Cyclopentanecarboxylic acid, 2-methylene-3-oxo-

Base Information

• Chemical Name: Cyclopentanecarboxylic acid, 2-methylene-3-oxo-
• CAS No.: 72581-31-8
• Molecular Formula: C7H8O3
• Molecular Weight: 140.139
• DSSTox Substance ID: DTXSID90871685
• Nikkaji Number: J175.453J
• Wikidata: Q105115168
• ChEMBL ID: CHEMBL2008585
• Mol file: 72581-31-8.mol

Synonyms:Sarkomycin;2-methylidene-3-oxocyclopentane-1-carboxylic acid;874-21-5;C7H7O3.Na;C7-H7-O3.Na;NSC14347;Cyclopentanecarboxylic acid, 2-methylene-3-oxo-;SCHEMBL596950;CHEMBL2008585;DTXSID90871685;AKOS006377430;69274-56-2;NCI60_000955;2-methylene-3-oxocyclopentanecarboxylic acid;2-methylene-3-oxo-cyclopentanecarboxylic acid

Chemical Property of Cyclopentanecarboxylic acid, 2-methylene-3-oxo-

Chemical Property:

• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 140.047344113
• Heavy Atom Count: 10
• Complexity: 205

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Cyclopentanecarboxylic acid, 2-methylene-3-oxo-

There total 72 articles about Cyclopentanecarboxylic acid, 2-methylene-3-oxo- 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: 86.0%

(2R)-(tetrahydropyran-2-yloxymethyl)cyclopentanone-(3R)-carboxylic acid (1469357-21-8) → sarkomycin (69274-56-2,72581-31-8,143954-86-3,489-21-4,11031-48-4)

Guidance literature:

With ion-exchange resin Lewatit K₂₆₁₁; In acetone; at 60 ℃; for 1h; Solvent; Reagent/catalyst; Temperature; Time; Microwave irradiation; Inert atmosphere;

DOI:10.1021/jo4016979

Reference yield: 80.0%

3-<(phenylthio)dichloromethyl>-2-methylenecyclopentanone (96258-20-7) → sarkomycin (72581-31-8,11031-48-4) + sarkomycin phenyl thio ester (96258-21-8)

Guidance literature:

With 3-methyl-4-hydroxy-5-tert-butylbenzenethiol; silver trifluoroacetate; In tetrahydrofuran; water; at 25 ℃; for 2h;

DOI:10.1021/jo00216a031

Reference yield: 45.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-Diethoxyphosphoryl-3-carboxy-cyclopentanone (123444-59-7) → sarkomycin (72581-31-8,11031-48-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 2h; Heating;

DOI:10.1016/S0040-4039(01)80382-8

upstream raw materials:

ethyl 3-oxocyclopentanecarboxylate

formaldehyd

2-Diethoxyphosphoryl-3-carboxy-cyclopentanone

6-Methoxymethyl-1,4-dioxa-spiro[4.4]nonane-7-carboxylic acid methyl ester

Downstream raw materials:

2-methyl-2-cyclopenten-1-one-3-carboxylic acid

Refernces

• 1、 Kar, Anirban,Argade, Narshinha P.. "A simple synthesis of (±)-sarkomycin". . p. 1234 - 1236. Retrieved 2007/10/03.
• 2、 Miko?ajczyk, Marian,Zurawiński, Remigiusz,Kie?basin?ski, Piotr,Wieczorek, Micha? W.,B?aszczyk, Jaros?aw,Majzner, Wies?aw R.. "Total synthesis of racemic and optically active sarkomycin". . p. 356 - 365. Retrieved 2007/10/03.