179743-16-9

Basic information

• Product Name: (1Z,3E)-1-phthalimido-2-(trimethylsilyl)oxy-3-aza-4-phenyl-1,3-butadiene
• CAS NO: 179743-16-9
• Molecular Weight: 364.476
• Mol File: 179743-16-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1Z,3E)-1-phthalimido-2-(trimethylsilyl)oxy-3-aza-4-phenyl-1,3-butadiene(CAS DataBase Reference)
• NIST Chemistry Reference: (1Z,3E)-1-phthalimido-2-(trimethylsilyl)oxy-3-aza-4-phenyl-1,3-butadiene(179743-16-9)
• EPA Substance Registry System: (1Z,3E)-1-phthalimido-2-(trimethylsilyl)oxy-3-aza-4-phenyl-1,3-butadiene(179743-16-9)

Safety Data

• Hazardous Substances Data: 179743-16-9(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 16118-22-2 benzylidenamine 
• 6780-38-7 N-phthaloylglycine chloride 
• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 120419-97-8 (E)-N-benzylidene-1,1,1-trimethylsilanamine 

Downstream Products

• 213335-87-6 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-butyramide 

Relevant articles and documents

Synthesis of perhydroxazin-4-ones. Competitive Mukaiyama versus hetero Diels-Alder reaction in the cycloaddition of 2-aza-3-trimethylsilyloxy-1,3-butadiene and aldehydes

The reactions of 2-aza-3-trimethylsilyloxy-1,3-butadiene with carbonyl dienophiles are described. 2-Aza-1,3-butadienes participate as dienes in the [4+2] cycloaddition with aldehydes to afford perhydroxazin-4-ones in good yields. Experimental results, however, show that a Mukaiyama type two-step reaction must be taken into account. The cycloadducts obtained have proved to be useful intermediates in the synthesis of α-amino-β-hydroxy acids.

Trans -diastereoselective synthesis of 3-phthalimido β-lactams via a two step-Staudinger reaction

New conditions for the Staudinger reaction provide N-unsubstituted-3- phthalimido-β-lactams in satisfactory yields with complete trans- selectivity.