184178-55-0

Basic information

• Product Name: (S)-N-(1-phenylethyl)-(R)-2-phenoxypropionamide
• CAS NO: 184178-55-0
• Molecular Weight: 269.343
• Mol File: 184178-55-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-N-(1-phenylethyl)-(R)-2-phenoxypropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-(1-phenylethyl)-(R)-2-phenoxypropionamide(184178-55-0)
• EPA Substance Registry System: (S)-N-(1-phenylethyl)-(R)-2-phenoxypropionamide(184178-55-0)

Safety Data

• Hazardous Substances Data: 184178-55-0(Hazardous Substances Data)

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 1129-46-0 (R)-(+)-2-phenoxypropionic acid 
• 940-31-8 2-phenoxypropionic acid 
• 2627-86-3 (-)-α-methylbenzylamine 

Downstream Products

• 1129-46-0 (R)-(+)-2-phenoxypropionic acid 
• 940-31-8 (+)-2-(phenoxy)propionic acid 

Relevant articles and documents

Resolution of (±)-mandelic- and (±)-2-(chiorophenoxy)propionic-acid derivatives by crystallization of their diastereomeric amides with (R)- or (S)-α-arylethylamines

An alternative and cost effective route for the resolution in high ees (95-99%) of (±)-mandelic-and (±)-2-(chlorophenoxy)propionic- acid derivatives is reported. The key step involves the covalent derivatization and separation of their diastereomeric amides with (R)- or (S)-α- arylethylamines.

Determination of the absolute configuration of amines and α-amino acids by 1H NMR of (R)-O-aryllactic acid amides

(R)-O-Aryllactic acid (ROAL) amides derived from α-chiral primary amines and α-amino acid esters show different chemical shifts in 1H NMR spectroscopy (300 MHz) depending on their configuration. Molecular mechanics, semiempirical calculations, and 1H NMR studies suggest that, in solution, these amides prefer an ap-Z conformation with the CαOAr and C=O groups close to anti-periplanar as in the case of mandelic acid amides. The proposed conformational preference is different from that of the ROAL esters (CαH and C=O groups in a syn-periplanar conformation). The conformational model for ROAL amides allows the absolute configuration assignment of primary amines and α-amino acid esters according to the relative position of the aryl group and the substituents on the amine moiety, and also their enantiomeric composition.