=8.6), 6.88 (d, J=10.0), 6.44 (d, J=8.6), 5.61 (d, J=10.0), 1.46 (s, 6H). 13C NMR (100.63MHz, CDCl3) delta (ppm): 194.5, 160.6, 158.7, 134.7, 128.6, 115.2, 115.1, 109.4, 108.8, 78.2, 28.4. EIMS m/z (%): 205 (5, [M+1]+.), 204 (10 [M]+.), 190 (15), 189 (100), 187 (60), 159 (12), 131 (12), 103 (10), 77 (12), 51 (6). HRMS (ESI) m/z calcd for C12H13O3 [M+H]+: 205.08570, found: 205.08592.
21%	With pyridine; at 140℃; for 10h;	Weigh compound 18-1 (2g, 14.5mmol) in pyridine (2.5mL), Add 3-methyl-2-butenal (2.78 mL, 28.8 mmol), The system was reacted at 140 C for 10 hours. After the reaction was completed, The solvent was distilled off under reduced pressure, The residue was purified by column chromatography (eluent: petroleum ether / ethyl acetate = 300: 5-300: 10), Compound 18-2 (brown oil, 31 mg) was obtained.

0.68 g

With calcium hydroxide; In methanol; at 20℃; for 12h;

A 1 g portion of 2,4-2 hydroxybenzaldehyde (Compound 2 shown in Figure 1)0.514 g Ca (OH) 2, methanol150mL.3.045 g of prenyl aldehyde (compound 1 shown in FIG. 1) was then added dropwise.Stir at room temperature for 12h.Quench with HCl (1 M) until the pH is 1-2.Methanol was evaporated and the aqueous phase was extracted with 3 * 150 mL of ethyl acetate.The organic phase was washed with 2 * 100 mL saturated brine, dried over anhydrous Na2SO4,Vacuum filtration, and spin dry. The crude product was passed through a column of silica gel (petroleum ether: ethyl acetate = 9: 1)Crystallization gave product 3 (0.68 g) as shown in FIG.

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 9266 - 9286
[2]Journal of Organic Chemistry,2015,vol. 80,p. 11460 - 11467
[3]Angewandte Chemie - International Edition,2012,vol. 51,p. 8092 - 8096
[4]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 2941 - 2959
[5]European Journal of Medicinal Chemistry,2013,vol. 69,p. 798 - 816
[6]Tetrahedron,2001,vol. 57,p. 5335 - 5338
[7]Patent: CN110627817,2019,A .Location in patent: Paragraph 0328-0331
[8]Tetrahedron Letters,2009,vol. 50,p. 5075 - 5079
[9]Advanced Synthesis and Catalysis,2005,vol. 347,p. 555 - 562
[10]Patent: CN106187974,2016,A .Location in patent: Paragraph 0044

24
[ 107-86-8 ]
[ 81-54-9 ]
[ 345969-42-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 607 - 612

25
[ 556-82-1 ]
[ 541-47-9 ]
[ 107-86-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium acetate In water at 100℃; for 10h;
	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; titanium(IV) oxide In benzotrifluoride for 8h; Irradiation;
	With oxygen In water at 20℃; for 336h;

Reference： [1]Ten Brink, Gerd-Jan; Arends, Isabel W. C. E.; Sheldon, Roger A. [Advanced Synthesis and Catalysis, 2002, vol. 344, # 3-4, p. 355 - 369]
[2]Zhang, Miao; Wang, Qi; Chen, Chuncheng; Ma, Wanhong; Zhao, Jincai; Zang, Ling [Angewandte Chemie - International Edition, 2009, vol. 48, # 33, p. 6081 - 6084][Angewandte Chemie, 2009, vol. 121, # 33, p. 6197 - 6200]
[3]Location in patent: experimental part Tonucci, Lucia; Nicastro, Marco; D'Alessandro, Nicola; Bressan, Mario; D'Ambrosio, Primiano; Morvillo, Antonino [Green Chemistry, 2009, vol. 11, # 6, p. 816 - 820]

26
[ 410087-91-1 ]
[ 107-86-8 ]
[ 83067-20-3 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 5689 - 5698

27
[ 763-32-6 ]
[ 107-86-8 ]

Yield	Reaction Conditions	Operation in experiment
68%	With molecular sieve; pyridinium chlorochromate In dichloromethane at 20℃; for 4h;
51.1%	With oxygen In para-xylene at 130℃; for 6h;	3 EXAMPLE 3Oxidation of Isoprenol to Prenal by the Process According to the InventionIn a round-bottom flask with a reflux condenser, the catalyst (510 mg, 1.5% by weight of Au/hydrotalcite) was added to a solution of isoprenol (550 mg, 6.4 mmol) in p-xylene (25 mL), and the reaction was blanketed with air at 130° C. and stirred for 6 h. Filtration of the catalyst gave 16.8 g of a yellowish liquid of the following composition: 1.63% by weight of prenal (3-methylbut-2-en-1-al, 3.27 mmol), 1.42% by weight of isoprenol (2.79 mmol), corresponding to 56.4% conversion, 88.1% selectivity and 51.1% yield.
62.2 %Chromat.	With [Ru(PnOct₃)₄(H)₂] In cyclohexanone at 120℃; for 20h; Reflux; Inert atmosphere; Schlenk technique;	I.b.1 I.b. Dehydrogenation of isoprenol I.b. Dehydrogenation of isoprenolI.b.1 A solution of isoprenol (1.0 g, 11.6 mmol) and [Ru(Pn-Oct3)4(H)2] (200 mg, 0.13 mmol) in 15 g cylohexanone was stirred at 120°C for 20 hours under inert conditions (argon atmosphere) in a Schlenk-flask (50 mL) equipped with a reflux condenser. After cooling to room temperature, the reaction mixture was analyzed by GC revealing the following percentage composition (based on the area percents of the respective peaks): prenol 0 %, prenal 62.2 %, 3-methyl-butan-1-ol 0 %, isoprenol 37.1 %, iso-valeraldehyde 0 %.

	Multi-step reaction with 2 steps 1: bis-μ-dichloro(1,5-cyclooctadiene)ruthenium(II); 1-butyl-3-methylimidazolium chloride; potassium <i>tert</i>-butylate; tricyclohexylphosphine / toluene / 12 h / Reflux; Inert atmosphere; Schlenk technique 2: [Ru(PnOct₃)₄(H)₂] / 20 h / 120 °C / Reflux; Inert atmosphere; Schlenk technique
62.2 %Chromat.	With [Ru(PnOct₃)₄(H)₂] In cyclohexanone at 120℃; for 20h; Inert atmosphere; Schlenk technique;	I.b.1 I.b. Dehydrogenation of isoprenol I.b. Dehydrogenation of isoprenolI.b.1 A solution of isoprenol (1.0 g, 11.6 mmol) and [Ru(Pn-Oct3)4(H)2] (200 mg, 0.13 mmol) in 15 g cylohexanone was stirred at 120°C for 20 hours under inert conditions (argon atmosphere) in a Schlenk-flask (50 mL) equipped with a reflux condenser. After cooling to room temperature, the reaction mixture was analyzed by GC revealing the following percentage composition (based on the area percents of the respective peaks): prenol 0 %, prenal 62.2 %, 3-methyl-butan-1-ol 0 %, isoprenol 37.1 %, iso-valeraldehyde 0 %.
	Multi-step reaction with 2 steps 1: bis-μ-dichloro(1,5-cyclooctadiene)ruthenium(II); 1-butyl-3-methylimidazolium chloride; potassium <i>tert</i>-butylate; tricyclohexylphosphine / toluene / 12 h / Reflux; Inert atmosphere 2: [Ru(PnOct₃)₄(H)₂] / 20 h / 120 °C / Inert atmosphere; Schlenk technique
	Multi-step reaction with 2 steps 1: 5%-palladium/activated carbon; oxygen / 5 h / 80 °C / 3750.38 Torr 2: oxygen; / 5 h / 60 °C / 15001.5 Torr

Reference： [1]Fernandes, Rodney A.; Kumar, Pradeep [Tetrahedron Letters, 2003, vol. 44, # 6, p. 1275 - 1278]
[2]Current Patent Assignee: BASF SE - US2011/4025, 2011, A1 Location in patent: Page/Page column 3
[3]Current Patent Assignee: BASF SE - EP2597081, 2013, A1 Location in patent: Paragraph 0124
[4]Current Patent Assignee: BASF SE - EP2597081, 2013, A1
[5]Current Patent Assignee: BASF SE - WO2013/76226, 2013, A1 Location in patent: Page/Page column 25
[6]Current Patent Assignee: BASF SE - WO2013/76226, 2013, A1
[7]Current Patent Assignee: BASF SE - US2019/77736, 2019, A1

28
[ 40899-71-6 ]
[ 107-86-8 ]
3-methyl-1-[1-(phenylsulfonyl)-1H-indol-2-yl]but-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 2:To a solution of 8a1 (52.1 g, 0.20 mol) in anhydrous THF (1.5 L) at -78C is added a solution of t-BuLi (1.7M in pentane, 157 mL). The resulting solution is stirred at - 78C for 1 h and then a solution of 3-methyl-2-butenal (25.4 mL) in anhydrous THF (350 mL) is added over a period of 30 min. The reaction mixture is stirred at -78C for 45 min. After warming to RT, the reaction mixture is quenched by saturated NH4CI (~1.5L), and extracted with EtOAc. The combined organic layers are washed with brine, dried over Na2S04 and concentrated in vacuo to provide crude 8a2 that is used as such.
		Step 2:To a solution of 57a1 (52.1 g, 0.20 mol) in anhydrous THF (1.5 L) at -78C is added a solution of t-BuLi (1.7M in pentane, 157 mL). The resulting solution is stirred at - 78C for 1 h, and then a solution of 3-methyl-2-butenal (25.4 mL) in anhydrous THF (350 mL) is added over a period of 30 min. The reaction mixture is stirred at -78C for 45 min. After warming to RT, the reaction mixture is quenched with saturated NH4CI (~1.5L) and extracted with EtOAc. The combined organic layers are washed with brine, dried over Na2S04 and concentrated in vacuo to provide crude 57a2 which is used as such.

Reference： [1]Journal of Heterocyclic Chemistry,2003,vol. 40,p. 289 - 295
[2]Patent: WO2013/26162,2013,A1 .Location in patent: Page/Page column 45
[3]Patent: WO2013/26163,2013,A1 .Location in patent: Page/Page column 69-70

29
[ 107-86-8 ]
[ 89043-32-3 ]
[ 850095-06-6 ]

Reference： [1]Molecules,2004,vol. 9,p. 541 - 549

30
[ 107-86-8 ]
[ 24019-66-7 ]
8-allyl-2,2-dimethyl-2H-chromene-3-carbaldehyde [ No CAS ]
(1RS,9RS,11RS)-6-allyl-9-methyl-8,12-dioxatricyclo[7.3.1.0^2,7]tri-deca-2,4,6-trien-11-ol [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2005,vol. 347,p. 555 - 562
[2]Advanced Synthesis and Catalysis,2005,vol. 347,p. 555 - 562

31
[ 107-86-8 ]
[ 14562-10-8 ]
8-phenyl-2,2-dimethyl-2H-chromene-3-carbaldehyde [ No CAS ]
(1RS,9RS,11SR)-9-methyl-6-phenyl-8,12-dioxatricyclo[7.3.1.0^2,7]tri-deca-2,4,6-trien-11-ol [ No CAS ]
(1RS,9RS,11RS)-9-methyl-6-phenyl-8,12-dioxatricyclo[7.3.1.0^2,7]tri-deca-2,4,6-trien-11-ol [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2005,vol. 347,p. 555 - 562
[2]Advanced Synthesis and Catalysis,2005,vol. 347,p. 555 - 562

32
[ 107-86-8 ]
[ 41602-56-6 ]
(1RS,9RS,11RS)-5-N,N-dimethylamino-9-methyl-8,12-dioxatricyclo[7.3.1.0^2,7]tri-deca-2,4,6-trien-11-ol [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2005,vol. 347,p. 555 - 562

33
[ 930-88-1 ]
[ 107-86-8 ]
[ 7223-30-5 ]
N-(2,3,3a,4,7,7a-hexahydro-2,6-dimethyl-1,3-dioxo-1H-isoindol-4-yl)-3-phenylpropiolamide [ No CAS ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 11333 - 11344

34
[ 2732-18-5 ]
[ 107-86-8 ]
[ 130364-30-6 ]
[ 57601-61-3 ]
[ 31525-75-4 ]

Reference： [1]Journal of Natural Products,2005,vol. 68,p. 78 - 82
[2]Asian Journal of Chemistry,2013,vol. 25,p. 3629 - 3632

35
[ 107-86-8 ]
[ 2524-37-0 ]
[ 705260-25-9 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 7539 - 7543

36
[ 18829-55-5 ]
[ 107-86-8 ]
2-butyl-4-methyl-benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With manganese(IV) oxide In acetonitrile at 81℃; for 10h;

Reference： [1]Hong, Bor-Cherng; Tseng, Hsing-Chang; Chen, Shang-Hung [Tetrahedron, 2007, vol. 63, # 13, p. 2840 - 2850]

37
[ 1576-87-0 ]
[ 107-86-8 ]
2-ethyl-4-methyl-benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With manganese(IV) oxide In acetonitrile at 81℃; for 6h;

Reference： [1]Hong, Bor-Cherng; Tseng, Hsing-Chang; Chen, Shang-Hung [Tetrahedron, 2007, vol. 63, # 13, p. 2840 - 2850]

38
[ 107-86-8 ]
[ 91506-06-8 ]
[ 461045-38-5 ]
3-{3-[1-hydroxy-5-(3-methyl-but-2-enylidene)-4-oxo-cyclopent-2-enyl]-prop-1-ynyl}-<i>N</i>,<i>N</i>-dimethyl-benzamide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2006,vol. 12,p. 1368 - 1376

39
[ 107-86-8 ]
[ 3602-54-8 ]
[ 25983-76-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With ethylenediamine diacetic acid In toluene for 12h; Heating;
95%	With ethylenediamine diacetic acid In xylene for 10h; Heating;
95%	With ethylenediamine diacetic acid In toluene Reflux; Inert atmosphere;

90%	With calcium hydroxide In methanol for 18h; Reflux;
90%	With calcium hydroxide In methanol at 20℃; for 10h; Reflux; Inert atmosphere;
68%	With ethylenediamine diacetic acid In 5,5-dimethyl-1,3-cyclohexadiene at 170℃; for 1h; Microwave irradiation;
53.5%	With ethylenediaminediacetic acid In 5,5-dimethyl-1,3-cyclohexadiene at 170℃; for 1h; Microwave irradiation;	5 Synthesis of 1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-ethanone (ENDF 4) A solution of 2′4′-Dihydroxy-6′-methoxyacetophenone (100 mg, 0.55 mmol), 3-methyl-2-butenal (180.6 mg, 0.64 mmol) and ethylenediamine-N,N′-diacetic acid (EDDA) (9.89 mg, 0.05 mmol) in xylene (5 ml) was radiated in a 10 ml microwave vial with snap-on cap at 170° C. for 60 min. The reaction mixture was given to water and was extracted with ethyl acetate, washed with brine and dried over sodium sulfate. The solution was concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/hexane: 4/1) to give 74.0 mg (53.5%) of a yellow solid, M=248. g/mol (C14H16O4) (Lee, Xia. Synthesis-Stuttgart 2007, (20), 3240-3246). 1H-NMR (acetone): δ(ppm): 1.29 (s, 6H, 2×CH3), 2.42 (s, 3H, COCH3), 3.79 (s, 3H2OCH3) 5.42 (d, J=9.84, 1H, Hz H-4′), 5.85 (s, 1H, H-5), 6.45 (d, J=9.88 Hz, 1H, H-5′) 13C-NMR (CDCl3): 204.01 (CO), 164.21 (C-4), 162.55 (C-5), 161.21 (C-2), 126.42 (C-4′), 116.40 (C-5′), 106.21 (C-3), 103.14 (C-1), 92.14 (C-2′), 78.81 (?), 56.35 (CH3), 33.09 (OCCH3), 28.54 (2×CH3)

Reference： [1]Yong, Rok Lee; Wang, Xue; Xia, Likai [Molecules, 2007, vol. 12, # 7, p. 1420 - 1429]
[2]Yong, Rok Lee; Xia, Likai [Synthesis, 2007, # 20, p. 3240 - 3246]
[3]Location in patent: experimental part Xia, Likai; Lee, Yong Rok [Bulletin of the Korean Chemical Society, 2012, vol. 33, # 6, p. 2087 - 2090]
[4]Wang, Xue; Lee, Yong Rok; Kim, Sung Hong [Bulletin of the Korean Chemical Society, 2012, vol. 33, # 8, p. 2647 - 2650]
[5]Xia, Likai; Rok Lee, Yong [Helvetica Chimica Acta, 2013, vol. 96, # 4, p. 644 - 650]
[6]Aigner, Ludwig; Bieler, Lara; Couillard-Despres, Sebastien; Priglinger, Eleni; Riepl, Herbert M.; Urmann, Corinna [Journal of Natural Products, 2021, vol. 84, # 10, p. 2675 - 2682]
[7]Current Patent Assignee: COUILLARD DESPRES; AIGNER - US9527860, 2016, B2 Location in patent: Page/Page column 38

40
[ 556-82-1 ]
2-hydroperoxy-3-methyl-3-buten-1-ol [ No CAS ]
C₅H₁₀O₃ [ No CAS ]
[ 5369-62-0 ]
[ 107-86-8 ]

Reference： [1]Photochemistry and Photobiology,2006,vol. 82,p. 1226 - 1232

41
[ 107-86-8 ]
[ 76287-49-5 ]
1-(4-heptylphenyl)-3-methylbut-2-en-1-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5269 - 5280

42
[ 107-86-8 ]
[ 604-44-4 ]
[ 101096-00-8 ]

Reference： [1]Helvetica Chimica Acta,2007,vol. 90,p. 2401 - 2413

43
[ 107-86-8 ]
[ 89599-01-9 ]
3-bromo-N-(3-methyl-but-2-enoyl)-benzenesulfonamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 14106 - 14107

44
[ 107-86-8 ]
[ 19013-07-1 ]

Reference： [1]Synthetic Communications,1994,vol. 24,p. 1009 - 1018

45
[ 107-86-8 ]
[ 55876-82-9 ]

Reference： [1]Journal of Chemical Research, Miniprint,1985,p. 2801 - 2817

46
[ 5272-33-3 ]
[ 107-86-8 ]

Reference： [1]Tetrahedron Letters,1981,vol. 22,p. 2021 - 2022

47
[ 107-86-8 ]
[ 51746-85-1 ]
[ 261765-52-0 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In tetrahydrofuran; for 24h;Heating / reflux;	To a solution of 4-pyridin-3-yl-imidazole (1 g) in THF (34 ML) was added acetic acid (1.6 ML) and 3-methyl-2-butenal (3.3 ML) and the resulting solution was heated under gentle reflux for 24 hours. THF was then removed in vacuo and the residue was purified on a Flash 75 long column eluding with MeOH-CH2Cl2 to give the title compound as slightly yellow oil. MS: m/z 230 (M+H).
	With acetic acid; In tetrahydrofuran;	EXAMPLE 15 3,3-Dimethyl-3(4-Pyridin-3-yl-imidazol-1-yl)-propioaldehyde To a solution of 4-pyridin-3-yl-imidazole (1 g) in THF (34 mL) was added acetic acid (1.6 mL) and 3-methyl-2-butenal (3.3 mL) and the resulting solution was heated under gentle reflux for 24 hours. THF was then removed in vacuo and the residue was purified on a Flash 75 (silica gel column made by Biotage Division of Dyax Corp, U.S.) long column eluding with MeOH-CH2Cl2 to give the title compound as slightly yellow oil. MS: m/z 230 (M+H).
	With acetic acid; In tetrahydrofuran;	Example 15 3,3-Dimethyl-3-(4-pyridin-3-yl-imidazol-1-yl)-propioaldehyde To a solution of 4-pyridin-3-yl-imidazole (1 g) in THF (34 mL) was added acetic acid (1.6 mL) and 3-methyl-2-butenal (3.3 mL) and the resulting solution was heated under gentle reflux for 24 hours. THF was then removed in vacuoand the residue was purified on a Flash 75 long column eluding with MeOH-CH2Cl2to give the title compound as slightly yellow oil. MS: m/z 230 (M+H).

Reference： [1]Patent: US6664238,2003,B1 .Location in patent: Page column 26
[2]Patent: US6420343,2002,B1
[3]Patent: EP1298138,2003,A1

48
[ 581-43-1 ]
[ 107-86-8 ]
3,3-dimethyl-3H-naphtho[2,1-b]pyran-8-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With pyridine; for 3.5h;Heating / reflux;	Step 1: 3,3-Dimethyl-3H-naphtho[2,1-b]pyran-8-ol A mixture of 2, 6-dihydroxynaphthalene (50. 0 g, 0, 312 mol), 3-methyl-2-butenal (30 mL, 26. 24 go 0. 312 mol) and pyridine (38 mi., 37. 02 go 0.468 mol) were heated under reflux fur 3. 5 h. The mixture was cooled to room temperature, diluted with dichloromethane (500 mL), filtered through a sintered glass funnel (porosity 3) then washed with aqueous hydrochloric acid solution (1 M, 2 x 250 rnL) and water (1 x 250 mL). The organic layer was extracted with a solution of aqueous sodium hydroxide (2 M, 1 x 250 mol and 1 x 125 mL) and the combined aqueous extracts cooled in an ice-salt bath, acidified (with stirring) with aqueous hydrochloric acid solution (5 M) until a creamy-white precipitate formed (pH No. 2). The solid was stirred for an additional 10 mm with cooling, collected by filtration, washed with water and dried under high vacuum at 40 to to afford the desired crude product ELS a fluffy white-grey solid (43. 9 g, 62 %). The crude product was used in the. subsequent reaction without further purification. Recrystallised from dicthyt etherlhexane m. p. 120-123. No. (1H) (300 MHz, CDCl3) 1.47, s, 2xCH3 ; 4.77, s, OH; 5.71, d, J 10.2 Hz, H2 ; 6. 97, d, J 10.2 Hz, H1; 7.02, d, J 8.7 Hz, H5; 7. 08, s, H7; 7.10, dd, J 8. 7, 2.7 Hz, H9; 7. 48, d, J 8.7 Hz, H6; 7. 85, d, J 8.7 Hz, H10. Sz (ES+, 100 V) 471 (2M+H+H2O, 100%), 245 (M+H+H2O, 62), 227 (M+H, 63)
62%		Step 1: 3,3-Dimethyl-3H-naphtho[2,1-b]pyran-8-ol A mixture of 2,6-dihydroxynaphthalene (50.0 g, 0.312 mol), 3-methyl-2-butenal (30 mL, 26.24 g, 0.312 mol) and pyridine (38 mL, 37.02 g, 0.468 mol) were heated under reflux for 3.5 h. The mixture was cooled to room temperature, diluted with dichloromethane (500 mL), filtered through a sintered glass runnel (porosity 3) then washed with aqueous hydrochloric acid solution (1 M, 2250 mL) and water (1250 mL). The organic layer was exracted with a solution of aqueous sodium hydroxide (2 M, 1250 mL and 1125 mL) and the combined aqueous extracts cooled in an ice-salt bath, acidified (with stirring) with aqueous hydrochloric acid solution (5 M) until a creamy-white precipitate formed (pH ~2). The solid was stirred for an additional 10 min with cooling, collected by filtration, washed with water and dried under high vacuum at 40 C. to afford the desired crude product as a fluffy white-grey solid (43.9 g, 62%). The crude product was used in the subsequent reaction without further purification. Recrystallized from diethyl ether/hexane m.p. 120-123. delta (1H) (300 MHz, CDCl3)1.47, s; 2*CH3; 4.77, s, OH; 5.71, d, J 10.2 Hz, H2; 6.97, d, J 10.2 Hz, H1; 7.02, d, J 8.7 Hz, H5; 7.08, s, H7; 7.10. dd, J 8.7. 2.7 Hz, H9; 7.48, d, J 8.7 Hz, H6; 7.85, d, J 8.7 Hz, H10. m/z (ES-, 100 V) 471 (2M+H+H2O, 100%), 245 (M+H+H2O, 62), 227 (M+H, 63).
	With pyridine; for 3.5h;Reflux;	A mixture of 2,6-dihydroxynaphthalene 20 (50.0 g, 0.312 mol), 3-methyl-2-butenal (30 mL, 26.24 g, 0.312 mol) and pyridine (38 mL, 37.02 g, 0.468 mol) were heated under reflux for 3.5 h. The mixture was cooled to room temperature, diluted with dichloromethane (500 mL), filtered through a sintered glass funnel (porosity 3) then washed with aqueous hydrochloric acid (1 M, 2 x 250 mL) and water (1 x 250 mL). The organic layer was extracted with a solution of aqueous sodium hydroxide (2 M, 1 x 250 mL and 1 x 125 mL) and the combined aqueous extracts cooled in an ice-salt bath, acidified (with stirring) with aqueous hydrochloric acid (5 M) till a creamy-white precipitate forms (pH ~ 2). The solid was stirred for an additional 10 min with cooling, collected by filtration, washed (water) and pumped dry under high vacuum @ 40 C to afford the desired crude product as a fluffy white-grey solid (43.9 g, 62 %). The crude product could be used in the subsequent reaction without further purification. The product recrystallised from diethyl ether/hexanes as a slightly pink solid, m.p. 120-123 C. max 3424 (s), 2980 (w), 1622 (m), 1520 (m) cm-1. 1H NMR (300 MHz, CDCl3) 1.47 (6H, s, C-CH3), 4.77 (1H, br s, OH), 5.71 (1H, d, 10, H2), 6.97 (1H, d, 10, H1), 7.02 (1H, d, 8.5, H5), 7.08 (1H, br s, H7), 7.10 (1H, dd, 8.5, 2.5, H9), 7.48 (1H, d, 8.5, H6), 7.85 (1H, d, 8.5, H10). ESI-MS (positive, 100 V) 471 (2M+H+H2O, 100%), 245 (M+H+H2O, 62), 227 (M+H, 63). HR-ESI-MS (positive) Calcd. for C43H33O11+ 227.1070; found 227.1072

Reference： [1]Patent: WO2005/95376,2005,A1 .Location in patent: Page/Page column 26-27
[2]Patent: US2009/170926,2009,A1 .Location in patent: Page/Page column 9
[3]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1644 - 1648

49
[ 107-86-8 ]
[ 582-17-2 ]
[ 57309-93-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridine at 110℃; for 20h;	9.1 Compound 10: 8-Bromo-3,3-dimethyl-9-(4-methylbenzenesulfonyloxy)-3H-naphtho[2,1- b]pyran-7,10-dione Step 1 3, 3-Dimethyl-3H-naphtho[2,1-b]pyran-9-ol A mixture of 2,7-dihydroxynaphthalene (33.2 g, 207 mmol), 3-methyl-2-butenal (20. 0 mL, 207 tnmol) and pyridine (17.0 iiiL,,) was heated at 110 or 2 () h under nitrogen. The mixture was coolcd to room temperature and diluted with diethyl ether (150 mL). The organic phusc was separated and washed successively with aqueous sulphuric acid solution (5%, 150 mL), water (150 mL), aqueous sodium hydrogen carbonate solution (5%, 150 nL) and water (150 mL). The organic phase was dried, filtered and concentrated n vucuo to afford 3, 3-dimethyl-3H-naphtho[2,1-b]pyran-9-ol as a buff coloured solid (43. 1 g, 92%): 1H NMR (300 MHz, CDCl3) No. 1.48 (6H, s, 2 x CH3), 4.99 (1H, br s, OH), 5.67 (1H, d, J=10 Hz, H2), 6.84-6.93 (3H, m, H1, H5, H8), 7.23 (1H, d, J2.3 = Hz, H10), 7.55 (1H, d, J=8.8 Hz, H6), 7. 63 (111, d, J = 8. 8 Hz, H7). m/z (FAB, 3NBA/MeOH) 227 (M+H, 68%)
92%	With pyridine at 110℃; for 0.333333h;	9.1 A mixture of 2,7-dihydroxynaphthalene (33.2 g, 207 mmol), 3-methyl-2-butenal (20.0 mL, 207 mmol) and pyridine (17.0 mL) was heated at 110° C. for 20 h under nitrogen. The mixture was cooled to room temperature and diluted with diethyl ether (150 mL). The organic phase was separated and washed successively with aqueous sulphuric acid solution (5%, 150 ml,), water (150 mL), aqueous sodium hydrogen carbonate solution (5%, 150 mL) and water (150 mL). The organic phase was dried, filtered and concentrated in vacuo to afford 3,3-dimethyl-3H-naphtho[2,1-b]pyran-9-ol as a buff coloured solid (43.1 g, 92%): 1H NMR (300 MHz, CDCl3) δ 1.48 (6H, s, 2*CH3), 4.99 (1H, br s, OH), 5.67 (1H, d, J=10 Hz, H2), 6.84-6.93 (3H, m, H1, H5, H8), 7.23 (1H, d, J 2.3=Hz, H10), 7.55 (1H, d, J=8.8 Hz, H6), 7.63 (1H, d, J=8.8 Hz, H7). m/z (FAB, 3NBA/MeOH) 227 (M+H, 68%).
73%	With pyridine at 120℃; for 20h;

Reference： [1]Current Patent Assignee: MONASH UNIVERSITY - WO2005/95376, 2005, A1 Location in patent: Page/Page column 35
[2]Current Patent Assignee: MONASH UNIVERSITY - US2009/170926, 2009, A1 Location in patent: Page/Page column 12
[3]Crosby, Ian T.; Rose, Mark L.; Collis, Maree P.; De Bruyn, Paula J.; Keep, Philip L. C.; Robertson, Alan D. [Australian Journal of Chemistry, 2008, vol. 61, # 10, p. 768 - 784]

50
[ 107-86-8 ]
[ 122-51-0 ]
[ 99-93-4 ]
[ 19013-07-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In ethanol; para-xylene;	Production of 6-acetyl-2,2-dimethyl-2H-1-benzopyran 60 mg undried catalyst KP-10 (Sud-Chemie) and 35.8 g triethyl orthoformate were placed in a flask in 45 ml absolute ethanol in an argon atmosphere. While cooling 19.56 g 3-methyl-crotonaldehyde was added in drops over 30 minutes at 5 C. Then the reaction mixture was stirred for a further hour at 5 C. After adding 195 mg potassium carbonate, 100 ml xylol and 20.95 g 4-hydroxy-acetophenone, the reaction mixture was heated for an hour to 140 C. and the ethanol formed was continuously distilled off. The solution was stirred for a further 4 hours at 140 C. After cooling, the organic phase was washed with NaOH (5%) and concentrated. The raw product was distilled under high vacuum (0.5mbar/98 C.). The fractions of the said compound obtained had a content of 76.4% (0.91 g) and 94.3% (15.8 g) (51.8% yield).

Reference： [1]Patent: US5919953,1999,A

51
[ 107-86-8 ]
[ 1191-16-8 ]
[ 5392-40-5 ]

Yield	Reaction Conditions	Operation in experiment
48%	With benzoic acid	17 EXAMPLE 17 EXAMPLE 17 60 parts of prenyl acetate, 40 parts of 3,3-dimethylacrolein and 2parts of benzoic acid are heated together for five hours thirty minutes at 140°C and the product is worked up. 11.1 parts of citral is obtained having a boiling point of 104°C at 12 mm in a yield of 48% at a conversion of 32% (based on 3,3-dimethylacrolein).

Reference： [1]Current Patent Assignee: BASF SE - US3965193, 1976, A

52
[ 107-86-8 ]
[ 24019-66-7 ]
8-allyl-2,2-dimethyl-2H-chromene-3-carbaldehyde [ No CAS ]
C₁₅H₁₈O₃ [ No CAS ]

Reference： [1]Synlett,2009,p. 550 - 553

53
[ 107-86-8 ]
[ 14562-10-8 ]
8-phenyl-2,2-dimethyl-2H-chromene-3-carbaldehyde [ No CAS ]
[ 872177-02-1 ]

Reference： [1]Synlett,2009,p. 550 - 553

54
[ 107-86-8 ]
[ 650-51-1 ]
[ 72800-48-7 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 3853 - 3856

55
[ 107-86-8 ]
[ 14562-10-8 ]
8-phenyl-2,2-dimethyl-2H-chromene-3-carbaldehyde [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 2842 - 2851

56
[ 107-86-8 ]
[ 615-94-1 ]
[ 1082067-61-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With ethylenediamine diacetic acid In ethanol for 0.3h; Reflux; regioselective reaction;

Reference： [1]Location in patent: experimental part Jiménez-Alonso, Sandra; Pérez-Lomas, Antonio L.; Estévez-Braun, Ana; Martinez, Francisco Muñoz; Orellana, Haydee Chávez; Ravelo, Angel G.; Gamarro, Francisco; Castanys, Santiago; López, Matías [Journal of Medicinal Chemistry, 2008, vol. 51, # 22, p. 7132 - 7143]

57
[ 107-86-8 ]
[ 137571-73-4 ]
[ 1187462-06-1 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 5075 - 5079

58
[ 763-32-6 ]
[ 107-86-8 ]
[ 60857-05-8 ]

Yield	Reaction Conditions	Operation in experiment
48.5%	With toluene-4-sulfonic acid In water; toluene at 110 - 120℃; Dean-Stark;	1 A 0.75 L reactor equipped with a Dean-Stark-trap and a vacuum pump was charged with toluene (239 g) and p-toluene sulfonic acid (560 mg of a 65% solution in water, 2.11 mmol) and the solution was brought to 110 °C (ambient pressure). To this solution a mixture of 95.7 g(1.14 mol) prenal and 97.7 g(1.13 mol) of isoprenol was added by means of a syringe pump (0.7 mL/min). During the addition, water started to form and was removed into the Dean-Stark-trap. The heating temperature was kept at 120°C. At the end of the addition (i. e. after approximately 6 h) the temperature of the reactionmixture was 98°C. The reaction was heated for further 4 h after completion of the addition. After cooling to room temperature, 350 g of the reaction mixture (total mass of the mixture: 390 g) was distilled (bulb to bulb). The distillate (319 g) was analysed by GC. The yield of dehydro rose oxide (DHRO) was 48.5%, and the DHRO/NO ratio was 3.11 (in other words: 3.11:1). The reaction was carried out analogously with the catalysts listed in the below table.
	In water; toluene at 110 - 115℃; for 21.5h;	1 EXAMPLE 1; In a reaction vessel with a volume of 5 l and provided with stirrer, water separator, condenser and a metering pump, 2000 g of toluene and 1.5 g of NaHSO4 (as 10% strength aqueous solution) were initially introduced and 7.67 mol (660 g) of 3-methylbut-3-en-1-ol and 7.67 mol (643.5 g) of 3-methylbut-2-en-1-al were metered in over the course of 16 h at 110 to 115° C. The water was continuously removed azeotropically from the reaction mixture with toluene and the toluene was returned. The reaction mixture was then stirred for a further 5.5 h at 115° C. The resulting reaction mixture was then washed with 278 g of 2% strength NaOH solution. The toluene was distilled off at a pressure of 200 mbar over a 30 cm-long column, filled with Raschig rings. The conversion to the dehydrorose oxide (DHR) was 62.7% of theory. Finally the DHR was separated from nerol oxide and high-boiling secondary components by distillation and obtained with a purity of >99%.

Reference： [1]Current Patent Assignee: BASF SE - WO2014/184311, 2014, A1 Location in patent: Page/Page column 6; 7
[2]Current Patent Assignee: BASF SE - US2010/311988, 2010, A1 Location in patent: Page/Page column 4

59
[ 107-86-8 ]
[ 59236-37-2 ]
[ 1309354-05-9 ]
(2S*,4S*,6S*)-9-chloro-2-methyl-2,3,4,6-tetrahydro-1H-2,6-methanobenzo[c][1,5]oxazocin-4-ol [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 3136 - 3138

60
[ 107-86-8 ]
[ 84902-24-9 ]
[ 1309354-01-5 ]
(2S*,4S*,6S*)-2,10-dimethyl-2,3,4,6-tetrahydro-1H-2,6-methanobenzo[c][1,5]oxazocin-4-ol [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 3136 - 3138

61
[ 107-86-8 ]
[ 4707-32-8 ]

Reference： [1]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 153 - 156

62
[ 107-86-8 ]
[ 4707-32-8 ]
[ 4707-33-9 ]

Reference： [1]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 153 - 156

63
[ 107-86-8 ]
[ 60682-95-3 ]
[ 1380035-31-3 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 9086 - 9089

64
[ 107-86-8 ]
[ 60682-95-3 ]
[ 1380035-51-7 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 9086 - 9089

65
[ 848821-58-9 ]
[ 107-86-8 ]
C₂₅H₃₃NOSi [ No CAS ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3740 - 3743

66
[ 1677-44-7 ]
[ 107-86-8 ]
2,2,9-trimethyl-2H-pyrano[3,2-c]quinolin-5(6H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1252 - 1275

67
[ 107-86-8 ]
[ 20300-59-8 ]
[ 1616761-15-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With (S)-2-((tert-butyldimethylsilyloxy)dinaphthalen-2-ylmethyl)pyrrolidine In chloroform at 20℃; for 7h; enantioselective reaction;

Reference： [1]Song, Aiguo; Zhang, Xishuai; Song, Xixi; Chen, Xiaobei; Yu, Chenguang; Huang, He; Li, Hao; Wang, Wei [Angewandte Chemie - International Edition, 2014, vol. 53, # 19, p. 4940 - 4944][Angew. Chem., 2014, vol. 126, # 19, p. 5040 - 5044,5]

68
[ 848821-58-9 ]
[ 107-86-8 ]
C₁₆H₂₀O₅S [ No CAS ]
C₄₁H₅₃NO₆SSi [ No CAS ]

Reference： [1]Tetrahedron,2014,vol. 70,p. 4386 - 4394

69
[ 22348-32-9 ]
[ 107-86-8 ]
[ 52287-52-2 ]
N-5-(2,6-dichlorophenyl-3-methyl-6-nitrocyclohex-2-enyl)-2-diphenyl-(pyrrolidin-2yl)methanol [ No CAS ]
N-5-(2,6-dichlorophenyl-3-methyl-6-nitrocyclohex-2-enyl)-2-diphenyl-(pyrrolidin-2yl)methanol [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5267 - 5277

70
[ 22348-32-9 ]
[ 107-86-8 ]
[ 34209-97-7 ]
N-5-(2,4-dichlorophenyl-3-methyl-6-nitrocyclohex-2-enyl)-2-diphenyl(pyrrolidin-2-yl)methanol [ No CAS ]
N-5-(2,4-dichlorophenyl-3-methyl-6-nitrocyclohex-2-enyl)-2-diphenyl(pyrrolidin-2-yl)methanol [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5267 - 5277

71
[ 22348-32-9 ]
[ 107-86-8 ]
[ 15241-23-3 ]
N-(5-phenyl-3-methyl-6-nitrocyclohex-2-enyl)-2-diphenyl(pyrrolidin-2-yl)methanol [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5267 - 5277

72
[ 107-86-8 ]
[ 33143-29-2 ]

Reference： [1]Journal of Molecular Catalysis A: Chemical,2015,vol. 398,p. 11 - 16
[2]Tetrahedron,2016,vol. 72,p. 8406 - 8416

73
[ 107-86-8 ]
[ 130-15-4 ]
[ 84-54-8 ]

Yield	Reaction Conditions	Operation in experiment
78%	With benzoic acid; L-proline; In toluene; at 50℃; for 5h;Inert atmosphere;Catalytic behavior;	To toluene (5 mL) were added 1,4-naphthoquinone (1a-e),1,4-anthracene dion (1f),1,2-naphthoquinone (8) compound or A mixture (1.0 mmol) of 1,4-benzoquinone (10) alpha, beta- unsaturated aldehyde compound (2, 1.6 mmol),The catalyst is L- proline (20 mol%), and the additive is benzoic acid (10 mol%) was stirred at 50 for 5 hours. After completion of the reaction, completion of the reaction was confirmed by TLC, and the reaction mixture was evaporated in a rotary evaporator. The residue was purified by silica gel column chromatography using hexane / ethyl acetate as an eluent to obtain the desired compound.

Reference： [1]Chemical Communications,2015,vol. 51,p. 8592 - 8595
[2]Patent: KR2017/70910,2017,A .Location in patent: Paragraph 0029-0030; 0032

74
[ 107-86-8 ]
[ 475-38-7 ]
[ 14569-42-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With benzoic acid; <i>L</i>-proline In toluene at 50℃; for 5h; Inert atmosphere; Enzymatic reaction;

Reference： [1]Somai Magar, Krishna Bahadur; Xia, Likai; Lee, Yong Rok [Chemical Communications, 2015, vol. 51, # 41, p. 8592 - 8595]

75
[ 107-86-8 ]
[ 3163-07-3 ]
[ 1386351-26-3 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 11460 - 11467

76
[ 107-86-8 ]
[ 150192-39-5 ]
C₁₃H₁₈O₃ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 1777 - 1781
Angew. Chem.,2016,vol. 128,p. 1809 - 1813

77
[ 5381-20-4 ]
[ 107-86-8 ]
C₁₄H₁₄O₂S [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 1777 - 1781
Angew. Chem.,2016,vol. 128,p. 1809 - 1813

78
[ 5788-17-0 ]
[ 107-86-8 ]
4-methoxy-5-(2-methylprop-1-en-1-yl)furan-2(5H)-one [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 828 - 831

79
[ 107-86-8 ]
[ 541-47-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 4H₃N4H⁽¹⁺⁾CuMo₆O₁₈(OH)6^(4-); water; oxygen; sodium carbonate at 50℃; for 12h;
91%	With copper acetylacetonate; oxygen; sodium hydroxide; 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In water at 50℃; for 12h; Sealed tube;
38%	With Iron(III) nitrate nonahydrate; oxygen; sodium 2,2,2-trifluoroacetate In ethyl acetate at 25℃; for 16h;	Typical procedure for the oxidation reaction (Table 1, entry 14). General procedure: In a test tube, trans-2-decenal (167 mg, 1.0 mmol) was added to a suspension of Fe(NO3)3·9H2O(4.1 mg, 0.010 mmol) and CF3COONa (28 mg, 0.20 mmol) in EtOAc (0.50 mL). O2 balloon (1atm) was attached at top of the test tube, and inner atmosphere was replaced by O2. After stirring16 h at 25 °C, EtOAc (3 mL) and 1M HCl aq. (1 mL) were added and resulting biphasic mixture wasstirred for 1 min. Organic phase was separated, and water phase was extracted by EtOAc (3 mL X2). To the collected organic phase was then added measured amount of biphenyl (as an internalstandard for NMR analysis). The conversion of substrate and the yield of products weredetermined by NMR analysis (400 MHz, CDCl3, 25 °C). Products were identified by comparison tothe NMR signals of authentic samples. The same reaction was performed twice for each reaction.

Reference： [1]Yu, Han; Ru, Shi; Zhai, Yongyan; Dai, Guoyong; Han, Sheng; Wei, Yongge [ChemCatChem, 2018, vol. 10, # 6, p. 1253 - 1257]
[2]Liu, Mingxin; Li, Chao-Jun [Angewandte Chemie - International Edition, 2016, vol. 55, # 36, p. 10806 - 10810][Angew. Chem., 2016, vol. 128, p. 10964 - 10968]
[3]Tanaka, Shinji; Kon, Yoshihiro; Uesaka, Yumiko; Morioka, Ryo; Tamura, Masanori; Sato, Kazuhiko [Chemistry Letters, 2016, vol. 45, # 2, p. 188 - 190]

80
[ 107-86-8 ]
[ 35436-57-8 ]
C₁₀H₁₄O₄ [ No CAS ]
C₁₀H₁₄O₄ [ No CAS ]
C₁₀H₁₄O₄ [ No CAS ]

Reference： [1]Chemical Science,2017,vol. 8,p. 2904 - 2913

81
[ 107-86-8 ]
[ 35436-57-8 ]
C₁₄H₂₀O₅ [ No CAS ]

Reference： [1]Chemical Science,2017,vol. 8,p. 2904 - 2913

82
[ 107-86-8 ]
[ 1203507-02-1 ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 3117 - 3121

83
[ 107-86-8 ]
[ 99438-28-5 ]
[ 161973-89-3 ]
C₃₄H₆₁BO₃Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-<<2-(trimethylsilyl)ethoxy>methoxy>-1-propene With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.25h; Inert atmosphere; Schlenk technique; Stage #2: (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; cyclohexane at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #3: 3,3-dimethyl acrylaldehyde In tetrahydrofuran; cyclohexane at -100 - 20℃; Inert atmosphere; Schlenk technique;

Reference： [1]Terwilliger, Daniel W.; Trauner, Dirk [Journal of the American Chemical Society, 2018, vol. 140, # 8, p. 2748 - 2751]

84
[ 107-86-8 ]
[ 1080-12-2 ]
(1E,4E)-1-(4-hydroxy-3-methoxyphenyl)-7-methylocta-1,4,6-trien-3-one [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2018,vol. 66,p. 7983 - 7994

85
[ 763-32-6 ]
[ 107-86-8 ]
[ 556-82-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 53.06% 2: 8.78%	With 5%-palladium/activated carbon; oxygen at 80℃; for 5h;	I.10 I) Catalytic Isomerization The individual experiments were generally conducted under oxygenous atmosphere in a pressure-stable reactor with a mechanical stirrer. Performance of the catalytic isomerization on a laboratory scale was accomplished using a 350 mL glass pressure vessel (DN 50 for 8 bar), equipped with a baffle, a heating apparatus (Huber Ministat 230-CC), a sparging stirrer (Pt 100, 7 bar safety valve, gas connections with QC quick-release couplings), a pressure reducer for the pressure range of 0-10 bar, and optionally a flowmeter at the gas inlet and a pressure regulator, i.e. pressure release valve, at the gas outlet. (0121) Unless stated otherwise, the following standard conditions were used for the catalytic isomerization experiments which follow: (0122) Stirrer speed: 1000 rpm (0123) Exchange rate of oxygenous gas: 30 L/h (0124) Reaction temperature: 80° C. (0125) Pressure in the reactor: 5-20 bar (0126) Amount of feedstock: 100 g (0127) The catalytic isomerization experiments were conducted with various Pd catalysts. The results of the experiments are compiled in table 1. As apparent from table 1, carbon-supported Pd catalysts show thee desired activity. In general, total selectivities, i.e. the selectivities of prenol and prenal together, of more than 90% are attained. It was possible to successfully implement recycling of the catalyst and subsequent reuse. In addition, it was generally possible to identify a decline in the formation of isoamyl alcohol by virtue of the reaction conditions used; the values were in a range of 0.5-1.0 area %. (0129) Table 2 shows the profile of the conversion of MBE against time and the amount of prenol and prenal formed in a representative catalytic isomerization reaction.

Reference： [1]Current Patent Assignee: BASF SE - US2019/77736, 2019, A1 Location in patent: Paragraph 0119-0129

86
[ 930-88-1 ]
[ 1068-21-9 ]
[ 107-86-8 ]
diethyl [(3aSR,4RS,7aSR)-2,6-dimethyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl]phosphoramidate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With acetic anhydride; toluene-4-sulfonic acid In toluene at 110℃; diastereoselective reaction;	4.2. General procedure for the synthesis of products 6 General procedure: To a stirred solution of diethyl phosphoramidate (154 mg,1 mmol), TsOH (8.6 mg, 0.05 mmol), acetic anhydride (4.8 mL,0.05 mmol) in 3 mL of toluene was added the aldehyde (1 mmol), the maleimide (1 mmol). The solution was stirred under reflux for24 h, and then the solvent was removed under vacuum. The crude of the reaction was purified with flash chromatography to give the desired compound.

Reference： [1]Chabour, Ihssene; Nájera, Carmen; Sansano, José M. [Tetrahedron, 2020, vol. 76, # 2]

87
[ 941-69-5 ]
[ 1068-21-9 ]
[ 107-86-8 ]
diethyl [(3aSR,4RS,7aSR)-6-methyl-1,3-dioxo-2-phenyl-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl]phosphoramidate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With acetic anhydride; toluene-4-sulfonic acid In toluene at 110℃; diastereoselective reaction;	4.2. General procedure for the synthesis of products 6 General procedure: To a stirred solution of diethyl phosphoramidate (154 mg,1 mmol), TsOH (8.6 mg, 0.05 mmol), acetic anhydride (4.8 mL,0.05 mmol) in 3 mL of toluene was added the aldehyde (1 mmol), the maleimide (1 mmol). The solution was stirred under reflux for24 h, and then the solvent was removed under vacuum. The crude of the reaction was purified with flash chromatography to give the desired compound.

Reference： [1]Chabour, Ihssene; Nájera, Carmen; Sansano, José M. [Tetrahedron, 2020, vol. 76, # 2]

88
[ 107-86-8 ]
[ 42059-80-3 ]
(2-hydroxy-5-nitrophenyl)(p-tolyl)methanone [ No CAS ]

Reference： [1]Green Chemistry,2020,vol. 22,p. 4523 - 4531

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[ CAS No. 107-86-8 ] {[proInfo.proName]}

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[ 107-86-8 ] Synthesis Path-Upstream 1~4

[ 107-86-8 ] Synthesis Path-Downstream 1~88

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