(2Z,6Z)-3,7,11-Trimethyl-2,6,10-dodecatrienoic acid ethyl ester

Base Information

• Chemical Name: (2Z,6Z)-3,7,11-Trimethyl-2,6,10-dodecatrienoic acid ethyl ester
• CAS No.: 20085-73-8
• Molecular Formula: C17H28O2
• Molecular Weight: 264.408
• Mol file: 20085-73-8.mol

Synonyms:(2Z,6Z)-3,7,11-trimethyl-dodeca-2,6,10-trienoic acid ethyl ester;ethyl 3,7,11-trimethyldodeca-2(Z),6(Z),10-trienoate;2Z-ethyl farnesoate;ethyl farnesoate;ethyl ester of Z,Z-farnesylic acid;ethyl (Z,Z)-farnesoate;

Chemical Property of (2Z,6Z)-3,7,11-Trimethyl-2,6,10-dodecatrienoic acid ethyl ester

Chemical Property:

• PSA: 26.30000
• LogP: 4.96870

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2Z,6Z)-3,7,11-Trimethyl-2,6,10-dodecatrienoic acid ethyl ester

There total 17 articles about (2Z,6Z)-3,7,11-Trimethyl-2,6,10-dodecatrienoic acid ethyl 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: 82.0%

methylmagnesium chloride (676-58-4) + ethyl (2E,6Z)-3-[(diethoxyphosphoryl)oxy]-7,11-dimethyl-2,6,10-dodecatrienoate (477960-40-0) → ethyl (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienoate (20085-73-8)

Guidance literature:

With copper(l) iodide; methyllithium; In tetrahydrofuran; diethyl ether; at -30 ℃; for 3h;

DOI:10.1021/jo026295b

Reference yield: 64.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (Z)-nerylacetone (3879-26-3) → ethyl (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienoate (20085-73-8) + ethyl (2E,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienoate (20085-72-7)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; mineral oil; at -20 ℃; for 0.5h; Inert atmosphere;

(Z)-nerylacetone; In tetrahydrofuran; mineral oil; at -20 - 25 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ja106813s

Reference yield: 64.0%

tetramethylstannane (594-27-4) + ethyl 3-(((trifluoromethyl)sulfonyl)oxy)-7,11-dimethyldodeca-2(E),6(Z),10-trienoate (247113-11-7) → ethyl (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienoate (20085-73-8)

Guidance literature:

With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; triphenyl-arsane; In 1-methyl-pyrrolidin-2-one; at 100 ℃; for 15h;

DOI:10.1021/jo000942m

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

(Z)-nerylacetone

trimethylsilanyl-acetic acid ethyl ester

1,1-dimethoxy-4-methyl-8-oxonon-4Z-ene

Downstream raw materials:

β-cis-bergamotene

(2Z,6Z)-farnesol

2E,6Z-farnesol

Refernces

• 1、 Snyder, Scott A.,Treitler, Daniel S.,Brucks, Alexandria P.. "Simple reagents for direct halonium-induced polyene cyclizations". supporting information; experimental part. p. 14303 - 14314. Retrieved 2011/01/04.
• 2、 Brown, Richard C. D.,Bataille, Carole J.,Hughes, Robert M.,Kenney, Anne,Luker, Tim J.. "Permanganate oxidation of 1,5,9-trienes: Stereoselective synthesis of tetrahydrofuran-containing fragments". . p. 8079 - 8085. Retrieved 2007/10/03.