438496-21-0

Basic information

• Product Name: Benzenepropanamide, N-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-
• CAS NO: 438496-21-0
• Molecular Formula: C14H21NO2
• Molecular Weight: 235.326
• Mol File: 438496-21-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzenepropanamide, N-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanamide, N-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-(438496-21-0)
• EPA Substance Registry System: Benzenepropanamide, N-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-(438496-21-0)

Safety Data

• Hazardous Substances Data: 438496-21-0(Hazardous Substances Data)

Upstream product

• 2026-48-4 (S)-valinol 
• 501-52-0 3-Phenylpropionic acid 
• 104-53-0 3-phenyl-propionaldehyde 
• 645-45-4 hydrocinnamic acid chloride 

Downstream Products

• 93684-44-7 (S)-(-)-4,5-dihydro-4-(1-methylethyl)-2-(2-phenylethyl)oxazole 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 17016-83-0 (4S)-4-isopropyl-1,3-oxazolidin-2-one 

Relevant articles and documents

Phosphorus-Based Organocatalysis for the Dehydrative Cyclization of N-(2-Hydroxyethyl)amides into 2-Oxazolines

A metal-free, biomimetic catalytic protocol for the cyclization of N-(2-hydroxyethyl)amides to the corresponding 2-oxazolines (4,5-dihydrooxazoles), promoted by the 1,3,5,2,4,6-triazatriphosphorine (TAP)-derived organocatalyst tris(o-phenylenedioxy)cyclotriphosphazene (TAP-1) has been developed. This approach requires less precatalyst compared to the reported relevant systems, with respect to the phosphorus atom (the maximum turnover number (TON) ～30), and exhibits a broader substrate scope and higher functional-group tolerance, providing the functionalized 2-oxazolines with retention of the configuration at the C(4) stereogenic center of the 2-oxazolines. Widely accessible β-amino alcohols can be used in this approach, and the cyclization of N-(2-hydroxyethyl)amides provides the desired 2-oxazolines in up to 99% yield. The mechanism of the reaction was studied by monitoring the reaction using spectral and analytical methods, whereby an 18O-labeling experiment furnished valuable insights. The initial step involves a stoichiometric reaction between the substrate and TAP-1, which leads to the in situ generation of the catalyst, a catechol cyclic phosphate, as well as to a pyrocatechol phosphate and two possible active intermediates. The dehydrative cyclization was also successfully conducted on the gram scale.

A simple method removing 2-oxazolidinone and 2-hydroxyethylamine auxiliaries in methoxide-carbonate systems for synthesis of planar-chiral nicotinate

A facile and practical removal of 2-oxazolidinone and 2-hydroxyethylamine auxiliaries was accomplished by treating the corresponding N-acyl-2-oxazolidinone and N-(2-hydroxyethyl)amide derivatives in simple methoxide-carbonate systems. The presence of excess DMC (dimethyl carbonate) accelerates the N-acyl bond cleavage for those substrates under mild reaction conditions, and the present method was found to be useful especially for the synthesis of planar-chiral nicotinate.