90606-10-3

Basic information

• Product Name: Methanamine, N-(phenylmethylene)-1-(trimethylsilyl)-, (E)-
• CAS NO: 90606-10-3
• Molecular Formula: C11H17NSi
• Molecular Weight: 191.348
• Mol File: 90606-10-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Methanamine, N-(phenylmethylene)-1-(trimethylsilyl)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanamine, N-(phenylmethylene)-1-(trimethylsilyl)-, (E)-(90606-10-3)
• EPA Substance Registry System: Methanamine, N-(phenylmethylene)-1-(trimethylsilyl)-, (E)-(90606-10-3)

Safety Data

• Hazardous Substances Data: 90606-10-3(Hazardous Substances Data)

Upstream product

• 18166-02-4 N-trimethylsilylmethylamine 
• 100-52-7 benzaldehyde 
• 90606-07-8 <<(trimethylsilyl)methyl>imino>triphenylphosphorane 
• 883627-50-7 N-trimethylsilylmethyl P-trimethyl-λ⁵-phosphazene 
• 75-77-4 chloro-trimethyl-silane 
• 622-29-7 N-Benzylidenemethylamine 
• 87576-94-1 trimethylsilylmethyl azide 

Downstream Products

• 105435-23-2 dimethyl 1-methoxycarbonyl-2-phenyl-3-pyrroline-3,4-dicarboxylate 
• 104156-73-2 Trifluoro-methanesulfonatemethyl-[1-phenyl-meth-(Z)-ylidene]-trimethylsilanylmethyl-ammonium; 
• 104156-40-3 1-methyl-2-phenyl-3,4-bis(hydroxymethyl)-3-pyrroline 
• 104156-41-4 1-methyl-2-phenyl-3,4-bis<<(N-2-propylcarbamoyl)oxy>methyl>-3-pyrroline 
• 72090-97-2 dimethyl 1-methyl-2-phenyl-3-pyrroline-3,4-dicarboxylate 

Relevant articles and documents

Enantioselective synthesis of α-heteroarylpyrrolidines by copper-catalyzed 1,3-dipolar cycloaddition of α-silylimines

α-Heteroarylpyrrolidines have been efficiently prepared via 1,3-dipolar cycloaddition between silylimines and activated olefins. In the presence of Cu(CH3CN)4PF6/Walphos as catalytic system, high levels of enantioselectivity (up to >99% ee) and diastereoselectivity were achieved (major formation of C-2/C-4 trans-substituted pyrrolidines). The reaction is compatible with a broad variety of dipolarophiles including maleimides, maleates, fumarates, nitroalkenes, and vinylsulfones. The resulting cycloadducts can be transformed into bioactive pyrrolidine derivatives.

Trifluoromethyl-substituted Δ3-imidazolines: Synthesis and reactivity

We describe the preparation of various 4-trifluoromethyl-substituted Δ3-imidazolines, which are precursors to amino acid-derived trifluoromethyl ketones. The imidazolines are prepared from α-silylimines and trifluoroacetonitrile by a 3+2 cycloaddition, and they can be hydrolyzed in weak acid to trifluoromethyl ketones. Additionally, we have identified several ring-opened compounds which result from treatment of the imidazolines with acid or base. Attempts to alkylate the imidazolines led to ring-opened products, so that the alkylation sequence ultimately produced N-alkylated amino acid-derived trifluoromethyl ketones.

A SIMPLE EFFICIENT SYNTHESIS OF 3-PYRROLINES USING A 1,3-DIPOLAR CYCLOADDITION REACTION WITH AN YLIDE GENERATED BY THERMAL DESILYLATION OF AN α-SILYLIMINIUM SALT.

Treatment of N-(benzylidene)trimethylsilylmethylamine with methyl chloroformate at 50 deg C produced an ylide that reacted with dimethyl acetylenedicarboxylate to give dimethyl 1-methoxycarbonyl-2-phenyl-3-pyrroline-3,4-dicarboxylate.