24863-70-5

Basic information

• Product Name: methyl 2-(3-oxo-2-pentyl-1-cyclopentenyl)acetate
• Synonyms: methyl 2-(3-oxo-2-pentyl-1-cyclopentenyl)acetate;2-Pentyl-3-oxo-1-cyclopentene-1-acetic acid methyl ester;3-Oxo-2-pentyl-1-cyclopentene-1-acetic acid methyl ester;1-Cyclopentene-1-acetic acid, 3-oxo-2-pentyl-, methyl ester
• CAS NO: 24863-70-5
• Molecular Formula: C₁₃H₂₀O₃
• Molecular Weight: 224.2961
• Mol File: 24863-70-5.mol

Chemical Properties

• Boiling Point: 327.5 °C at 760 mmHg
• Flash Point: 141.6 °C
• Appearance: /
• Density: 1.023 g/cm³
• Vapor Pressure: 0.000202mmHg at 25°C
• Refractive Index: 1.475
• CAS DataBase Reference: methyl 2-(3-oxo-2-pentyl-1-cyclopentenyl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-(3-oxo-2-pentyl-1-cyclopentenyl)acetate(24863-70-5)
• EPA Substance Registry System: methyl 2-(3-oxo-2-pentyl-1-cyclopentenyl)acetate(24863-70-5)

Safety Data

• Hazardous Substances Data: 24863-70-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h3-9H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 128893-61-8 3-(2-Cyano-ethyl)-4-oxo-nonanoic acid methyl ester 

Downstream Products

• 1128-08-1 dihydro-cis-jasmone 
• 128087-96-7 cis methyl dehydrojasmonate 
• 128087-96-7 methyl dihydrojasmonate(trans) 
• 151716-36-8 trans-methyl ((1S,2S)-2-pentyl-3-oxocyclopentyl)acetate 
• 128087-96-7 (-)-cis-Methyl dihydrojasmonate 
• 2630-39-9 methyl dihydro jasmonate 
• 39647-11-5 <2S*,3R*>-3-methoxycarbonylmethyl-2-pentylcyclopentanone(methyl dihydroepijasmonate) 
• 24851-98-7 methyl 3-oxo-2-pentylcyclopentaneacetate 
• 2570-03-8 (+/-)-methyl trans-dihydrojasmonate 
• 2570-03-8 (+/-)-methyl dihydroepijasmonate 

Relevant articles and documents

A new synthesis of methyl 3-oxo-2-pentyl-1-cyclopentene-1-acetate

The 92:8 equilibrium mixture of (±)-trans-methyl dihydrojasmonate (1) and its cis-isomer is transformed in 63% overall yield into the title compound 4 by epoxidation of the derived enol acetate 2 with peracetic acid/Na2CO3 in toluene and heating the resulting α-acetoxy epoxide 3 in MeOH in the presence of catalytic amounts of methanesulfonic acid.

Electroorganic Chemistry. 140. Electroreductively Intra- and Intermolecular Couplings of Ketones with Nitriles

Electroreduction of γ- and δ-cyano ketones in i-PrOH with Sn cathode gave α-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products.Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of γ- and δ-cyano ketones in one of the key steps.Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product.The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.

ELECTROREDUCTIVE INTRAMOLECULAR COUPLING OF γ- AND δ-CYANOKETONES

Electroreduction of γ- and δ-cyanoketones in i-PrOH gave cyclized products α-hydroxyketones and their dehydroxylated ketones, and this reaction was applied to the synthesis of dihydrojasmone, methyl dihydrojasmonate, and Rosaprostol.