(1R,14S,2E,6E,10E)-1-[[(2α-Isopropyl-5β-methylcyclohexyl)oxy]acetoxy]-14β-isopropenyl-3,7,11-trimethylcyclotetradeca-2,6,10-triene

Base Information

• Chemical Name: (1R,14S,2E,6E,10E)-1-[[(2α-Isopropyl-5β-methylcyclohexyl)oxy]acetoxy]-14β-isopropenyl-3,7,11-trimethylcyclotetradeca-2,6,10-triene
• CAS No.: 72690-76-7
• Molecular Formula: C32H52O3
• Molecular Weight: 484.763
• Mol file: 72690-76-7.mol

Synonyms:(1R,14S,2E,6E,10E)-1-[[(2α-Isopropyl-5β-methylcyclohexyl)oxy]acetoxy]-14β-isopropenyl-3,7,11-trimethylcyclotetradeca-2,6,10-triene;trans-2-Menthoxyacetyloxyneocembrene

Chemical Property of (1R,14S,2E,6E,10E)-1-[[(2α-Isopropyl-5β-methylcyclohexyl)oxy]acetoxy]-14β-isopropenyl-3,7,11-trimethylcyclotetradeca-2,6,10-triene

Chemical Property:

• PSA: 35.53000
• LogP: 8.76100

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,14S,2E,6E,10E)-1-[[(2α-Isopropyl-5β-methylcyclohexyl)oxy]acetoxy]-14β-isopropenyl-3,7,11-trimethylcyclotetradeca-2,6,10-triene

There total 2 articles about (1R,14S,2E,6E,10E)-1-[[(2α-Isopropyl-5β-methylcyclohexyl)oxy]acetoxy]-14β-isopropenyl-3,7,11-trimethylcyclotetradeca-2,6,10-triene 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:

L-menthoxyacetyl chloride (15356-62-4) + (2E,6E,10E)-(1R,14S)-14-Isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienol (59686-17-8) → ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (2E,6E,10E)-(1R,14S)-14-isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienyl ester (72690-76-7)

Guidance literature:

With pyridine; In benzene; Yield given; 1.) 2 h, ice cooling, 2.) r.t.;

DOI:10.1021/jo01294a041

Reference yield:

(–)-menthyloxyacetic acid chloride (87637-47-6) + (2E,6E,10Z)-14-Isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienone (72623-61-1) → ((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (2E,6E,10Z)-(1R,14S)-14-isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienyl ester (72638-68-7,72690-76-7,87584-22-3)

Guidance literature:

With pyridine; (+)-Darvon-LiAlH₄; Multistep reaction; 1.) 0 deg C; 2.) benzene, 12 h, r.t.;

DOI:10.1246/cl.1983.1121

Reference yield: 54.0%

((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (2E,6E,10Z)-(1R,14S)-14-isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienyl ester (72638-68-7,72690-76-7,87584-22-3) → (-)-neocembrene (cembrene-A) (31570-39-5,38748-84-4,57918-06-6,71213-92-8,72690-72-3,72690-73-4,72691-72-6,73246-00-1,105662-19-9,139492-81-2)

Guidance literature:

With lithium; ethylamine; at -78 ℃;

DOI:10.1246/cl.1983.1121

upstream raw materials:

L-menthoxyacetyl chloride

(2E,6E,10E)-(1R,14S)-14-Isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienol

(–)-menthyloxyacetic acid chloride

(2E,6E,10Z)-14-Isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienone

Downstream raw materials:

(–)-(R)-cembrene A

(-)-neocembrene (cembrene-A)

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