Cyclopent-3-ene-1,1-dicarboxylic acid

Base Information

• Chemical Name: Cyclopent-3-ene-1,1-dicarboxylic acid
• CAS No.: 88326-51-6
• Molecular Formula: C7H8 O4
• Molecular Weight: 156.138
• Hs Code.: 2917209090
• NSC Number: 120465
• DSSTox Substance ID: DTXSID30298074
• Nikkaji Number: J2.400.403A
• Wikidata: Q82039667
• Mol file: 88326-51-6.mol

Synonyms:cyclopent-3-ene-1,1-dicarboxylic acid;88326-51-6;3-cyclopentene-1,1-dicarboxylic acid;NSC120465;SCHEMBL2358074;DTXSID30298074;GSACUPQMFWTTOU-UHFFFAOYSA-N;MFCD20638529;cyclopent-3-ene-1,1-dicarboxylicacid;NSC-120465;AS-62511;S11594

Chemical Property of Cyclopent-3-ene-1,1-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 4.3E-07mmHg at 25°C
• Boiling Point: 387.8°Cat760mmHg
• Flash Point: 202.5°C
• PSA: 74.60000
• Density: 1.487g/cm³
• LogP: 0.49200
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 156.04225873
• Heavy Atom Count: 11
• Complexity: 205

Purity/Quality:

99% ^*data from raw suppliers

cyclopent-3-ene-1,1-dicarboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CCC1(C(=O)O)C(=O)O

Technology Process of Cyclopent-3-ene-1,1-dicarboxylic acid

There total 7 articles about Cyclopent-3-ene-1,1-dicarboxylic acid 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: 97.0%

Cyclopent-3-ene-1,1-dicarboxylic acid diethyl ester (21622-00-4) → Dimethyl 3-cyclopentene-1,1-dicarboxylate (88326-51-6)

Guidance literature:

With potassium hydroxide; In ethanol; at 70 ℃;

Reference yield: 67.0%

Dimethyl 3-cyclopentene-1,1-dicarboxylate (84646-68-4) → Dimethyl 3-cyclopentene-1,1-dicarboxylate (88326-51-6)

Guidance literature:

With water; potassium hydroxide; In ethanol; for 1h; Reflux;

DOI:10.1002/cmdc.201100248

Reference yield: 61.0%

2,2-diallylmalonic acid (4372-31-0) → Dimethyl 3-cyclopentene-1,1-dicarboxylate (88326-51-6)

Guidance literature:

With 2,2-Dimethyl-1-oxa-2-silacyclohexan; toluene-4-sulfonic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In methanol; water; at 75 ℃; for 27h;

DOI:10.1021/ja0642212

upstream raw materials:

Z-1,4-dichlorobutene

diethyl malonate

Cyclopent-3-ene-1,1-dicarboxylic acid diethyl ester

Dimethyl 3-cyclopentene-1,1-dicarboxylate

Downstream raw materials:

methyl cyclopent-3-ene-1-carboxylate

benzyl (2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-5,6-dihydro-4H-cyclopenta[d][1,3]thiazol-5-yl)carbamate

benzyl {2-[4-(3-chloropropoxy)phenyl]-5,6-dihydro-4H-cyclopenta[d][1,3]thiazol-5-yl}carbamate

trans-3,4-dibromocyclopentane-1-carboxylic acid

Refernces

• 1、 Kotha, Sambasivarao,Deb, Ashoke Chandra. "Design and synthesis of spiro-heterocycles by ring-closing metathesis". . p. 1120 - 1134. Retrieved 2008/12/23.
• 2、 Bashore, Crystal G.,Vetelino, Michael G.,Wirtz, Michael C.,Brooks, Paige R.,Frost, Heather N.,McDermott, Ruth E.,Whritenour, David C.,Ragan, John A.,Rutherford, Jennifer L.,Makowski, Teresa W.,Brenek, Steven J.,Coe, Jotham W.. "Enantioselective synthesis of nicotinic receptor probe 7,8-difluoro-1,2,3, 4,5,6-hexahydro-1,5-methano-3-benzazocine". . p. 5947 - 5950. Retrieved 2007/10/03.