120419-99-0

Basic information

• Product Name: 4-phenyl-1-trimethylsilyl-1-azabuta-1,3-diene
• Synonyms: 4-phenyl-1-trimethylsilyl-1-azabuta-1,3-diene
• CAS NO: 120419-99-0
• Molecular Weight: 203.359
• Mol File: 120419-99-0.mol

Chemical Properties

• CAS DataBase Reference: 4-phenyl-1-trimethylsilyl-1-azabuta-1,3-diene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-phenyl-1-trimethylsilyl-1-azabuta-1,3-diene(120419-99-0)
• EPA Substance Registry System: 4-phenyl-1-trimethylsilyl-1-azabuta-1,3-diene(120419-99-0)

Safety Data

• Hazardous Substances Data: 120419-99-0(Hazardous Substances Data)

Upstream product

• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 

Downstream Products

• 179743-17-0 C₂₂H₂₂N₂O₃Si 
• 135299-43-3 5-chloro-8-chloromethyl-3,3-dimethyl-6-phenyl-7-thianonanam 
• 135299-42-2 8-chloro-3,3-dimethyl-5-(α-chlorobenzyl)-6-thianonanam 
• 137845-37-5 4-methyl-N-((1E,2E)-3-phenylallylidene)benzenesulfonamide 
• 135299-41-1 1-Allyl-3,3-dimethyl-4-((E)-styryl)-azetidin-2-one 

Relevant articles and documents

Asymmetric allylboration of acyl imines catalyzed by chiral diols

Chiral BINOL-derived diols catalyze the enantioselective asymmetric allylboration of acyl imines. The reaction requires 15 mol % (S)-3,3′-Ph2-BINOL as the catalyst and allyldiisopropoxyborane as the nucleophile. The reaction products are obtained in good yields (75-94%) and high enantiomeric ratios (95:5-99.5:0.5) for aromatic and aliphatic imines. High diastereoselectivities (diastereomeric ratio > 98:2) and enantioselectivities (enantiomeric ratio > 98:2) are obtained in the reactions of acyl imines with crotyldiisopropoxyboranes. This asymmetric transformation is directly applied to the synthesis of Maraviroc, the selective CCR5 antagonist with potent activity against HIV-1 infection. Mechanistic investigations of the allylboration reaction including IR, NMR, and mass spectrometry studies indicate that acyclic boronates are activated by chiral diols via exchange of one of the boronate alkoxy groups with activation of the acyl imine via hydrogen bonding.

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.