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

Base Information

• Chemical Name: (2E,6Z)-3,7,11-Trimethyl-2,6,10-dodecatrienoic acid methyl ester
• CAS No.: 4176-79-8
• Molecular Formula: C16H26O2
• Molecular Weight: 250.381
• Mol file: 4176-79-8.mol

Synonyms:(2E,6Z)-3,7,11-Trimethyl-2,6,10-dodecatrienoic acid methyl ester;Methyl trans,cis-farnesate

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

Chemical Property:

• PSA: 26.30000
• LogP: 4.57860

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 5 articles about (2E,6Z)-3,7,11-Trimethyl-2,6,10-dodecatrienoic 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: 80.0%

methyl (2E,6Z)-3-[(diethoxyphosphoryl)oxy]-7,11-dimethyl-2,6,10-dodecatrienoate (1228187-19-6) + methyllithium (917-54-4) → methyl (2Z,6Z)-farnesenate (4176-78-7) + methyl (2E,6Z)-farnesoate (4176-79-8)

Guidance literature:

methyllithium; With copper(l) iodide; In tetrahydrofuran; diethyl ether; at 0 ℃;

With methylmagnesium chloride; In tetrahydrofuran; diethyl ether; at -35 ℃;

methyl (2E,6Z)-3-[(diethoxyphosphoryl)oxy]-7,11-dimethyl-2,6,10-dodecatrienoate; In tetrahydrofuran; at -35 ℃; for 1.5h; optical yield given as %de;

DOI:10.1021/ol100513y

Reference yield: 52.0%

(Z)-nerylacetone (3879-26-3) + trimethyl phosphonoacetate (5927-18-4) → methyl (2Z,6Z)-farnesenate (4176-78-7) + methyl (2E,6Z)-farnesoate (4176-79-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1021/tx9601162

Reference yield:

(Z)-nerylacetone (3879-26-3) → methyl (2Z,6Z)-farnesenate (4176-78-7) + methyl (2E,6Z)-farnesoate (4176-79-8)

Guidance literature:

With diethyl ether; Erwaermen des nach der Hydrolyse erhaltenen Reaktionsprodukts mit wss.Schwefelsaeure in Methanol;

DOI:10.1039/j39660002144

upstream raw materials:

(Z)-nerylacetone

trimethyl phosphonoacetate

methyl (2E,6Z)-3-[(diethoxyphosphoryl)oxy]-7,11-dimethyl-2,6,10-dodecatrienoate

methyllithium

Downstream raw materials:

Methyl (2E)-6,7,10,11-diepoxy-3,7,11-trimethyldodec-2-enoate

methyl (2E)-6,7-epoxyfarnesoate

methyl (2E,6Z)-10,11-epoxyfarnesoate