23457-03-6

Basic information

• Product Name: Ethanone, 1-(2-methyl-3,3-diphenyloxiranyl)-
• Synonyms: 2-acetyl-1,2-epoxy-1,1-diphenylpropane;3,4-epoxy-3-methyl-4,4-diphenylbutan-2-one
• CAS NO: 23457-03-6
• Molecular Formula: C17H16O2
• Molecular Weight: 252.30800
• Mol File: 23457-03-6.mol

Chemical Properties

• CAS DataBase Reference: Ethanone, 1-(2-methyl-3,3-diphenyloxiranyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(2-methyl-3,3-diphenyloxiranyl)-(23457-03-6)
• EPA Substance Registry System: Ethanone, 1-(2-methyl-3,3-diphenyloxiranyl)-(23457-03-6)

Safety Data

• Hazardous Substances Data: 23457-03-6(Hazardous Substances Data)

Upstream product

• 181038-11-9 1-(4,4-dimethyl-2-oxazolin-2-yl)-1,2-epoxy-2,2-diphenylethane 
• 212071-84-6 2-(4,4-dimethyl-2-oxazolin-2-yl)-1,2-epoxy-1,1-diphenylpropane 
• 212072-14-5 2,3,4,4-Tetramethyl-2-(2-methyl-3,3-diphenyl-oxiranyl)-oxazolidine 
• 2466-76-4 N-Acetylimidazole 

Relevant articles and documents

Generation of oxiranyllithiums and oxiranyl Grignard reagents having a carbanion-destabilizing group from sulfinyloxiranes: Their property and an application to asymmetric synthesis of epoxides and alcohols

The first generation of oxiranyllithiums and oxiranyl Grignard reagents having a carbanion-destabilizing group (alkyl group) was realized from sulfinyloxiranes via the ligand exchange reaction of sulfoxides with tert- butyllithium or ethylmagnesium chlori

Deprotonation of oxazolinyloxiranes: Formation of substituted acyloxiranes

Deprotonation of oxazolinyloxiranes 1a, 1h, and 1k with sBuLi/TMEDA at - 100 °C in Et2O furnishes oxazolinyloxiranyllithium compounds 1b, 1i, and 1I which are stable at low temperature and can be trapped with electrophiles to give substituted oxiranes 1c-1g and 1j. The reaction of 1b with aldehydes produced diastereomers syn (2a-d) and anti (3a-d). Oxiranyllithium 1i from trans-1-(4,4-dimethyl-2-oxazolinyl)-2-p-tolylepoxy-ethane (1h) was found to be configurationally stable while oxiranyllithium 1l, generated from the cis isomer 1k, was not. Oxazolinylepoxides 1d, 1j, and 1m could be deblocked to acyloxiranes 5a-e through oxazolidines 4a-e.

An efficient synthesis of oxiranyl oxazolines and elaboration to acyl oxiranes

Deprotonation of oxazolinyl oxirane 1a with sec-BuLi/TMEDA at -100 °C in Et20 furnished oxazolinyl oxiranyllithium 1b, which could be trapped with electrophiles to give oxiranes 1c-g. The reaction of 1b with aldehydes produced diastereomers syn (2a-d) and anti (3a-d). Oxiranyllithium 1i from trans-1-oxazolinyl-2-p-tolyl epoxy ethane 1h was found to be configurationally stable while oxiranyllithium 1I, generated from the cis isomer 1k, was not. Oxazolinyl epoxides 1d, 1j and 1m could be deblocked to acyl oxiranes 5a-e through oxazolidines 4a-e.

The First Example of Oxiranyllithium and Oxiranyl Grignard Reagent Having a Carbanion Destabilizing Group: Generation, Property, and Some Synthetic Uses

The first generation of destablized oxiranyllithium and oxiranyl Grignard reagent from sulfinyloxiranes with t-BuLi or EtMgCl is described.Treatment of α-methyl α,β-epoxy sulfoxide (sulfinyloxirane) with t-BuLi in THF at -100 deg C gave oxiranyllithium ha