90319-52-1

Basic information

• Product Name: (R)-(-)-4-Phenyl-2-oxazolidinone
• Synonyms: 2-OXAZOLIDINONE, 4-PHENYL-, (4R)-;(4R)-4-PHENYLOXAZOLIDIN-2-ONE;(4R)-4-PHENYL-1,3-OXAZOLIDIN-2-ONE;(4R)-PHENYL-2-OXAZOLIDINONE;(R)-(-)-4-PHENYL-2-OXAZOLIDINONE;(R)-(+)-4-PHENYL-2-OXAZOLIDINONE;(R)-4-PHENYL-2-OXAZOLIDINONE;S/R-4-BENZYL-2-OXAZOLIDINONE
• CAS NO: 90319-52-1
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17
• EINECS: 1312995-182-4
• Product Categories: Oxazolidinone;Isoxazoles, Oxadiazoles, Oxazoles;chiral;Chiral Reagent;Aromatics Compounds;Asymmetric Synthesis;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry;Chiral chemicals;Peptide;Aromatics;Heterocycles;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 90319-52-1.mol
• Article Data: 83

Chemical Properties

• Melting Point: 131-133 °C(lit.)
• Boiling Point: 290.25°C (rough estimate)
• Flash Point: 199.953 °C
• Appearance: white to light yellow crystal powder
• Density: 1.2021 (rough estimate)
• Vapor Pressure: 7.79E-07mmHg at 25°C
• Refractive Index: -72 ° (C=1, AcOEt)
• Storage Temp.: Store at 0-5°C
• Solubility: Chloroform (Slightly), Ethyl Acetate, Methanol (Slightly)
• PKA: 12.05±0.40(Predicted)
• BRN: 4308995
• CAS DataBase Reference: (R)-(-)-4-Phenyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-4-Phenyl-2-oxazolidinone(90319-52-1)
• EPA Substance Registry System: (R)-(-)-4-Phenyl-2-oxazolidinone(90319-52-1)

Safety Data

• Hazard Codes: F+,Xi
• Statements: 12-36
• Safety Statements: 22-24/25-33-26-16-7/9
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 90319-52-1(Hazardous Substances Data)

Usage

Description

(R)-(-)-4-Phenyl-2-oxazolidinone, with the CAS number 90319-52-1, is a chiral heterocyclic compound that plays a significant role in organic synthesis. It is characterized by its unique structure, which includes a phenyl group attached to a 2-oxazolidinone ring. (R)-(-)-4-Phenyl-2-oxazolidinone is known for its potential applications in the synthesis of various biologically active molecules, making it a valuable building block in the field of organic chemistry.

Uses

Used in Pharmaceutical Industry:
(R)-(-)-4-Phenyl-2-oxazolidinone is used as a synthon for the synthesis of α-amino acids and β-lactam antibiotics. Its chiral nature and unique structural features make it an ideal candidate for the development of enantioselective synthetic routes to these important classes of compounds.
Used in Organic Synthesis:
(R)-(-)-4-Phenyl-2-oxazolidinone is used as a versatile building block in organic synthesis. Its ability to form stable intermediates and participate in various chemical reactions allows chemists to use it in the construction of complex organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in α-amino acid synthesis:
(R)-(-)-4-Phenyl-2-oxazolidinone is employed as a key intermediate in the synthesis of α-amino acids, which are essential building blocks for the formation of proteins and peptides. Its use in this application allows for the development of novel synthetic routes to enantiomerically pure α-amino acids, which are crucial for the production of biologically active peptides and proteins.
Used in β-lactam antibiotic preparation:
(R)-(-)-4-Phenyl-2-oxazolidinone is also used in the preparation of β-lactam antibiotics, a widely used class of antibiotics that includes penicillins, cephalosporins, and carbapenems. Its incorporation into the synthesis of these antibiotics can lead to the development of new, more effective, and potentially more selective β-lactam-based drugs.

InChI:InChI=1/C9H9NO2/c11-9-10-8(6-12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,10,11)/t8-/m0/s1

Upstream product

• 56613-80-0 D-2-phenylglycinol 
• 503-38-8 trichloromethyl chloroformate 
• 616-38-6 carbonic acid dimethyl ester 
• 20989-17-7 Phenylglycinol 
• 57-13-6 urea 
• 52724-28-4 bis(tetraethylammonium) carbonate 
• 124-38-9 carbon dioxide 
• 75-03-6 ethyl iodide 
• 201300-96-1 (4'R)-2-bromo-1-(2'-oxo-4'-phenyloxazolidin-3'-yl)propan-1-one 
• 869111-27-3 phenethyl tosyloxycarbamate 
• 86217-38-1 4-phenyl-2-oxazolidinone 
• 97-72-3 2-Methylpropionic anhydride 
• 123-62-6 propionic acid anhydride 
• 1044204-03-6 (S,R)-4-phenyl-3-(2-methoxy-2-phenyl-2-trifluoromethyl-acetyl)oxazolidin-2-one 

Downstream Products

• 201300-96-1 (4'R)-2-bromo-1-(2'-oxo-4'-phenyloxazolidin-3'-yl)propan-1-one 
• 148766-15-8 (R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one 
• 99333-53-6 ((R)-2-Oxo-4-phenyl-oxazolidin-3-yl)-acetic acid ethyl ester 
• 189350-20-7 (R)-3-((R)-2-Methyl-1-nitromethyl-propyl)-4-phenyl-oxazolidin-2-one 
• 189350-22-9 (R)-3-((R)-2,2-Dimethyl-1-nitromethyl-propyl)-4-phenyl-oxazolidin-2-one 
• 155835-37-3 (4R)-3-(3-phenyl-2-(E)-propenoyl)-4-phenyl-2-oxazolidinone 
• 194031-58-8 (4R,2E)-3-(1-oxo-2-isohexenyl)-4-phenyl-2-oxazolidinone 
• 161745-73-9 (4R)-3-phenylacetyl-4-phenyl-1,3-oxazolidin-2-one 
• 206068-68-0 (R)-3-((S)-2-Benzyloxy-1-nitromethyl-ethyl)-4-phenyl-oxazolidin-2-one 
• 189350-19-4 (R)-3-((R)-1-Nitromethyl-butyl)-4-phenyl-oxazolidin-2-one 
• 258341-28-5 (4R)-3-(8-octen-2-ynoyl)-4-phenyloxazolidin-2-one 
• 258341-30-9 (4R)-3-(8-nonen-2-ynoyl)-4-phenyloxazolidin-2-one 
• 269401-91-4 N-(2'-bromoethyl)-(R)-4-phenyl-2-oxazolidinone 
• 160695-26-1 (4R)-3-propionyl-4-phenyl-1,3-oxazolidin-2-one 

Relevant articles and documents

Catalytic enantioselective synthesis of β-amino alcohols by nitrene insertion

Chiral β-amino alcohols are important building blocks for the synthesis of drugs, natural products, chiral auxiliaries, chiral ligands and chiral organocatalysts. The catalytic asymmetric β-amination of alcohols offers a direct strategy to access this class of molecules. Herein, we report a general intramolecular C(sp3)-H nitrene insertion method for the synthesis of chiral oxazolidin-2-ones as precursors of chiral β-amino alcohols. Specifically, the ring-closing C(sp3)-H amination of N-benzoyloxycarbamates with 2 mol% of a chiral ruthenium catalyst provides cyclic carbamates in up to 99% yield and with up to 99% ee. The method is applicable to benzylic, allylic, and propargylic C-H bonds and can even be applied to completely non-activated C (sp3)-H bonds, although with somewhat reduced yields and stereoselectivities. The obtained cyclic carbamates can subsequently be hydrolyzed to obtain chiral β-amino alcohols. The method is very practical as the catalyst can be easily synthesized on a gram scale and can be recycled after the reaction for further use. The synthetic value of the new method is demonstrated with the asymmetric synthesis of a chiral oxazolidin-2-one as intermediate for the synthesis of the natural product aurantioclavine and chiral β-amino alcohols that are intermediates for the synthesis of chiral amino acids, indane-derived chiral Box-ligands, and the natural products dihydrohamacanthin A and dragmacidin A.[Figure not available: see fulltext.].

Chiral separation materials based on derivatives of 6-amino-6-deoxyamylose

In order to develop new type of chiral separation materials, in this study, 6-amino-6-deoxyamylose was used as chiral starting material with which 10 derivatives were synthesized. The amino group in 6-amino-6-deoxyamylose was selectively acylated and then the hydroxyl groups were carbamoylated yielding amylose 6-amido-6-deoxy-2,3-bis(phenylcarbamate)s, which were employed as chiral selectors (CSs) for chiral stationary phases of high-performance liquid chromatography. The resulted 6-amido-6-deoxyamyloses and amylose 6-amido-6-deoxy-2,3-bis(phenylcarbamate)s were characterized by IR, 1H NMR, and elemental analysis. Enantioseparation evaluations indicated that most of the CSs demonstrated a moderate chiral recognition capability. The 6-nonphenyl (6-nonPh) CS of amylose 6-cyclohexylformamido-6-deoxy-2,3-bis(3,5-dimethylphenylcarbamate) showed the highest enantioselectivity towards the tested chiral analytes; the phenyl-heterogeneous (Ph-hetero) CS of amylose 6-(4-methylbenzamido)-6-deoxy-2,3-bis(3,5-dimethylphenylcarbamate) baseline separated the most chiral analytes; the phenyl-homogeneous (Ph-homo) CS of amylose 6-(3,5-dimethylbenzamido)-6-deoxy-2,3-bis(3,5-dimethylphenylcarbamate) also exhibited a good enantioseparation capability among the developed CSs. Regarding Ph-hetero CSs, the enantioselectivity depended on the combination of the substituent at 6-position and that at 2- and 3-positions; as for Ph-homo CSs, the enantioselectivity was related to the substituent at 2-, 3-, and 6-positions; with respect to 6-nonPh CSs, the retention factor of most analytes on the corresponding CSPs was lower than that on Ph-hetero and Ph-homo CSPs in the same mobile phases, indicating π–π interactions did occur during enantioseparation. Although the substituent at 6-position could not provide π–π interactions, the 6-nonPh CSs demonstrated an equivalent or even higher enantioselectivity compared with the Ph-homo and Ph-hetero CSs.

Synthesis of Chiral 5-Aryl-2-oxazolidinones via Halohydrin Dehalogenase-Catalyzed Enantio- and Regioselective Ring-Opening of Styrene Oxides

An efficient biocatalytic approach for enantio- and regioselective ring-opening of styrene oxides with cyanate was developed by using the halohydrin dehalogenase HheC from Agrobacterium radiobacter AD1, generating the corresponding chiral 5-aryl-2-oxazoli