101067-57-6

Basic information

• Product Name: 2-Azetidinone, 3-phenoxy-4-phenyl-
• CAS NO: 101067-57-6
• Molecular Formula: C15H13NO2
• Molecular Weight: 239.274
• Mol File: 101067-57-6.mol

Chemical Properties

• CAS DataBase Reference: 2-Azetidinone, 3-phenoxy-4-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone, 3-phenoxy-4-phenyl-(101067-57-6)
• EPA Substance Registry System: 2-Azetidinone, 3-phenoxy-4-phenyl-(101067-57-6)

Safety Data

• Hazardous Substances Data: 101067-57-6(Hazardous Substances Data)

Upstream product

• 701-99-5 Phenoxyacetyl chloride 
• 100-52-7 benzaldehyde 
• 54150-57-1 2-benzoyloxyacetyl chloride 
• 128989-66-2 cis-3-Phenoxy-4-phenyl-1-(1'-hydroxyethyl)-2-azetidinone 
• 122-59-8 2-phenoxyacetic acid 
• 101067-62-3 2-phenyl-N-benzylidenethanolamine 
• 111761-81-0 1-benzoylmethyl-3-phenoxy-4-phenylazetidin-2-one 
• 111821-16-0 1-(hydroxypropyl)-3-phenoxy-4-phenylazetidin-2-one 
• 111761-82-1 1-acetonyl-3-phenoxy-4-phenylazetidin-2-one 
• 97934-56-0 1-(2-Hydroxy-2-phenyl-ethyl)-3-phenoxy-4-phenyl-azetidin-2-one 
• 101067-56-5 3-Phenoxy-4-phenyl-1-((E)-styryl)-azetidin-2-one 
• 111867-59-5 N-(p-dimethyl-t-butylsiloxybenzylidene)-p-methoxyaniline. 
• 3230-39-5 4-{[1-(4-Methoxy-phenyl)-meth-(Z)-ylidene]-amino}-phenol 
• 123-11-5 4-methoxy-benzaldehyde 

Relevant articles and documents

A new entry to N-unsubstituted β-lactams through a solid-phase approach

A remarkable new entry to N-unsubstituted β-lactams using rink resin as the solid-support has been developed.

Soluble-polymer-supported synthesis of β-lactams on a modified poly(ethylene glycol)

A modified poly(ethylene glycol) (PEG) has been developed for the soluble-polymer-supported synthesis of β-lactams. The monomethylether of PEG (MeOPEG) with an average Mw of 5000 was used as the support, a 4-(3-propyl)phenyl residue as the spacer, and a 4-oxyphenylamino group as the moiety with the reactive functionality. From this modified PEG representative aromatic, heteroaromatic, unsaturated, and aliphatic imines were obtained in high yields by different procedures. The polymer-supported imines were then employed to prepare several β-lactams by enolate/imine condensation and ketene/ imine cycloaddition. Examples of the control of the absolute stereochemistry during the azetidinone ring formation are also reported. The reactions carried out on the polymer-bound imines showed a remarkable similarity to those performed on nonimmobilized imines, both in terms of yields and stereoselectivities. Removal of the β-lactams from the polymer has also been accomplished to directly deliver the N-unsubstituted azetidinones.

Synthesis of N1-unsubstituted β-lactams via a facile deprotection of N1-[(α-thiophenyl)benzyl] group

A diastereoselective synthesis of (±) c/s-β-1actams (5 and 6) via cycloaddition reactions of N1-(α-thiophenyl)benzyl imines (3) with acid chlorides (4) in the presence of triethylamine is described. The deprotection of N1-(α-thiophenyl)benzyl group has been achieved by oxidation using potassium persulfate to give N-unsubstituted β-lactams (7) in good yields.

Synthesis of N1-unsubstituted (β-lactams : Introducing n1-(1'-thiophenyl)benzyl as an N-protecting group

A diastereoselective synthesis of (±) cis-β-lactams (5 and 6) via cycloaddition reaction of N1-(α-thiophenyl)benzyl imines (3) with acid chlorides (4) in the presence of triethyl amine is described. Deprotection of N1-(α-thiophenyl)benzyl group was achieved in good yields by oxidation using potassium persulfate.

Stereocontrolled Synthesis of N-Vinyl-, N-(1'-Propenyl)-, and N-Unsubstituted-β-lactams from 2-Aza-1,3-butadienes via the Staudinger Reaction

2-Aza-1,3-butadienes 2 and 5 were synthesized in good yields and on a large scale.Reaction of 2 and 5 with acid chlorides in the presence of triethylamine (Staudinger reaction) resulted in the high-yielding formation of N-vinyl- and N-(1'-propenyl)-β-lact

N-vinyl and N-unsubstituted β-lactams from 1-substituted 2-aza-1,3-butadienes

The reaction of acid chlorides and N-vinyl imines results in the stereoselective formation of cis N-vinyl β-lactams. The N-vinyl protecting group can be removed either oxidatively or hydrolytically to yield N-substituted β-lactams.

2-AZA-1,3-DIENES AS NOVEL PRECURSORS FOR THE SYNTHESIS OF N-UNSUBSTITUTED β-LACTAMS. A THREE STEP SYNTHESIS OF 4-ACETOXY-3-PHENOXY-2-AZETIDINONE

2-Aza-1,3-dienes, prepared in excellent yields from aldehydes and readily available allylamine, were utilized to synthesize N-(1-propenyl)-β-lactams.Oxidative cleavage of the N-protecting group produced N-unsubstituted β-lactams. 4-Acetoxy-3-phenoxy-2-aze

Reagents and Synthetic Methods. Part 58. Synthesis of β-Lactams from Acetic Acids and Imines promoted by Vilsmeier Type Reagents

The development of a practical method for the stereospecific preparation of several 3-substituted β-lactams from acetic acids and imines is described.The key step of the method is the activation of the carboxy component by means of Vilsmeier type reagents.The preparation of some N-(2'-hydroxyethyl)-β-lactams and N-(p-dimethyl-t-butylsiloxyphenyl)-β-lactams as intermediates for N-H azetidinones is also reported.For the last compounds the steric bulk of the N-substituent is the key feature for a high cis-β-lactam formation.

A NOVEL SYNTHETIC APPROACH TO N-UNSUBSTITUTED β-LACTAMS

A convenient simple route to N-unsubstituted β-lactams is described.Formation of unusual N-styryl-β-lactams is the key of the method.