90719-29-2

Basic information

• Product Name: (N-CROTONYL)-(4S)-ISOPROPYL-2-OXAZOLIDINONE
• Synonyms: (N-CROTONYL)-(4S)-ISOPROPYL-2-OXAZOLIDINONE;(4s)-n-crotonyl-4-isopropyl-2-oxazolidinone;(S)-(+)-3-CROTONOYL-4-ISOPROPYL-2-OXAZOLIDINONE;(N-Crotonyl)-(S)-4-benzyl-2-oxazolidinone;(4S)-N-Crotonyl-4-isopropyl-2-oxazolidinone,99%
• CAS NO: 90719-29-2
• Molecular Formula: C₁₀H₁₅NO₃
• Molecular Weight: 197.23
• Product Categories: Peptide
• Mol File: 90719-29-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 55-58 °C
• Boiling Point: 256.5°Cat760mmHg
• Flash Point: 108.9°C
• Appearance: White/Crystals
• Density: 1.112g/cm³
• Vapor Pressure: 0.0153mmHg at 25°C
• Refractive Index: 1.493
• CAS DataBase Reference: (N-CROTONYL)-(4S)-ISOPROPYL-2-OXAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (N-CROTONYL)-(4S)-ISOPROPYL-2-OXAZOLIDINONE(90719-29-2)
• EPA Substance Registry System: (N-CROTONYL)-(4S)-ISOPROPYL-2-OXAZOLIDINONE(90719-29-2)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 90719-29-2(Hazardous Substances Data)

Usage

Chemical Properties

White crystals

InChI:InChI=1/C10H15NO3/c1-4-5-9(12)11-8(7(2)3)6-14-10(11)13/h4-5,7-8H,6H2,1-3H3/b5-4+/t8-/m1/s1

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 90719-29-2 (S)-3-((Z)-But-2-enoyl)-4-isopropyl-oxazolidin-2-one 
• 625-35-4 trans-chrotonyl chloride 
• 17016-83-0 (4S)-4-isopropyl-1,3-oxazolidin-2-one 

Downstream Products

• 155779-80-9 (4S)-3-<(3S)-1-oxo-3-phenylbutyl>-4-(1-methylethyl)-2-oxazolidinone 
• 155779-79-6 (4S)-3-<(3R)-1-oxo-3-phenylbutyl>-4-(1-methylethyl)-2-oxazolidinone 
• 1422767-01-8 (S)-4-isopropyl-3-((3S,4S,5R)-5-methyl-3-phenyl-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl)isoxazolidine-4-carbonyl)oxazolidin-2-one 
• 1422767-02-9 C₂₇H₂₉F₃N₂O₆ 
• 1422766-99-1 (S)-3-((3S,4S,5R)-2-benzhydryl-5-methyl-3-phenylisoxazolidine-4-carbonyl)-4-isopropyloxazolidin-2-one 
• 1422637-24-8 (4S)-isopropyl-3-[(3R)-((4R)-phenyl-2-thioxo-oxazolidin-3-yl)butyryl]oxazolidin-2-one 
• 1429327-65-0 (4S)-isopropyl-3-[(3S)-((4R)-phenyl-2-thioxo-oxazolidin-3-yl)butyryl]oxazolidin-2-one 
• 1422536-97-7 (4S)-isopropyl-3-[(3S)-((4S)-phenyl-2-thioxo-oxazolidin-3-yl)butyryl]oxazolidin-2-one 
• 1197006-77-1 (2'S,2R,3S,4S)-{[3,4-dihydro-4-methyl-2-(4-nitrophenyl)-5-phenyl-2H-pyrrol-3-yl]-carbonyl}-2-oxo-4-isopropyloxazolidine 
• 121425-50-1 (R)-2-{(4R,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-3-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-3-oxo-propionaldehyde 
• 198124-64-0 (S)-3-((S)-2-{(4R,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-but-3-enoyl)-4-isopropyl-oxazolidin-2-one 
• 198124-80-0 (S)-3-[(2S,3R,4R,5R,6R)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-4,6-dimethyl-2-vinyl-heptanoyl]-4-isopropyl-oxazolidin-2-one 
• 462656-83-3 C₂₅H₃₅NO₇ 
• 692749-33-0 (S)-3-[(E)-(2S,3S,6R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-4,6-dimethyl-2-vinyl-hept-4-enoyl]-4-isopropyl-oxazolidin-2-one 

Relevant articles and documents

Nucleophilic halo-michael addition under lewis-base activation

A simple and general conjugate nucleophilic halogenation is presented. The THTO/halosilane combination has shown the ability to act as a nucleophilic halide source in the conjugate addition to a variety of Michael acceptors. In addition, a straightforward diastereoselective halogen installation using α,β-unsaturated acyloxazolidinones as platforms has been developed.

SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one

The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels-Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions. The Royal Society of Chemistry 2006.