cis-Tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione

Base Information

• Chemical Name: cis-Tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione
• CAS No.: 35878-28-5
• Molecular Formula: C₇H₈O₃
• Molecular Weight: 140.139
• Hs Code.: 2932999099
• European Community (EC) Number: 252-773-0
• Nikkaji Number: J319.554F
• Mol file: 35878-28-5.mol

Synonyms:35878-28-5;cis-1,2-Cyclopentanedicarboxylic anhydride;cis-Tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione;MFCD01311171;cis-Cyclopentane-1,2-dicarboxylic acid anhydride;(3aS,6aR)-4,5,6,6a-tetrahydro-3aH-cyclopenta[c]furan-1,3-dione;EINECS 252-773-0;cis-Tetrahydro-1H-cyclopenta(c)furan-1,3(4H)-dione;(3aR,6aS)-hexahydro-1H-cyclopenta[c]furan-1,3-dione;Cis-tetrahydro-1H-cyclopenta[c]furan-1,3(4H)-dione;SCHEMBL4464324;NMSRALOLNIBERV-SYDPRGILSA-N;(3aR,6aS)-4,5,6,6a-Tetrahydro-3aH-cyclopenta[c]furan-1,3-dione;1H-Cyclopenta[c]furan-1,3(3aH)-dione, tetrahydro-, (3aR,6aS)-rel-;AKOS006277883;AT11428;FS-4035;cis-1,2-Cyclopentanedicarboxylicanhydride;cis-Cyclopentane-1,2-dicarboxylic anhydride;CS-0215478;EN300-252405;Cyclopentane-1alpha,2alpha-dicarboxylic anhydride;A823016;cis-1,2-Cyclopentanedicarboxylic anhydride, >=97.0% (GC);Rac-(3ar,6as)-hexahydro-1h-cyclopenta[c]furan-1,3-dione, cis

Chemical Property of cis-Tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione

Chemical Property:

• Melting Point: 73-74 °C
• Refractive Index: 1.555
• Boiling Point: 289.184 °C at 760 mmHg
• Flash Point: 140.371 °C
• PSA: 43.37000
• Density: 1.31 g/cm³
• LogP: 0.48610
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 140.047344113
• Heavy Atom Count: 10
• Complexity: 177

Purity/Quality:

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

cis-1,2-Cyclopentanedicarboxylic anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC2C(C1)C(=O)OC2=O
• Isomeric SMILES: C1C[C@@H]2[C@H](C1)C(=O)OC2=O
• Uses: cis-1,2-Cyclopentanedicarboxylic Anhydride functions as a reagent in the enantioselective synthesis of disubstituted proline derivatives and its application in synthesis of hepatitis C virus protease inhibitor telaprevir, Nrf2-Keap1 complex inhibitors preparation, binding mode and structural-activity relationship.

Technology Process of cis-Tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione

There total 10 articles about cis-Tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione 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%

cis-1,2-cyclopentanedicarboxylic acid (1461-96-7) → cyclopentane-cis-1,2-dicarboxylic acid anhydride (35878-28-5,743438-34-8)

Guidance literature:

With acetic anhydride; for 20h; Reflux;

Reference yield:

ethyl 2-oxocyclohexane carboxylate (1655-07-8) → cyclopentane-cis-1,2-dicarboxylic acid anhydride (35878-28-5,743438-34-8)

Guidance literature:

Multi-step reaction with 3 steps

1: Br₂ / CH₂Cl₂

2: aq. KOH; aq. HCl

3: AcOAc

With hydrogenchloride; potassium hydroxide; bromine; acetic anhydride; In dichloromethane;

DOI:10.1021/ja0055920

Reference yield:

(trans)-1,2-cyclopentanedicarboxylic acid (21917-20-4) → cyclopentane-cis-1,2-dicarboxylic acid anhydride (35878-28-5,743438-34-8)

Guidance literature:

With acetic anhydride;

upstream raw materials:

cis-1,2-cyclopentanedicarboxylic acid

trans-DL-1,2-cyclopentanedicarboxylic acid

trans-1,2-cyclopentanedicarboxylic acid

diethyl cyclopentane-1,2-dicarboxylate

Downstream raw materials:

cis-1,2-bis(hydroxymethyl)cyclopentane

(1S,2R)-cis-2-methoxycarbonyl-cyclopentane-1-carboxylic acid

(1R,2S)-cis-2-methoxycarbonyl-cyclopentane-1-carboxylic acid

cis-1,2-cyclopentanedicarboxylic acid

Refernces

• 1、 Zhao, Gang,Souers, Andrew J.,Voorbach, Martin,Falls, H. Doug,Droz, Brian,Brodjian, Sevan,Yau, Yi Lau,Iyengar, Rajesh R.,Gao, Ju,Judd, Andrew S.,Wagaw, Seble H.,Ravn, Matthew M.,Engstrom, Kenneth M.,Lynch, John K.,Mulhern, Mathew M.,Freeman, Jennifer,Dayton, Brian D.,Wang, Xiaojun,Grihalde, Nelson,Fry, Dennis,Beno, David W. A.,Marsh, Kennan C.,Su,Diaz, Gilbert J.,Collins, Christine A.,Sham, Hing,Reilly, Regina M.,Brune, Michael E.,Kym, Philip R.. "Validation of diacyl glycerolacyltransferase I as a novel target for the treatment of obesity and dyslipidemia using a potent and selective small molecule inhibitor". . p. 380 - 383. Retrieved 2008/09/17.
• 2、 Mittendorf, Joachim,Kunisch, Franz,Matzke, Michael,Militzer, Hans-Christian,Schmidt, Axel,Schoenfeld, Wolfgang. "Novel antifungal β-amino acids: Synthesis and activity against Candida albicans". . p. 433 - 436. Retrieved 2007/10/03.