(E)-Ethyl 4-oxopent-2-enoate

Base Information

• Chemical Name: (E)-Ethyl 4-oxopent-2-enoate
• CAS No.: 6742-53-6
• Molecular Formula: C7H10 O3
• Molecular Weight: 142.155
• Hs Code.: 2918300090
• European Community (EC) Number: 600-220-2
• DSSTox Substance ID: DTXSID301307080
• Nikkaji Number: J1.019.367B,J1.724.371C
• ChEMBL ID: CHEMBL4559670
• Mol file: 6742-53-6.mol

Synonyms:ethylacetylacrylate

Chemical Property of (E)-Ethyl 4-oxopent-2-enoate

Chemical Property:

• Vapor Pressure: 0.000903mmHg at 25°C
• Boiling Point: 282.1°C at 760 mmHg
• Flash Point: 138.6°C
• PSA: 43.37000
• LogP: 0.69470
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 142.062994177
• Heavy Atom Count: 10
• Complexity: 158

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC(=O)C
• Isomeric SMILES: CCOC(=O)/C=C/C(=O)C

Technology Process of (E)-Ethyl 4-oxopent-2-enoate

There total 41 articles about (E)-Ethyl 4-oxopent-2-enoate 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: 91.0%

ethyl 2-diazo-4-oxopentanoate (1341127-67-0) → (E)-ethyl 4-oxo-2-pentenoate (6742-53-6,10150-93-3,200628-30-4)

Guidance literature:

With tetrakis(acetonitrile)copper(I)tetrafluoroborate; In dichloromethane; at 20 ℃; for 2h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ja208965b

Reference yield: 82.0%

ethyl 2-hydroxyacetate (623-50-7) + 1-triphenylphosphoranylidene-2-propanone (1439-36-7) → (E)-ethyl 4-oxo-2-pentenoate (6742-53-6,10150-93-3,200628-30-4)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 23 ℃; for 30h; Inert atmosphere;

DOI:10.1021/ja501005g

Reference yield: 80.0%

ethyl (triphenylphosphoranylidene)acetate (1099-45-2) + 2-oxopropanal (78-98-8) → (E)-ethyl 4-oxo-2-pentenoate (6742-53-6,10150-93-3,200628-30-4) + (Z)-ethyl 4-oxopent-2-enoate (200628-30-4)

Guidance literature:

In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 20h;

DOI:10.1016/j.ejmech.2013.10.026

upstream raw materials:

4-oxopentanoic acid ethyl ester

2-oxo-but-3-ene-1,1,4t-tricarboxylic acid triethyl ester

4-hydroxy-pent-2-enoic acid ethyl ester

Ethyl 3(R,S)-benzoyloxy-4-oxopentanoate

Downstream raw materials:

(1S,6S)-6-Acetyl-3-methyl-cyclohex-3-enecarboxylic acid ethyl ester

(+/-)-trans-6-acetyl-cyclohex-3-enecarboxylic acid

5-hydroxy-5-methyl-isoxazolidine-2,3-dicarboxylic acid 2-benzyl ester 3-ethyl ester

(3S,4S)-ethyl 3-benzyl-6-methyl-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate

Refernces

• 1、 Johansson, Henrik,Hussain, Omar,Allison, Simon J.,Robinson, Tony V.,Phillips, Roger M.,Sejer Pedersen, Daniel. "Revisiting Bromohexitols as a Novel Class of Microenvironment-Activated Prodrugs for Cancer Therapy". supporting information. p. 228 - 235. Retrieved 2019/12/11.
• 2、 Ren, Jinfeng,Xu, Jian,Zhang, Guoning,Xu, Changliang,Zhao, LiLi,You, XueFu,Wang, Yucheng,Lu, Yu,Yu, Liyan,Wang, Juxian. "Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents". . p. 539 - 543. Retrieved 2019/01/09.