159213-03-3

Basic information

• Product Name: (1S 2S)-(+)-PSEUDOEPHEDRINEPROPIONAMIDE&
• Synonyms: Propanamide,N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl-, [S-(R*,R*)]-; N-[(1S,2S)-2-Hydroxy-1-methyl-2-phenylethyl]-N-methylpropanamide
• CAS NO: 159213-03-3
• Molecular Formula: C₁₃H₁₉NO₂
• Molecular Weight: 221.3
• Product Categories: Asymmetric Synthesis;Chiral Auxiliaries;Ephedrine Derivatives
• Mol File: 159213-03-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 114-118 °C(lit.)
• Boiling Point: 374.1°Cat760mmHg
• Flash Point: 180.1°C
• Appearance: /
• Density: 1.065g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.53
• PKA: 13.70±0.20(Predicted)
• CAS DataBase Reference: (1S 2S)-(+)-PSEUDOEPHEDRINEPROPIONAMIDE&(CAS DataBase Reference)
• NIST Chemistry Reference: (1S 2S)-(+)-PSEUDOEPHEDRINEPROPIONAMIDE&(159213-03-3)
• EPA Substance Registry System: (1S 2S)-(+)-PSEUDOEPHEDRINEPROPIONAMIDE&(159213-03-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 159213-03-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H19NO2/c1-4-12(15)14(3)10(2)13(16)11-8-6-5-7-9-11/h5-10,13,16H,4H2,1-3H3/t10-,13+/m0/s1

Upstream product

• 90-82-4 pseudoephedrine 
• 79-03-8 propionyl chloride 
• 123-62-6 propionic acid anhydride 
• 554-12-1 propanoic acid methyl ester 

Downstream Products

• 159345-07-0 (2R)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethylhexanamide 
• 159345-06-9 (2R)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethyl-3-phenylpropionamide 
• 192060-47-2 (2R,4S)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylhexanamide 
• 192060-46-1 [1S,2S(R)]-N-(2-hydroxy-1-methyl-2-phenylethyl)-N,2-dimethylpentionamide 
• 249745-79-7 (2R,4S)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N,2,4-trimethyloctanamide 
• 219783-12-7 [2R,3S,1'S,2'S]-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-butanamide 
• 1094537-98-0 (2R)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-2-methyl-5-phenylpentanoic acid methylamide 
• 1068601-03-5 (R)-N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N,2'-dimethylpent-4-enamide 
• 1025936-02-0 (1'S,2'S,2R)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3-methoxybenzyl)propionamide 
• 859844-95-4 (R)-7-(4-Methoxy-benzyloxy)-2-methyl-heptanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 866923-94-6 (2R,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide 
• 795306-42-2 (2R,4S,5S)-6-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-hept-6-enoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 791131-39-0 6-(tert-butyl-diphenyl-silanyloxy)-3-methyl-hexan-2-one 
• 717910-21-9 (2S,4S)-7-(4-Methoxy-benzyloxy)-2,4-dimethyl-heptan-1-ol 

Relevant articles and documents

Enantioselective synthesis and determination of the absolute configuration of the male sex pheromone of the parasitoid wasp: Urolepis rufipes

Males of the parasitoid wasp Urolepis rufipes use 2,6-dimethyl-7-octene-1,6-diol as a sex pheromone to attract virgin females. Herein, we determine the absolute configuration of the pheromone to be (2S,6S)-2,6-dimethyl-7-octene-1,6-diol (2S,6S-6) and present a stereoselective synthesis of the natural enantiomer of this new linalool derivative. In addition, we show that female wasps respond to the natural 2S,6S-6 stereoisomer while 2R,6S-6 is behaviorally inactive.

Enyne metathesis approach towards the cyclopentane motif of jatrophane diterpenes

A short and efficient synthesis of the cyclopentane moiety of the jatrophane diterpene Pl-3 has been developed. The route features an enyne metathesis reaction, and a stereoselective palladium-catalyzed reductive epoxide opening as key steps. Georg Thieme Verlag Stuttgart New York.

General synthesis of highly functionalized cyclopentane segments for the preparation of jatrophane diterpenes

Short and efficient syntheses of two diastereomeric cyclopentane segments present in most jatrophane diterpenes were achieved. Key steps are a stereoselective C-2 elongation, an RCM, and a hydroboration reaction. An orthogonal protecting group methodology