5453-05-4

Basic information

• Product Name: methyl 2-methyl-3-oxo-cyclopentene-1-carboxylate
• Synonyms: methyl 2-methyl-3-oxo-cyclopentene-1-carboxylate
• CAS NO: 5453-05-4
• Molecular Formula: C₈H₁₀O₃
• Molecular Weight: 0
• Mol File: 5453-05-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 226.1°C at 760 mmHg
• Flash Point: 92.5°C
• Appearance: /
• Density: 1.167g/cm³
• Vapor Pressure: 0.0836mmHg at 25°C
• Refractive Index: 1.493
• CAS DataBase Reference: methyl 2-methyl-3-oxo-cyclopentene-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-methyl-3-oxo-cyclopentene-1-carboxylate(5453-05-4)
• EPA Substance Registry System: methyl 2-methyl-3-oxo-cyclopentene-1-carboxylate(5453-05-4)

Safety Data

• Hazardous Substances Data: 5453-05-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H10O3/c1-5-6(8(10)11-2)3-4-7(5)9/h3-4H2,1-2H3

Upstream product

• 785809-11-2 5-hydroxy-2-methyl-3-oxo-cyclopent-1-enecarboxylic acid 
• 146860-08-4 (+/-)-methyl 3-hydroxy-2-methylcyclopent-1-enecarboxylate 
• 765-69-5 2-Methylcyclopentane-1,3-dione 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 56671-87-5 3-Bromo-2-methylcyclopent-2-en-1-one 
• 5870-63-3 3-hydroxy-2-methyl-2-cyclopenten-1-one 
• 56778-49-5 3-iodo-2-methyl-2-cyclopentenone 

Downstream Products

• 7509-75-3 3-hydrazono-2-methyl-cyclopent-1-enecarboxylic acid hydrazide 
• 100885-40-3 3-(2,4-dinitro-phenylhydrazono)-2-methyl-cyclopent-1-enecarboxylic acid methyl ester 
• 459174-10-8 (S)-(-)-methyl 3-hydroxy-2-methylcyclopent-1-enecarboxylate 
• 459174-16-4 (2S,3S)-3-Hydroxy-2-methyl-cyclopentanecarboxylic acid methyl ester 

Relevant articles and documents

Photoredox-Catalyzed Isomerization of Highly Substituted Allylic Alcohols by C?H Bond Activation

Photoredox-catalyzed isomerization of γ-carbonyl-substituted allylic alcohols to their corresponding carbonyl compounds was achieved for the first time by C?H bond activation. This catalytic redox-neutral process resulted in the synthesis of 1,4-dicarbonyl compounds. Notably, allylic alcohols bearing tetrasubstituted olefins can also be transformed into their corresponding carbonyl compounds. Density functional theory calculations show that the carbonyl group at the γ-position of allylic alcohols are beneficial to the formation of their corresponding allylic alcohol radicals with high vertical electron affinity, which contributes to the completion of the photoredox catalytic cycle.

The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: Reaction development, scope, and applications

The first palladium-catalyzed enantioselective oxidation of secondary alcohols has been developed, utilizing the readily available diamine (-)-sparteine as a chiral ligand and molecular oxygen as the stoichiometric oxidant. Mechanistic insights regarding the role of the base and hydrogen-bond donors have resulted in several improvements to the original system. Namely, addition of cesium carbonate and tert-butyl alcohol greatly enhances reaction rates, promoting rapid resolutions. The use of chloroform as solvent allows the use of ambient air as the terminal oxidant at 23°C, resulting in enhanced catalyst selectivity. These improved reaction conditions have permitted the successful kinetic resolution of benzylic, allylic, and cyclopropyl secondary alcohols to high enantiomeric excess with good-toexcellent selectivity factors. This catalyst system has also been applied to the desymmetrization of meso-diols, providing high yields of enantioenriched hydroxyketones.