(2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid methyl ester

Base Information

Chemical Name:(2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid methyl ester
CAS No.:139694-48-7
Molecular Formula:C₁₉H₂₈O₂
Molecular Weight:288.43
Hs Code.:

Synonyms:(2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid methyl ester

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Chemical Property of (2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid methyl ester

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Technology Process of (2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid methyl ester

There total 14 articles about (2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

: 72946-10-2
diisopropyl (methoxycarbonylmethyl)phosphonate

: 139694-47-6
(E)-3-((1S,4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohex-1-yl)but-2-enal

: 139694-48-7
(2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid methyl ester

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; -78 to 0 deg C;
DOI:10.1016/S0040-4039(00)77678-7

Reference yield:

: 70224-50-9
(1S,3R,4R)-1-Acetyl-3-isopropenyl-4-methyl-4-vinylcyclohexane

: 139694-48-7
(2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / tetrahydrofuran / 1.5 h / 0 °C

2: 67 percent / PCC, Celite 545 / CH₂Cl₂ / 17 h / Ambient temperature

3: 86 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) 40 min

With Celite; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

Reference yield:

: 139694-38-5
2-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-2-methyl-[1,3]dioxolane

: 139694-48-7
(2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 93 percent / 80percent AcOH / 26 °C

2: Zn / various solvent(s) / 40 °C / ultrasonic irradiation

3: PhNMe₂ / CHCl₃ / 60 °C

4: DBU / benzene / 80 °C

5: DIBAL / CH₂Cl₂ / -78 °C

6: PDC, 4A MS / CH₂Cl₂ / 26 °C

7: 95 percent / t-BuOK / tetrahydrofuran / -78 to 0 deg C

With dipyridinium dichromate; potassium tert-butylate; diisobutylaluminium hydride; acetic acid; N,N-dimethyl-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc; In tetrahydrofuran; dichloromethane; chloroform; benzene;
DOI:10.1016/S0040-4039(00)77678-7