92015-67-3

Basic information

• Product Name: [(S)-2-Methyl-cyclohex-(E)-ylidene]-acetic acid methyl ester
• CAS NO: 92015-67-3
• Molecular Weight: 168.236
• Mol File: 92015-67-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [(S)-2-Methyl-cyclohex-(E)-ylidene]-acetic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [(S)-2-Methyl-cyclohex-(E)-ylidene]-acetic acid methyl ester(92015-67-3)
• EPA Substance Registry System: [(S)-2-Methyl-cyclohex-(E)-ylidene]-acetic acid methyl ester(92015-67-3)

Safety Data

• Hazardous Substances Data: 92015-67-3(Hazardous Substances Data)

Upstream product

• 74-88-4 methyl iodide 
• 2916-76-9 methyl (trimethylsilyl)acetate 
• 583-60-8 2-Methylcyclohexanone 
• 85114-28-9 (E,2S)-(-)-(2-methylcyclohexylidene)acetic acid 
• 85114-27-8 (E,2S)-(-)-(2-methylcyclohexylidene)bromomethane 
• 85114-25-6 (Z,2S)-(+)-(2-methylcyclohexylidene)acetic acid 

Downstream Products

• 85048-41-5 (E,2S)-(+)-(2-methylcyclohexylidene)ethanol 
• 85048-43-7 (E,2S)-(+)-(2-methylcyclohexylidene)propene 
• 85048-42-6 (E,2S)-(-)-(2-methylcyclohexylidene)acetaldehyde 

Relevant articles and documents

Quantum chemical calculations on the Peterson olefination with α-silyl ester enolates

The reaction of stabilized Peterson reagents (α-silyl ester enolates) with ketones has been studied theoretically and experimentally. Enolate geometry was studied by trapping experiments and NMR spectroscopy and was found to differ markedly with the nature of the base (LiHMDS vs LDA vs KHMDS). The chelating effect of the lithium counterion was found to be critical for the reaction. For the two ketones studied, the combined weight of experimental and computational data assigns geometrical selectivity to the initial addition transition state, though in general there appears to be a fine balance between three possible choices for the rate-determining step.