Methyl 3-oxocyclopent-1-enecarboxylate

Base Information

• Chemical Name: Methyl 3-oxocyclopent-1-enecarboxylate
• CAS No.: 108384-35-6
• Molecular Formula: C₇H₈O₃
• Molecular Weight: 140.139
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID20452441
• Nikkaji Number: J652.981J
• Wikidata: Q82273081
• Mol file: 108384-35-6.mol

Synonyms:108384-35-6;METHYL 3-OXOCYCLOPENT-1-ENECARBOXYLATE;Methyl 3-oxocyclopentene-1-carboxylate;1-Cyclopentene-1-carboxylic acid, 3-oxo-, methyl ester;METHYL 3-OXOCYCLOPENT-1-ENE-1-CARBOXYLATE;1-Cyclopentene-1-carboxylicacid,3-oxo-,methylester(9CI);3-Oxo-1-cyclopentene-1-carboxylic acid methyl ester;SCHEMBL2600399;DTXSID20452441;MFCD12828194;AKOS006334744;DS-7926;CS-0150822;FT-0747522;METHYL3-OXOCYCLOPENT-1-ENECARBOXYLATE;EN300-381185;A908915

Chemical Property of Methyl 3-oxocyclopent-1-enecarboxylate

Chemical Property:

• PSA: 43.37000
• LogP: 0.44870
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 140.047344113
• Heavy Atom Count: 10
• Complexity: 203

Purity/Quality:

99% ^*data from raw suppliers

Methyl3-Oxocyclopent-1-enecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=O)CC1

Technology Process of Methyl 3-oxocyclopent-1-enecarboxylate

There total 9 articles about Methyl 3-oxocyclopent-1-enecarboxylate 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: 89.0%

3-hydroxy-cyclopentene-1-carboxylic acid methyl ester (162086-59-1) → methyl 3-oxocyclopent-1-enecarboxylate (108384-35-6)

Guidance literature:

With laccase M₁₂₀; oxygen; 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate; In aq. acetate buffer; at 30 ℃; for 24h; pH=5; Enzymatic reaction;

DOI:10.1039/c7gc02215h

Reference yield: 85.0%

tert.-butylhydroperoxide (75-91-2) + 1-(carboxymethoxy)cyclopentadiene (25662-28-6) → methyl 3-oxocyclopent-1-enecarboxylate (108384-35-6) + 1-tert-butylperoxy-cyclopent-2-enecarboxylic acid methyl ester

Guidance literature:

With potassium carbonate; 20percent Pd(OH)2/C; In dichloromethane; at 24 ℃; for 48h;

DOI:10.1021/ja0340735

Reference yield: 79.0%

1-(carboxymethoxy)cyclopentadiene (25662-28-6) → methyl 3-oxocyclopent-1-enecarboxylate (108384-35-6)

Guidance literature:

With tert.-butylhydroperoxide; Rh₂(Cap)4; potassium carbonate; In dichloromethane; for 1h;

DOI:10.1021/ja045330o

upstream raw materials:

1-(carboxymethoxy)cyclopentadiene

methyl 1-phenylsulfonyl-3-hydroxycyclopentane-1-carboxylate

tert.-butylhydroperoxide

methyl 1-phenylsulfonyl-3-cyclopentene-1-carboxylate

Downstream raw materials:

methyl 3-oxocyclopentane-1-carboxylate

(R)-methyl 3-oxocyclopentanecarboxylate

methyl (1S)-3-oxocyclopentanecarboxylate

Refernces

• 1、 Tata, Rama Rao,Harmata, Michael. "Synthesis of methyl 2-bromo-3-oxocyclopent-1-ene-1-carboxylate". . p. 425 - 438. Retrieved 2019/08/20.
• 2、 Brenna, Elisabetta,Crotti, Michele,Gatti, Francesco G.,Monti, Daniela,Parmeggiani, Fabio,Pugliese, Andrea,Tentori, Francesca. "Biocatalytic synthesis of chiral cyclic γ-oxoesters by sequential C-H hydroxylation, alcohol oxidation and alkene reduction". supporting information. p. 5122 - 5130. Retrieved 2017/11/09.