39663-75-7

Basic information

• Product Name: (+/-)-cis-4-methyl-5-phenyloxazolidin-2-one
• Synonyms: (+/-)-cis-4-methyl-5-phenyloxazolidin-2-one
• CAS NO: 39663-75-7
• Molecular Weight: 177.203
• Mol File: 39663-75-7.mol
• Article Data: 39

Chemical Properties

• CAS DataBase Reference: (+/-)-cis-4-methyl-5-phenyloxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-cis-4-methyl-5-phenyloxazolidin-2-one(39663-75-7)
• EPA Substance Registry System: (+/-)-cis-4-methyl-5-phenyloxazolidin-2-one(39663-75-7)

Safety Data

• Hazardous Substances Data: 39663-75-7(Hazardous Substances Data)

Usage

General Description

(+/-)-cis-4-methyl-5-phenyloxazolidin-2-one is a chemical compound with the molecular formula C10H11NO2. It is a chiral molecule, meaning it has two mirror image forms, and is used as a chiral auxiliary in asymmetric synthesis. (+/-)-cis-4-methyl-5-phenyloxazolidin-2-one is often used in organic chemistry as a building block for the synthesis of various pharmaceuticals and natural products. It can also be used as a catalyst in certain reactions, as well as a precursor for the preparation of other chiral compounds. Its unique structure and properties make it a valuable tool in synthetic chemistry for the creation of new and diverse molecules with specific biological activities or other desired properties.

Upstream product

• 99056-06-1 C₁₀H₁₁N₃O₂ 
• 14838-15-4 u-2-amino-1-phenylpropan-1-ol 
• 105-58-8 Diethyl carbonate 
• 59050-74-7 cis-4-methyl-5-phenyl-1,3-oxazolidine-2-thione 
• 79297-23-7 (1R,2S)-2-<(ethoxycarbonyl)amino>-1-phenyl-1-propanol 
• 492-41-1 (1R,2S)-norephedrine 
• 530-62-1 1,1'-carbonyldiimidazole 
• 191043-26-2 (4S,5R)-4-methyl-5-phenyl-1,3-oxazolidine-2-thione 
• 102-92-1 Cinnamoyl chloride 
• 20061-46-5 2-methyl-1,3-benzothiazole-5-carbaldehyde 
• 558-37-2 tert-butylethylene 
• 1158807-35-2 (4S,5R)-3-(diethoxymethyl)-4-imethyl-5-phenyloxazolidin-2-one 
• 76549-03-6 methyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate 
• 76549-02-5 (-)-(2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoic acid 

Downstream Products

• 54680-46-5 norephedrine 
• 14838-15-4 u-2-amino-1-phenylpropan-1-ol 
• 90-81-3 ephedrine 
• 177031-10-6 (4S,5R)-3-(3-Carboxypropanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one 
• 202932-15-8 (4S,5R)-3-[2-(4-Benzyloxy-phenyl)-acetyl]-4-methyl-5-phenyl-oxazolidin-2-one 
• 311804-05-4 (4S,5R)-3-(3-Furan-2-yl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 198344-47-7 (4R,5S)-4-methyl-5-phenyl-3-[(2R)-2-phenylpropionyl]oxazolidin-2-one 
• 4830-43-7 (1RS,2RS)-2-isopropylamino-1-phenyl-propan-1-ol 
• 185210-03-1 (4S,5R)-3-(2-(4-Phenoxyphenyl)acetyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one 
• 1158807-35-2 (4S,5R)-3-(diethoxymethyl)-4-imethyl-5-phenyloxazolidin-2-one 
• 1182351-03-6 {5-[4-bromo-2-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-phenoxy]-2-chloro-phenyl}-acetic acid 
• 1182351-09-2 {5-[4-bromo-2-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-phenoxy]-2-chloro-phenyl}-acetic acid ethyl ester 
• 849488-10-4 (4R,5S)-3-[3-(2,4-difluoro-phenyl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one 
• 849487-89-4 (4S,5R)-(-)-4-methyl-3-pentanoyl-5-phenyl-2-oxazolidinone 

Relevant articles and documents

Enantioconvergent Cu-Catalyzed Radical C-N Coupling of Racemic Secondary Alkyl Halides to Access α-Chiral Primary Amines

α-Chiral alkyl primary amines are virtually universal synthetic precursors for all other α-chiral N-containing compounds ubiquitous in biological, pharmaceutical, and material sciences. The enantioselective amination of common alkyl halides with ammonia is appealing for potential rapid access to α-chiral primary amines, but has hitherto remained rare due to the multifaceted difficulties in using ammonia and the underdeveloped C(sp3)-N coupling. Here we demonstrate sulfoximines as excellent ammonia surrogates for enantioconvergent radical C-N coupling with diverse racemic secondary alkyl halides (>60 examples) by copper catalysis under mild thermal conditions. The reaction efficiently provides highly enantioenrichedN-alkyl sulfoximines (up to 99% yield and >99% ee) featuring secondary benzyl, propargyl, α-carbonyl alkyl, and α-cyano alkyl stereocenters. In addition, we have converted the masked α-chiral primary amines thus obtained to various synthetic building blocks, ligands, and drugs possessing α-chiral N-functionalities, such as carbamate, carboxylamide, secondary and tertiary amine, and oxazoline, with commonly seen α-substitution patterns. These results shine light on the potential of enantioconvergent radical cross-coupling as a general chiral carbon-heteroatom formation strategy.

A new type of L-Tertiary leucine-derived ligand: Synthesis and application in Cu(II)-catalyzed asymmetric Henry reactions

A new series of Schiff bases derived from amino acids were developed as chiral ligands for Cu(II)-catalyzed asymmetric Henry reactions. The optimum ligand 7d exhibited outstanding catalytic efficiency in the Cu(II)-catalyzed asymmetric Henry additions of four nitroalkanes to different kinds of aldehydes to produce 76 desired adducts in high yields (up to 96%) with excellent enantioselectivities, up to 99% enantiomeric excess (ee).

Chiral 1,3,2-Diazaphospholenes as Catalytic Molecular Hydrides for Enantioselective Conjugate Reductions

Secondary 1,3,2-diazaphospholenes have a polarized P?H bond and are emerging as molecular hydrides. Herein, a class of chiral, conformationally restricted methoxy-1,3,2-diazaphospholene catalysts is reported. We demonstrate their catalytic potential in asymmetric 1,4-reductions of α,β-unsaturated carbonyl derivatives, including enones, acyl pyrroles, and amides, which proceeded in enantioselectivities of up to 95.5:4.5 e.r.