4-(Benzyloxy)-4-oxobut-2-enoate

Base Information

• Chemical Name: 4-(Benzyloxy)-4-oxobut-2-enoate
• CAS No.: 538-64-7
• Molecular Formula: C18H16 O4
• Molecular Weight: 296.323
• Hs Code.: 2917190090
• DSSTox Substance ID: DTXSID40697812
• Mol file: 538-64-7.mol

Synonyms:Benzylfumarate;DTXSID40697812;4-(Benzyloxy)-4-oxobut-2-enoate

Chemical Property of 4-(Benzyloxy)-4-oxobut-2-enoate

Chemical Property:

• Vapor Pressure: 2.74E-07mmHg at 25°C
• Melting Point: 58.5-59.5°
• Refractive Index: 1.5400 (estimate)
• Boiling Point: 420.8°Cat760mmHg
• Flash Point: 209.1°C
• PSA: 52.60000
• Density: 1.187g/cm³
• LogP: 3.02940
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 205.05008376
• Heavy Atom Count: 15
• Complexity: 246

Purity/Quality:

98%,99%, ^*data from raw suppliers

BENZYL FUMARATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C=CC(=O)[O-]
• Uses: In room spray deodorant: Kulka, US 3077457 (1963 to Fritzsche Bros.).

Technology Process of 4-(Benzyloxy)-4-oxobut-2-enoate

There total 15 articles about 4-(Benzyloxy)-4-oxobut-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: 99.0%

dibenzyl maleate (622-06-0) → dibenzyl fumarate (538-64-7)

Guidance literature:

With C₁₆H₂₅N₃O₂S; In acetonitrile; at 80 ℃; for 16h; Reagent/catalyst;

DOI:10.1021/acs.joc.0c02316

Reference yield: 96.0%

(2E)-but-2-enedioic acid (110-17-8,26099-09-2) + benzyl alcohol (100-51-6,185532-71-2) → dibenzyl fumarate (538-64-7)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 24h; Reflux;

DOI:10.1016/j.ejmech.2018.07.012

Reference yield: 79.0%

benzyl diazoacetate (52267-51-3) → dibenzyl maleate (622-06-0) + dibenzyl fumarate (538-64-7)

Guidance literature:

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃;

DOI:10.1002/chem.200601692

upstream raw materials:

dibenzyl maleate

maleic acid

benzyl alcohol

(2E)-but-2-enedioic acid

Refernces

• 1、 Chang, Yejin,Cao, Min,Chan, Jessica Z.,Zhao, Cunyuan,Wang, Yuankai,Yang, Rose,Wasa, Masayuki. "Enantioselective Synthesis of N-Alkylamines through β-Amino C-H Functionalization Promoted by Cooperative Actions of B(C6F5)3and a Chiral Lewis Acid Co-Catalyst". supporting information. p. 2441 - 2455. Retrieved 2021/02/16.
• 2、 Fey, Philipp,Chartomatsidou, Roula,Kiefer, Werner,Mottram, Jeremy C.,Kersten, Christian,Schirmeister, Tanja. "New aziridine-based inhibitors of cathepsin L-like cysteine proteases with selectivity for the Leishmania cysteine protease LmCPB2.8". . p. 587 - 597. Retrieved 2018/07/25.