(Z)-diethyl pent-2-enedioate

Base Information

• Chemical Name: (Z)-diethyl pent-2-enedioate
• CAS No.: 73192-75-3
• Molecular Formula: C₉H₁₄O₄
• Molecular Weight: 186.208
• Mol file: 73192-75-3.mol

Synonyms:(Z)-diethyl pent-2-enedioate

Chemical Property of (Z)-diethyl pent-2-enedioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (Z)-diethyl pent-2-enedioate

There total 5 articles about (Z)-diethyl pent-2-enedioate 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:

diazoacetic acid ethyl ester (623-73-4) + ethyl acrylate (140-88-5,9003-32-1) → (Z)-diethyl pent-2-enedioate (73192-75-3) + (E)-diethyl glutaconate (73178-43-5) + diethyl (cis,trans)-1,2-cyclopropanedicarboxylate (20561-09-5)

Guidance literature:

molybdenum hexacarbonyl; at 65 ℃; Yield given. Further byproducts given. Yields of byproduct given;

DOI:10.1021/jo01296a047

Reference yield:

ethanol (64-17-5) + glutaconic acid (1724-02-3) → (Z)-diethyl pent-2-enedioate (73192-75-3) + (E)-diethyl glutaconate (73178-43-5)

Guidance literature:

With sulfuric acid; In ethanol; optical yield given as %de; Reflux;

DOI:10.1021/ja902458m

Reference yield:

ethanol (64-17-5) + ethyl 2,3-butadienoate (14369-81-4) + carbon monoxide (201230-82-2) → (Z)-diethyl pent-2-enedioate (73192-75-3) + (E)-diethyl glutaconate (73178-43-5)

Guidance literature:

With p-toluenesulfonic acid monohydrate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 110 ℃; for 20h; under 30003 Torr; Overall yield = 65 %; Overall yield = 120.4 mg; regioselective reaction; Autoclave; Inert atmosphere;

DOI:10.1021/jacs.5b04052

upstream raw materials:

diethyl 3-hydroxyglutarate

acetic anhydride

diazoacetic acid ethyl ester

ethyl acrylate

Downstream raw materials:

(E)-diethyl glutaconate

1,3-diethyl 2-aminoglutarate

1,3-diethyl 2-benzylaminoglutarate

diethyl (2E)-3-(3-chlorophenyl)-2-pentenedioate

Refernces

• 1、 Gioia, Claudio,Fini, Francesco,Mazzanti, Andrea,Bernardi, Luca,Ricci, Alfredo. "Organocatalytic asymmetric formal [3 + 2] cycloaddition with in situ-generated N-carbamoyl nitrones". supporting information; experimental part. p. 9614 - 9615. Retrieved 2011/02/23.