Dimethyl 4-oxocyclopentane-1,2-dicarboxylate

Base Information

• Chemical Name: Dimethyl 4-oxocyclopentane-1,2-dicarboxylate
• CAS No.: 6453-07-2
• Molecular Formula: C₉H₁₂O₅
• Molecular Weight: 200.191
• European Community (EC) Number: 633-210-1
• DSSTox Substance ID: DTXSID201346538
• Mol file: 6453-07-2.mol

Synonyms:6453-07-2;dimethyl 4-oxocyclopentane-1,2-dicarboxylate;4-OXO-CYCLOPENTANE-1,2-DICARBOXYLIC ACID DIMETHYL ESTER;1,2-dimethyl 4-oxocyclopentane-1,2-dicarboxylate;DIMETHYL 4-OXO-1,2-CYCLOPENTANEDICARBOXYLATE;1,2-Cyclopentanedicarboxylic acid, 4-oxo-, 1,2-diMethyl ester, (1R,2R)-;SCHEMBL994649;1,2-Cyclopentanedicarboxylic acid, 4-oxo-, dimethyl ester;GMKJWKXCHOWVDN-UHFFFAOYSA-N;DTXSID201346538;3,4-dimethoxycarbonylcyclopentanone;1,2-Cyclopentanedicarboxylic acid, 4-oxo-, 1,2-dimethyl ester;MFCD00154556;AKOS015962648;AB93371;PB27723;SB13042;1,2-di(methoxycarbonyl)-4-cyclopentanone;AS-50397;PD160215;dimethyl4-oxocyclopentane-1,2-dicarboxylate;CS-0052747;FT-0740610;P10086;rel-dimethyl (1R,2S)-4-oxocyclopentane-1,2-dicarboxylate

Chemical Property of Dimethyl 4-oxocyclopentane-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 0.00123mmHg at 25°C
• Refractive Index: 1.474
• Boiling Point: 299°C at 760 mmHg
• Flash Point: 130.6°C
• PSA: 69.67000
• Density: 1.247g/cm³
• LogP: -0.07230
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 200.06847348
• Heavy Atom Count: 14
• Complexity: 244

Purity/Quality:

99% ^*data from raw suppliers

1,2-Cyclopentanedicarboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1CC(=O)CC1C(=O)OC

Technology Process of Dimethyl 4-oxocyclopentane-1,2-dicarboxylate

There total 22 articles about Dimethyl 4-oxocyclopentane-1,2-dicarboxylate 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: 100.0%

methanol (67-56-1) + rac-4-oxocyclopentane-1,2-dicarboxylic acid (1703-61-3) → dimethyl 4-oxocyclopentane-1,2-dicarboxylate (6453-07-2)

Guidance literature:

With thionyl chloride; In methanol; at 66 ℃; for 2h;

Reference yield: 99.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + racemic trans-cyclopentanone-3,4-dicarboxylic acid (1703-61-3,3128-17-4,3128-18-5,67885-97-6) → (+/-)-trans-4-oxo-1,2-cyclopentanedicarboxylic acid bis(methyl ester) (6453-07-2,28269-02-5,28269-03-6,35079-19-7,74500-50-8,115794-30-4)

Guidance literature:

DOI:10.1016/S0040-4039(01)92968-5

Reference yield: 87.0%

rac-trans-3,4-bis(methoxycarbonyl)hexanedioic acid (16631-27-9,106529-34-4,138405-05-7) → (+/-)-trans-4-oxo-1,2-cyclopentanedicarboxylic acid bis(methyl ester) (6453-07-2,28269-02-5,28269-03-6,35079-19-7,74500-50-8,115794-30-4)

Guidance literature:

With sodium acetate; acetic anhydride; at 130 ℃; for 1h;

upstream raw materials:

methanol

rac-4-oxocyclopentane-1,2-dicarboxylic acid

diazomethane

(2S,3R)-1,2,3,4-butanetetracarboxylic acid

Downstream raw materials:

trans-(1R,2R)-1,2-Bis(methoxycarbonyl)-4-oxocyclopentane

(1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid

(+)-(1S,2S)-dimethyl-4-oxocyclopentane 1,2-dicarboxylate

2,4-Dioxo-1,3-diaza-spiro[4.4]nonane-7,8-dicarboxylic acid