32851-51-7

Basic information

• Product Name: Benzenemethanamine, N-(3,4-dihydro-1(2H)-naphthalenylidene)-
• CAS NO: 32851-51-7
• Molecular Formula: C17H17N
• Molecular Weight: 235.329
• Mol File: 32851-51-7.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: Benzenemethanamine, N-(3,4-dihydro-1(2H)-naphthalenylidene)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanamine, N-(3,4-dihydro-1(2H)-naphthalenylidene)-(32851-51-7)
• EPA Substance Registry System: Benzenemethanamine, N-(3,4-dihydro-1(2H)-naphthalenylidene)-(32851-51-7)

Safety Data

• Hazardous Substances Data: 32851-51-7(Hazardous Substances Data)

Upstream product

• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 100-46-9 benzylamine 
• 529-33-9 1,2,3,4-Tetrahydro-1-naphthol 
• 100-47-0 benzonitrile 

Downstream Products

• 92885-62-6 anti-2'-benzyl-1,2,3,4-tetrahydronaphthalene-1-spiro-3'-oxaziridine 
• 212250-85-6 N-benzyl-1,2,3,4-tetrahydronaphthalen-1-amine 
• 124985-44-0 C₂₄H₁₉NO 
• 124985-46-2 C₂₄H₁₉NO 
• 1176778-10-1 C₂₅H₂₁NO₂ 
• 129574-23-8 C₂₅H₂₃NO 
• 129574-22-7 C₂₄H₂₁NO 
• 24381-34-8 (4bR,10bS)-5-Benzyl-4b,10b,11,12-tetrahydro-5H-benzo[c]phenanthridin-6-one 
• 51066-28-5 5-benzyl-11,12-dihydrobenzophenanthridin-6(5H)-one 
• 129574-18-1 N-Benzyl-2-bromo-N-(3,4-dihydro-naphthalen-1-yl)-benzamide 
• 124985-32-6 N-benzyl-N-(1,2-dihydronaphth-4-yl)-2-iodobenzamide 

Relevant articles and documents

Evaluating dynamic kinetic resolution strategies in the asymmetric hydrosilylation of cyclic ketimines

Attempts at performing dynamic kinetic resolution on a series of cyclic ketimines by making use of an asymmetric organocatalysed hydrosilylation gave modest conversion and moderate to good enantioselectivities. In the case of α-tetralone derivatives, the use of an N-benzyl protecting group was found to be crucial in obtaining enhanced levels of selectivity.

Asymmetric hydrogenation of N-alkyl and N-aryl ketimines using chiral cationic Ru(diamine) complexes as catalysts: The counteranion and solvent effects, and substrate scope

Asymmetric hydrogenation of N-alkyl and N-aryl ketimines catalyzed by chiral cationic η6-arene-(N-monosulfonylated diamine) Ru(II) complexes has been investigated. Strong counteranion and solvent effects on the enantioselectivity were observed. The ruthenium catalyst bearing non-coordinating BArF- anion was found to be particularly effective for the hydrogenation of acyclic and exocyclic N-alkyl ketimines in the presence of (Boc)2O in dichloromethane or even under solvent-free conditions, providing chiral amines with up to >99% ee and full conversions. Alternatively, the ruthenium catalyst bearing achiral phosphate anion together with corresponding phosphoric acid as the additive was also efficient for the hydrogenation of N-alkyl ketimines in the absence of (Boc)2O with excellent enantioselectivities and full conversions. For N-aryl ketimines lower enantiomeric excesses were observed by using the ruthenium catalyst bearing BArF- anion. This catalytic protocol thus provides a facile and practical access to optically active amines and has been successfully employed in the gram-scale synthesis of enantiomerically pure (+)-sertraline.

Asymmetric hydrogenation of N-Alkyl ketimines with phosphine-free, chiral, cationic Ru-MsDPEN catalysts

(Solvent) free and easy: A phosphine-free, chiral, cationic Ru-MsDPEN complex [(S,S)-1] is found to be an efficient catalyst for the enantioselective hydrogenation of a range of often-problematic N-alkyl ketimines (see scheme). This new method provides a more practical and greener synthetic approach to optically active amines, particularly N-alkyl amines, such as Sertraline.