950829-01-3

Basic information

• Product Name: (1S)-N-(4-methoxyphenyl)-1-phenyl-2-{2-[(S)-p-tolylsulfinyl]phenyl}ethylamine
• Synonyms: (1S)-N-(4-methoxyphenyl)-1-phenyl-2-{2-[(S)-p-tolylsulfinyl]phenyl}ethylamine
• CAS NO: 950829-01-3
• Molecular Weight: 441.594
• Mol File: 950829-01-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S)-N-(4-methoxyphenyl)-1-phenyl-2-{2-[(S)-p-tolylsulfinyl]phenyl}ethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-N-(4-methoxyphenyl)-1-phenyl-2-{2-[(S)-p-tolylsulfinyl]phenyl}ethylamine(950829-01-3)
• EPA Substance Registry System: (1S)-N-(4-methoxyphenyl)-1-phenyl-2-{2-[(S)-p-tolylsulfinyl]phenyl}ethylamine(950829-01-3)

Safety Data

• Hazardous Substances Data: 950829-01-3(Hazardous Substances Data)

Upstream product

• 10381-68-7 (S)-2-methyl-1-(p-tolylsulfinyl)benzene 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 104-94-9 4-methoxy-aniline 
• 100-52-7 benzaldehyde 

Downstream Products

• 503819-33-8 (1S)-1-phenyl-2-[(S)-2-(p-toluenesulfinyl)phenyl]ethylamine 
• 3082-58-4 (S)-1,2-diphenylethyl amine 

Relevant articles and documents

π-π Stacking versus steric effects in stereoselectivity control: Highly diastereoselective synthesis of syn-1,2-diarpropylamines

N-Arylarylideneamines react with sulfinylbenzyl carbanions derived from 2-(p-tolylsulfinyl)toluenes (S)-1 and (S)-2, affording epimeric mixtures at C1 of 1,2-diarylethyl- and 1,2-diarylpropylamine derivatives. The sulfinyl group completely controls the configuration at C2 in the reactions of (S)-2. The configuration at Cl depends on the electron density of the ring adjacent to the iminic carbon atom which is modulated by π-π stacking interactions with the ring joined to the carbanionic centre. The stereoselectivity was controlled by modifying the acceptor character of the arylideneamine ring with appropriate substituents, the formation of the highly selective (R) configuration at C1 being made possible by electron-donating groups. N-(2,4,6-Trimethoxyphenyl) arylideneamines have been shown to be suitable starting materials for the preparation of (R)-1,2-diarylethyl- and (1R,2S)-1,2-diarylpropylamines (syn epimers) in a highly stereoselective manner.