72581-31-8

Basic information

• Product Name: Cyclopentanecarboxylic acid, 2-methylene-3-oxo-
• CAS NO: 72581-31-8
• Molecular Formula: C7H8O3
• Molecular Weight: 140.139
• Mol File: 72581-31-8.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: Cyclopentanecarboxylic acid, 2-methylene-3-oxo-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentanecarboxylic acid, 2-methylene-3-oxo-(72581-31-8)
• EPA Substance Registry System: Cyclopentanecarboxylic acid, 2-methylene-3-oxo-(72581-31-8)

Safety Data

• Hazardous Substances Data: 72581-31-8(Hazardous Substances Data)

Upstream product

• 5400-79-3 ethyl 3-oxocyclopentanecarboxylate 
• 50-00-0 formaldehyd 
• 189570-92-1 (+)-(2S,3S)-2-diethoxyphosphoryl-3-carboxycyclopentanone 
• 96258-20-7 3-<(phenylthio)dichloromethyl>-2-methylenecyclopentanone 
• 96258-21-8 sarkomycin phenyl thio ester 
• 82165-87-5 6-tetrahydropyranyloxymethyl-1,4-dioxaspiro<4.4>nonane-7-carboxylic acid 
• 72525-99-6 2-methylene 3-oxo methyl cyclopentane carboxylate 
• 82093-34-3 3a,5,6,6a-tetrahydro-3H-cyclopentafuran-1,4-dione 
• 75299-07-9 2-methylene-3-(cis-1-prop-1-enyl)cyclopentanone 
• 81310-07-8 6-Methoxymethyl-1,4-dioxa-spiro[4.4]nonane-7-carboxylic acid methyl ester 
• 123444-59-7 2-Diethoxyphosphoryl-3-carboxy-cyclopentanone 
• 930-30-3 cyclopent-2-enone 
• 1469357-21-8 (2R)-(tetrahydropyran-2-yloxymethyl)cyclopentanone-(3R)-carboxylic acid 
• 1469357-19-4 (3S)-(hex-1E-enyl)-(2R)-(tetrahydropyran-2-yloxymethyl)cyclopentanone 

Downstream Products

• 1909-79-1 2-methyl-2-cyclopenten-1-one-3-carboxylic acid 

Relevant articles and documents

Total synthesis of (R)-sarkomycin via asymmetric rhodium-catalyzed conjugate addition

(R)-Sarkomycin was prepared using a five-step total synthesis. Key steps in the enantioselective construction of the targeted scaffold were a rhodium-catalyzed asymmetric conjugate alkenyl addition with subsequent silyl trapping and a Mukaiyama aldol reaction with aqueous formaldehyde. Protection of the hydroxy group as a THP acetal and oxidative cleavage of the C,C-double bond provided a stable direct precursor to the natural product. The final liberation was carried out under slightly acidic conditions in a microwave-assisted reaction, resulting in a high yield of the deceptive sarkomycin. This represents the shortest enantioselective synthesis of this rather unstable compound to date and the first to employ asymmetric catalysis to introduce the stereogenic center.

Compound having effect of promoting neuron differentiation

A novel cystacycline derivative which has an excellent effect of promoting the differentiation of neurons and is useful as a remedy for central nervous system disorders, a remedy for peripheral nerve disorders, etc.

α-PHOSPHORYL CYCLOPENTANONES AS POSSIBLE INTERMEDIATES IN THE TOTAL SYNTHESIS OF SARKOMYCIN

In an effort to synthesize sarkomycin 1 trans-2-diphenylphosphinoyl-3-tris(methylthio)methyl-cyclopentanone 7 and trans-2-diphenylphosphinoyl-3-carbomethoxy-cyclopentanone 8 were prepared.The Horner-Wittig reaction of the latter with formaldehyde failed.