59498-98-5

Basic information

• Product Name: 1-Methyl-2-oxabicyclo[2.2.2]octan-3-one
• Synonyms: 1-Methyl-2-oxabicyclo[2.2.2]octan-3-one
• CAS NO: 59498-98-5
• Molecular Weight: 140.182
• Mol File: 59498-98-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-Methyl-2-oxabicyclo[2.2.2]octan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-2-oxabicyclo[2.2.2]octan-3-one(59498-98-5)
• EPA Substance Registry System: 1-Methyl-2-oxabicyclo[2.2.2]octan-3-one(59498-98-5)

Safety Data

• Hazardous Substances Data: 59498-98-5(Hazardous Substances Data)

Upstream product

• 6297-22-9 4-carbomethoxycyclohexanone 
• 676-58-4 methylmagnesium chloride 
• 917-64-6 methyl magnesium iodide 
• 79-10-7 acrylic acid 
• 78-79-5 isoprene 

Downstream Products

• 85977-96-4 4c-hydroxy-4t-methyl-cyclohexane-r-carboxylic acid methyl ester 
• 58336-10-0 cis-4-(hydroxymethyl)-1-methylcyclohexan-1-ol 

Relevant articles and documents

ALKYLATION OF δ-KETOESTERS : A MECHANISM CHANGE DEPENDING ON CONFORMATIONAL MOBILITY AND SUBSTITUENT EFFECTS ON STEREOSELECTION.

Kinetic evidence shows that the two groups of a δ-ketoester can interact in the transition state of a Grignard reaction.This promotes high stereoselectivity by chiral center far from the ketonic group and produces good correlations between stereoselection and electronic effects of substituents.

A CASE OF STEREOSELECTIVITY CHANGE IN GRIGNARD REACTION COMPETITION EXPERIMENTS

The stereochemical product ratio 2/3 of cis- and trans-1-methyl-2-oxabicyclo-decan-3-ones derived from methyl 3-(2-oxocyclohexyl)propanoate, 1, with MeMgI in C6H6 regularly increase in competition reactions with 4-oxocyclohexanecarboxylic acid methyl ester, 4, as the amount of the last-mentioned compound increases.This effect is related to the total concentration of keto esters in the reaction mixture.Competition experiments were also performed in THF with MeMgCl: no drift in 2/3 ratio was observed.