145588-95-0

Basic information

• Product Name: (S)-4-Benzyl-3-propionyl-1,3-oxazolidine-2-thione
• Synonyms: (S)-4-BENZYL-3-PROPIONYL-1,3-OXAZOLIDINE-2-THIONE;1-[(4S)-4-(phenylMethyl)-2-thioxo-3-oxazolidinyl]-1-Propanone;1-Propanone,1-[(4S)-4-(phenylmethyl)-2-thioxo-3-oxazolidinyl]-;1-[(4S)-4-(Phenylmethyl)-2-thioxo-3-oxazolidinyl]-1-prop anone,99%e.e.;(S)-4-Benzyl-3-Propionyl-1,3-Oxazolidine-2-Thione(WX619934)
• CAS NO: 145588-95-0
• Molecular Formula: C₁₃H₁₅NO₂S
• Molecular Weight: 249.33
• Mol File: 145588-95-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 74-75 °C
• Boiling Point: 346.612 °C at 760 mmHg
• Flash Point: 163.426 °C
• Appearance: /
• Density: 1.234 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.609
• CAS DataBase Reference: (S)-4-Benzyl-3-propionyl-1,3-oxazolidine-2-thione(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-Benzyl-3-propionyl-1,3-oxazolidine-2-thione(145588-95-0)
• EPA Substance Registry System: (S)-4-Benzyl-3-propionyl-1,3-oxazolidine-2-thione(145588-95-0)

Safety Data

• Hazardous Substances Data: 145588-95-0(Hazardous Substances Data)

Usage

General Description

(S)-4-Benzyl-3-propionyl-1,3-oxazolidine-2-thione is a chemical compound with the molecular formula C13H15NOS. It is a heterocyclic organic compound with a five-membered ring containing nitrogen, oxygen, and sulfur atoms. (S)-4-Benzyl-3-propionyl-1,3-oxazolidine-2-thione is used in the pharmaceutical industry for its potential medicinal properties, including antimicrobial and antifungal activities. It has also been studied for its potential use in the development of new drugs for the treatment of various diseases. Additionally, it may have applications in the synthesis of other organic compounds and as a reagent in chemical reactions. The exact mode of action and specific uses of this compound are still under investigation, making it an area of ongoing research and interest in the scientific community.

InChI:InChI=1/C13H15NO2S/c1-2-12(15)14-11(9-16-13(14)17)8-10-6-4-3-5-7-10/h3-7,11H,2,8-9H2,1H3/t11-/m0/s1

Upstream product

• 79-03-8 propionyl chloride 
• 131744-19-9 (4S)-4-benzyl-1,3-oxazolidine-2-thione 
• 123-62-6 propionic acid anhydride 
• 3182-95-4 L-Phenylalaninol 

Downstream Products

• 145588-96-1 3<4S,(Z)>-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-propenyl>-4-(1-methylphenyl)-2-oxazolidinethione 
• 194019-83-5 (4S)-3-[(2S,3R)-3-hydroxy-2,4-dimethyl-1-oxopentyl]-4-benzyl-1,3-oxazolidine-2-thione 
• 213740-08-0 (2S,3R,4S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-hexan-1-one 
• 213740-09-1 (2S,3R,4R,5R,6S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4,6-trimethyl-octan-1-one 
• 329362-91-6 (2R,3S,4E)-1-[4-benzyl-2-thioxo-(4S)-1,3-oxazolan-3-yl]-3-hydroxy-2-methyl-5-phenylpent-4-en-1-one 
• 363610-59-7 (2R,3S,4S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentan-1-one 
• 438625-73-1 (2S,3S)-4-[(2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-butane-1,3-diol 
• 634204-37-8 (E)-(2R,3R)-7-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-hept-4-en-1-one 

Relevant articles and documents

Asymmetric aldol additions: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones

Asymmetric aldol additions using chlorotitanium enolates of N-acyloxazolidinone, oxazolidinethione, and thiazolidinethione propionates proceed with high diastereoselectivity for the Evans or non-Evans syn product depending on the nature and amount of the base used. With 1 equiv of titanium tetrachloride and 2 equiv of (-)-sparteine as the base or 1 equiv of (-)-sparteine and 1 equiv of N-methyl-2-pyrrolidinone, selectivities of 97:3 to >99:1 were obtained for the Evans syn aldol products using N-propionyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones. The non-Evans syn aldol adducts are available with the oxazolidinethione and thiazolidinethiones by altering the Lewis acid/amine base ratios. The change in facial selectivity in the aldol additions is proposed to be a result of switching of mechanistic pathways between chelated and nonchelated transition states. The auxiliaries can be reductively removed or cleaved by nucleophilic acyl substitution. Iterative aldol sequences with high diastereoselectivity can also be accomplished.

Synthesis of optically active α-phenylselenyl carbonyl derivatives

Homochiral silyl enol ethers derived from N-acyl oxazolidinones can be phenyselenylated in high diastereoselectivity and good yield with phenylselenyl chloride. Removal of the chiral auxiliary is accompanied by some epimerisation, leading to isolation of