120419-97-8

Basic information

• Product Name: Silanamine, 1,1,1-trimethyl-N-(phenylmethylene)-, (E)-
• CAS NO: 120419-97-8
• Molecular Formula: C10H15NSi
• Molecular Weight: 177.321
• Mol File: 120419-97-8.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: Silanamine, 1,1,1-trimethyl-N-(phenylmethylene)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Silanamine, 1,1,1-trimethyl-N-(phenylmethylene)-, (E)-(120419-97-8)
• EPA Substance Registry System: Silanamine, 1,1,1-trimethyl-N-(phenylmethylene)-, (E)-(120419-97-8)

Safety Data

• Hazardous Substances Data: 120419-97-8(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 4039-32-1 lithium hexamethyldisilazane 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 15500-60-4 N,N-bis(trimethylsilyl)formamide 
• 591-51-5 phenyllithium 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 

Downstream Products

• 130697-55-1 (+)-(3S,4R)-3-Benzyloxy-4-phenylazetidin-2-one 
• 130632-19-8 (-)-(3R,4S)-3-Benzyloxy-4-phenylazetidin-2-one 
• 121910-45-0 C₁₇H₂₀N₂OSi 
• 141-05-9 Diethyl maleate 
• 121767-19-9 1-Phenyl-2-aza-3-trimethylsilyloxy-1,3-butadiene 
• 172095-47-5 (1E,3Z)-1,4-diphenyl-3-trimethylsilyloxy-2-aza-1,3-butadiene 
• 7486-93-3 3,3-dimethyl-4-phenylazetidin-2-one 
• 4383-23-7 (S)-1-phenylbut-3-en-1-amine 
• 115224-13-0 (R)-4-amino-4-phenyl-1-butene 
• 179743-16-9 (1Z,3E)-1-phthalimido-2-(trimethylsilyl)oxy-3-aza-4-phenyl-1,3-butadiene 
• 517920-41-1 (S)-4-Isopropyl-3-((3R,4S)-3-methyl-4-phenyl-3,4-dihydro-azet-2-yl)-thiazolidine-2-thione 
• 341979-61-1 3-methoxy-2-phenyl-2,5-dihydropyrrole 

Relevant articles and documents

Lewis acid-catalyzed electrocyclization of 2-aza-1,3-butadienes to NH-β-lactams

Lewis acid-catalyzed cyclization of 2-aza-3-trimethylsilyloxy-buta-1,3-diene is reported. Stereochemical differences with the uncatalyzed cyclization are discussed.

Catalytic enantioselective one-pot aminoborylation of aldehydes: A strategy for construction of nonracemic α-amino boronates

We report a strategy for the conversion of aldehydes to enantiomerically enriched α-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B2(pin)s

Enantioselective addition of β-functionalized allylboronates to aldehydes and aldimines. Stereocontrolled synthesis of α-methylene-γ-lactones and lactams

We report results regarding the development of condensations of chiral β-alkoxycarbonylallylboronates on aldehydes and imines. These allylboronates add in a highly enantioselective and diastereospecific manner to afford biologically and synthetically useful chiral α-methylene-γ-butyrolactones and lactams. The nature of the electrophile (aldehyde vs imine) is shown to have a dramatic influence on the mechanism of the reaction, probably directing the stereoselectivity of the process through different transition states.

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.