2-Hexen-4-ynedioic acid dimethyl ester

Base Information

• Chemical Name: 2-Hexen-4-ynedioic acid dimethyl ester
• CAS No.: 13086-06-1
• Molecular Formula: C8H8O4
• Molecular Weight: 168.149
• Mol file: 13086-06-1.mol

Synonyms:2-Hexen-4-ynedioic acid dimethyl ester

Chemical Property of 2-Hexen-4-ynedioic acid dimethyl ester

Chemical Property:

• Melting Point: 53-54℃
• Boiling Point: 251℃
• Flash Point: 106℃
• PSA: 52.60000
• Density: 1.163
• LogP: -0.10800

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Hexen-4-ynedioic acid dimethyl ester

There total 4 articles about 2-Hexen-4-ynedioic acid dimethyl 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: 88.0%

(-)-(3S,5E)-1-benzyloxyhept-5-en-3-ol (853193-61-0) + propynoic acid methyl ester (922-67-8) → (+)-methyl (2E,5S,7E)-5-(2-benzyloxyethyl)-4-oxa-nona-2,7-dienoate (870095-89-9) + (E)-hex-2-en-4-ynedioic acid dimethyl ester (13086-06-1,54299-80-8)

Guidance literature:

With Quinuclidine; In dichloromethane; at 20 ℃; for 7h;

DOI:10.1021/ol0611705

Reference yield: 65.0%

1-hydroxy-2-(prop-1-ynyl)benzene (66022-00-2) + propynoic acid methyl ester (922-67-8) → (E)-hex-2-en-4-ynedioic acid dimethyl ester (13086-06-1,54299-80-8) + C13H12O3

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In dichloromethane; at 0 - 20 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201604531

Reference yield: 18.0%

N-(benzylidene)-p-methylbenzenesulfonamide (51608-60-7) + propynoic acid methyl ester (922-67-8) → methyl 2-(phenyl(tosylimino)methyl)acrylate (1207681-10-4) + hex-2-en-4-ynedioic acid dimethyl ester (13086-06-1)

Guidance literature:

With triphenylphosphine; In toluene; at 80 ℃; for 12h; Inert atmosphere;

DOI:10.1002/chem.200902105

upstream raw materials:

(-)-(3S,5E)-1-benzyloxyhept-5-en-3-ol

propynoic acid methyl ester

1-hydroxy-2-(prop-1-ynyl)benzene

N-(benzylidene)-p-methylbenzenesulfonamide

Refernces

• 1、 Echeverria, Pierre -Georges,Fürstner, Alois. "An Iron-Catalyzed Bond-Making/Bond-Breaking Cascade Merges Cycloisomerization and Cross-Coupling Chemistry". supporting information. p. 11188 - 11192. Retrieved 2016/10/13.
• 2、 Barry, Conor S.,Elsworth, Jon D.,Seden, Peter T.,Bushby, Nick,Harding, John R.,Alder, Roger W.,Willis, Christine L.. "Total synthesis of the marine natural product (-)-clavosolide A". . p. 3319 - 3322. Retrieved 2007/10/03.