17197-57-8

Basic information

• Product Name: 3-Phenylazetidin-2-one
• Synonyms: 3-Phenylazetidin-2-one;L-1759
• CAS NO: 17197-57-8
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• Mol File: 17197-57-8.mol

Chemical Properties

• Boiling Point: 353.8°C at 760 mmHg
• Flash Point: 205.5°C
• Appearance: /
• Density: 1.152g/cm³
• Vapor Pressure: 3.5E-05mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: 3-Phenylazetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Phenylazetidin-2-one(17197-57-8)
• EPA Substance Registry System: 3-Phenylazetidin-2-one(17197-57-8)

Safety Data

• Hazardous Substances Data: 17197-57-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H9NO/c11-9-8(6-10-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,10,11)

Upstream product

• 135959-07-8 α-(aminomethyl)benzeneacetic acid,ethyl ester 
• 184423-97-0 N-(4-methoxyphenyl)-3-phenylazetidin-2-one 
• 133505-02-9 cis-1-(p-methoxyphenyl)-4-formyl-3-phenyl-2-azetidinone 
• 184423-91-4 3-hydroxy-N-(4-methoxyphenyl)-2-phenylpropanamide 

Relevant articles and documents

Stereoselective synthesis of 3-substituted 4-(formyloxy)-2-azetidinones by the unusual Baeyer-Villiger reaction of β-lactam aldehydes. Scope and synthetic applications

The Baeyer-Villiger oxidation of 4-formyl-β-lactams 1 with m-CPBA gave 4-(formyloxy) β-lactams 2 in a simple, efficient, and totally stereoselective process. This reaction is one of the scarce examples of the preferred migration of a carbon moiety in an aliphatic aldehyde. The influence of the substituents at N1 and C3 of the four-membered ring in the Baeyer-Villiger rearrangement has been studied. Thus, alkyl, alkenyl, aryl, and alkyloxy 3-substituted-1-(p-anisyl)-2-azetidinones 1 form exclusively 4-(formyloxy) β-lactams 2. Amide or acetoxy substituents at C3 of the four membered ring produce mixtures of 4-(formyloxy) β-lactams 2 and 4-carboxy β-lactams 5. The exclusive formation of carboxy derivatives is observed sometimes for 1-alkyl-substituted-2-azetidinones 1. 4-(Formyloxy) β-lactams 2 are suitable starting materials to prepare different 4-unsubstituted β-lactams 9 using β-hydroxy amides 8 as isolable intermediates. The overall transformation 4-formyl-2-azetidinone to 4-unsubstituted β-lactam is an easy and convenient stereoselective route to these interesting types of compounds.

The unusual Baeyer-Villiger rearrangement of β-lactam aldehdyes: Totally stereoselective entry to cis-3-substituted 4-formyloxy-2-azetidinones

Baeyer-Villiger oxidation of 4-formyl-β-lactams 1 with m-chloroperbenzoic acid in dichloromethane at room temperature is shown to be a convenient method for the preparation of 4-formyloxy-β-lactams 2. Some reactions of novel compounds 2 are also described