1-Cyclopentene-1-carboxylic acid, 5-oxo-, ethyl ester

Base Information

• Chemical Name: 1-Cyclopentene-1-carboxylic acid, 5-oxo-, ethyl ester
• CAS No.: 57020-97-0
• Molecular Formula: C8H10O3
• Molecular Weight: 154.166
• DSSTox Substance ID: DTXSID30460431
• Nikkaji Number: J886.318K
• Wikidata: Q82284479
• Mol file: 57020-97-0.mol

Synonyms:57020-97-0;1-Cyclopentene-1-carboxylic acid, 5-oxo-, ethyl ester;5-oxo-cyclopentene-1-carboxylic acid ethyl ester;SCHEMBL5338308;DTXSID30460431;ethyl 5-oxo-1-cyclopentene-1-carboxylate

Chemical Property of 1-Cyclopentene-1-carboxylic acid, 5-oxo-, ethyl ester

Chemical Property:

• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 154.062994177
• Heavy Atom Count: 11
• Complexity: 215

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1=CCCC1=O

Technology Process of 1-Cyclopentene-1-carboxylic acid, 5-oxo-, ethyl ester

There total 3 articles about 1-Cyclopentene-1-carboxylic acid, 5-oxo-, ethyl ester 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: 40.0%

1,2,3-trimethoxybenzene (621-23-8) + 2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → ethyl 2-oxo-5-(2,4,6-trimethoxyphenyl)cyclopentanecarboxylate + ethyl 5-oxo-2-(2,4,6-trimethoxyphenyl)cyclopent-1-enecarboxylate (1407168-35-7) + ethyl 5-oxocyclopent-1-en-1-carboxylate (57020-97-0)

Guidance literature:

With oxygen; palladium diacetate; trifluoroacetic acid; In 1,2-dichloro-ethane; at 25 ℃; for 5h; under 760.051 Torr; Reagent/catalyst; Solvent; Time; Temperature; regioselective reaction; Catalytic behavior; Sealed tube;

DOI:10.1002/chem.201201988

Reference yield:

1-methylindole (603-76-9) + 2-ethoxycarbonyl-1-cyclopentanone (611-10-9) + phenylboronic acid (98-80-6) → 1-methyl-2-phenyl-1H-indole (3558-24-5) + ethyl 2-(1-methyl-2-phenyl-1H-indol-3-yl)-5-oxocyclopentanecarboxylate + C17H19NO3 + ethyl 5-oxocyclopent-1-en-1-carboxylate (57020-97-0)

Guidance literature:

With tert-Butyl peroxybenzoate; palladium(II) trifluoroacetate; acetic acid; In 1,4-dioxane-d8; at 26.84 ℃; Kinetics; Inert atmosphere;

DOI:10.1002/anie.201300833

Reference yield:

1-methylindole (603-76-9) + 1-methyl-2-phenyl-1H-indole (3558-24-5) + 2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → ethyl 2-(1-methyl-2-phenyl-1H-indol-3-yl)-5-oxocyclopentanecarboxylate + C17H19NO3 + ethyl 5-oxocyclopent-1-en-1-carboxylate (57020-97-0)

Guidance literature:

With tert-Butyl peroxybenzoate; palladium(II) trifluoroacetate; acetic acid; In 1,4-dioxane-d8; at 26.84 ℃; Kinetics; Inert atmosphere;

DOI:10.1002/anie.201300833

upstream raw materials:

1,2,3-trimethoxybenzene

2-ethoxycarbonyl-1-cyclopentanone

1-methylindole

phenylboronic acid

Downstream raw materials:

(3-oxo-cyclopentyl)-acetic acid

1-methyl-2-phenyl-1H-indole

(5S)-ethyl 2-oxo-5-((R)-5-oxo-2,5-dihydrofuran-2-yl)cyclopentanecarboxylate

ethyl 2-oxo-5-(5-oxo-2,5-dihydrofuran-2-yl)cyclopentanecarboxylate