2-Decen-4-ynoic acid, methyl ester, (Z)-

Base Information

• Chemical Name: 2-Decen-4-ynoic acid, methyl ester, (Z)-
• CAS No.: 118793-68-3
• Molecular Formula: C11H16O2
• Molecular Weight: 180.247
• Mol file: 118793-68-3.mol

Synonyms:

Chemical Property of 2-Decen-4-ynoic acid, methyl ester, (Z)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Decen-4-ynoic acid, methyl ester, (Z)-

There total 8 articles about 2-Decen-4-ynoic acid, methyl ester, (Z)- 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: 68.0%

oct-2-ynal (1846-68-0) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → methyl (E)-dec-2-en-4-ynoate (118793-68-3,94133-53-6)

Guidance literature:

In dichloromethane; for 3h; Reflux;

DOI:10.1002/adsc.201900177

Reference yield: 50.0%

1-Heptyne (628-71-7) + (E)-methyl 3-iodoacrylate (6213-88-3) → methyl (E)-dec-2-en-4-ynoate (118793-68-3,94133-53-6)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; triethylamine; at 4 ℃; for 20h; Inert atmosphere;

DOI:10.1016/j.tet.2015.06.051

Reference yield: 29.0%

1-iodo-hept-1-yne (54573-13-6) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl (E)-dec-2-en-4-ynoate (118793-68-3,94133-53-6)

Guidance literature:

acrylic acid methyl ester; With tetrabutyl-ammonium chloride; palladium diacetate; potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h; Inert atmosphere;

1-iodo-hept-1-yne; In N,N-dimethyl-formamide; at 20 ℃; for 4.5h; Inert atmosphere;

DOI:10.1016/j.tet.2011.12.064

upstream raw materials:

diazomethane

(E)-dec-2-en-4-ynoic acid

methanol

1,1-Difluoro-dec-1-en-4-yn-3-ol

Downstream raw materials:

methyl (2E,4Z)-deca-2,4-dienoate

methyl (2Z,4Z)-2,4-decadienoate

methyl (2Z,4E)-2,4-decadienoate

methyl (2E,4E)-decadienoate

Refernces

• 1、 Mori, Kenji. "Pheromone synthesis. Part 257: Synthesis of methyl (2E,4Z,7Z)-2,4,7-decatrienoate and methyl (E)-2,4,5-tetradecatrienoate, the pheromone components of the male dried bean beetle, Acanthoscelides obtectus (Say)". supporting information. p. 5589 - 5596. Retrieved 2015/08/03.
• 2、 Tellier, Frederique,Sauvetre, Raymond. "Straightforward synthesis of α,β-unsaturated acids and derivatives". . p. 5433 - 5436. Retrieved 2007/10/02.