2-Hexen-4-ynedioic acid, dimethyl ester, (2E)-

Base Information

• Chemical Name: 2-Hexen-4-ynedioic acid, dimethyl ester, (2E)-
• CAS No.: 54299-80-8
• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.149
• Mol file: 54299-80-8.mol

Synonyms:dimethyl (E)-hex-2-en-4-yne dioate;dimethyl trans-but-1-en-3-yne-1,4-dicarboxylate;dimethyl (E)-hex-2-en-4-yne-1,6-dioate;2-hexen-4-ynedioic acid dimethyl ester;dimethyl but-1-en-3-yne-1,4-dicarboxylate;Dimethyl (E)-1-buten-3-yne-1,4-dicarboxylate;2-Hexen-4-ynedioic acid,dimethyl ester,(2E);(E)-MeO2CCHCHCCCO2Me;

Chemical Property of 2-Hexen-4-ynedioic acid, dimethyl ester, (2E)-

Chemical Property:

• Melting Point: 52 °C (petroleum ether)
• Boiling Point: 250.9±32.0 °C(Predicted)
• PSA: 52.60000
• Density: 1.163±0.06 g/cm3(Predicted)
• LogP: -0.10800

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Hexen-4-ynedioic acid, dimethyl ester, (2E)-

There total 3 articles about 2-Hexen-4-ynedioic acid, dimethyl ester, (2E)- 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:

(Z)-1,1,1-trifluoro-4-iodo-2-methyl-4-phenylbut-3-en-2-ol + propynoic acid methyl ester (922-67-8) → (E)-hex-2-en-4-ynedioic acid dimethyl ester (13086-06-1,54299-80-8) + methyl (E)-3-(((Z)-1,1,1-trifluoro-4-iodo-2-methyl-4-phenylbut-3-en-2-yl)oxy)acrylate

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In dichloromethane; at 20 ℃; for 1h; Overall yield = 84 percent; Overall yield = 314 mg; Inert atmosphere;

DOI:10.1002/anie.202015232

upstream raw materials:

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

propynoic acid methyl ester

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

Downstream raw materials:

C₂₂H₂₃NO₄

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.