(S)-2-methyl-6-keto-(4-methyl-3-cyclohexen-1-yl)-2-hexene

Base Information

• Chemical Name: (S)-2-methyl-6-keto-(4-methyl-3-cyclohexen-1-yl)-2-hexene
• CAS No.: 170080-86-1
• Molecular Formula: C₁₄H₂₂O
• Molecular Weight: 206.328
• Mol file: 170080-86-1.mol

Synonyms:(S)-2-methyl-6-keto-(4-methyl-3-cyclohexen-1-yl)-2-hexene

Chemical Property of (S)-2-methyl-6-keto-(4-methyl-3-cyclohexen-1-yl)-2-hexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-methyl-6-keto-(4-methyl-3-cyclohexen-1-yl)-2-hexene

There total 8 articles about (S)-2-methyl-6-keto-(4-methyl-3-cyclohexen-1-yl)-2-hexene 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: 47.0%

2-methylpent-2-en-5-yl lithium (64504-53-6) + (S)-4-methyl-3-cyclohexene-1-carboxylic acid (102208-60-6) → (S)-2-methyl-6-keto-(4-methyl-3-cyclohexen-1-yl)-2-hexene (170080-86-1)

Guidance literature:

With cerium(III) chloride; In tetrahydrofuran; at -78 ℃; for 0.583333h;

DOI:10.1080/00397919508011421

Reference yield:

5-Methyl-1-(4-methylene-cyclohexyl)-hex-4-en-1-one (82096-15-9) → 1-methylene-4-(6-methylhepta-1,5-dien-2-yl)cyclohexane + (S)-2-methyl-6-keto-(4-methyl-3-cyclohexen-1-yl)-2-hexene (170080-86-1)

Guidance literature:

With borane-ammonia complex; C₁₇H₃₁Cl₂CoN₂P; In ethanol; at -15 ℃; for 24h; Overall yield = 92 percent; Overall yield = 46.9 mg; enantioselective reaction; Sealed tube; Inert atmosphere;

DOI:10.1021/jacs.1c11343

Reference yield:

C15H24O3 → 1-methylene-4-(6-methylhepta-1,5-dien-2-yl)cyclohexane + (S)-2-methyl-6-keto-(4-methyl-3-cyclohexen-1-yl)-2-hexene (170080-86-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / water; acetone / 3 h / Reflux

2.1: potassium tert-butylate / diethyl ether / 1 h / 20 °C

2.2: 20 °C

3.1: borane-ammonia complex; C₁₇H₃₁Cl₂CoN₂P / ethanol / 24 h / -15 °C / Sealed tube; Inert atmosphere

With hydrogenchloride; borane-ammonia complex; potassium tert-butylate; C₁₇H₃₁Cl₂CoN₂P; In diethyl ether; ethanol; water; acetone;

DOI:10.1021/jacs.1c11343

upstream raw materials:

4-methyl-3-pentenylmagnesium bromide

(S)-4-methyl-3-cyclohexene-1-carbonyl chloride

2-methylpent-2-en-5-yl lithium

(S)-4-methyl-3-cyclohexene-1-carboxylic acid

Downstream raw materials:

(S)-1-methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene

Refernces

• 1、 Lan, Yu,Liu, Qiang,Liu, Shihan,Liu, Xufang,Rong, Xianle. "Cobalt-Catalyzed Desymmetric Isomerization of Exocyclic Olefins". . p. 20633 - 20639. Retrieved 2021/12/17.