331258-76-5

Basic information

• Product Name: (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone
• Synonyms: (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone
• CAS NO: 331258-76-5
• Molecular Weight: 329.396
• Mol File: 331258-76-5.mol

Chemical Properties

• CAS DataBase Reference: (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone(331258-76-5)
• EPA Substance Registry System: (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone(331258-76-5)

Safety Data

• Hazardous Substances Data: 331258-76-5(Hazardous Substances Data)

Upstream product

• 701-99-5 Phenoxyacetyl chloride 

Downstream Products

• 265650-98-4 C₁₆H₁₈N₂O₃ 
• 251480-07-6 (3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone 
• 251480-04-3 (+)-(2R,3R)-1-(4-pentynyl)-3-phenoxy-4-oxoazetidine-2-carbaldehyde 

Relevant articles and documents

Straightforward asymmetric entry to highly functionalized medium-sized rings fused to β-lactams via chemo- and stereocontrolled divergent radical cyclization of Baylis-Hillman adducts derived from 4-oxoazetidine-2-carbaldehydes

DABCO promoted reactions of various activated vinyl systems with optically pure 4-oxoazetidine-2-carbaldehydes 1 gave rise to Baylis - Hillman adducts 3 with excellent syn stereoselectivities, without detectable racemization. Products 3 are used for the asymmetric preparation of unusual 2-azetidinones fused to medium-sized rings via chemo- and stereocontrolled divergent radical cyclization. The formation of bicyclic β-lactams 4 - 6 could be rationalized through a tandem radical Michael addition/endo cyclization or a tandem radical addition/Michael addition, depending on the electronic nature of the radical promoter.

Reverse-Cope elimination versus 1,3-dipolar cycloaddition in the reaction of enantiopure 2-azetidinone-tethered alkynylaldehydes with N- methylhydroxylamine

Enantiopure 2-azetidinone-tethered alkynylaldehydes 1 react stereoselectively under mild conditions with N-methylhydroxylamine to yield products derived from either intramolecular reverse-Cope elimination or 1,3- dipolar cycloaddition, depending on both t