160695-26-1

Basic information

• Product Name: (R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE
• Synonyms: (R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE;R-(+)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE;(4R)-4-phenyl-3-propanoyl-1,3-oxazolidin-2-one;(R)-4-Phenyl-3-propionyl-2-oxazolidinone, ee: 97%;(R)-4-Phenyl-3-propionyl-2-oxazolidinone,99%e.e.;(4R)-4-Phenyl-3-Propionyl-1,3-Oxazolidin-2-One
• CAS NO: 160695-26-1
• Molecular Formula: C₁₂H₁₃NO₃
• Molecular Weight: 219.24
• Mol File: 160695-26-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 83.5-84 °C(Solv: hexane (110-54-3); toluene (108-88-3))
• Boiling Point: 393.1 °C at 760 mmHg
• Flash Point: 191.6 °C
• Appearance: /
• Density: 1.223 g/cm³
• Vapor Pressure: 2.18E-06mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -3.13±0.40(Predicted)
• CAS DataBase Reference: (R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE(160695-26-1)
• EPA Substance Registry System: (R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE(160695-26-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 160695-26-1(Hazardous Substances Data)

Usage

Description

(R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE is a chiral chemical compound that belongs to the oxazolidinone class, which is known for its synthetic antibiotic properties. (R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE features a phenyl group and a propionyl group attached to an oxazolidinone ring, with the "R" denoting its specific stereochemistry, indicating the presence of two possible isomeric forms that are mirror images of each other. Oxazolidinones are recognized for their antimicrobial capabilities and are widely utilized in the medical field to combat various infections, especially those that are resistant to conventional antibiotics. The effectiveness and applications of (R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE are contingent upon the details of its formulation and the specific context in which it is employed.

Uses

Used in Medical Applications:
(R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE is used as an antimicrobial agent for treating a variety of infections, particularly those that are resistant to other antibiotics. Its application in this context is due to the compound's inherent antimicrobial properties, which make it a valuable tool in the medical field for combating antibiotic-resistant infections.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE is used as a potential candidate for the development of new drugs. Its unique structure and antimicrobial activity make it a promising starting point for the creation of novel therapeutics that could address the growing challenge of antibiotic resistance.
Used in Research and Development:
(R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE is also utilized in research settings to study its chemical properties, potential interactions with biological systems, and its effectiveness against specific types of infections. This research can lead to a better understanding of the compound's capabilities and limitations, as well as inform the development of new formulations or applications.

InChI:InChI=1/C12H13NO3/c1-2-11(14)13-10(8-16-12(13)15)9-6-4-3-5-7-9/h3-7,10H,2,8H2,1H3/t10-/m0/s1

Upstream product

• 201300-96-1 (4'R)-2-bromo-1-(2'-oxo-4'-phenyloxazolidin-3'-yl)propan-1-one 
• 100-52-7 benzaldehyde 
• 56613-80-0 D-2-phenylglycinol 
• 90319-52-1 (4R)-phenyl-2-oxazolidinone 
• 802294-64-0 propionic acid 
• 79-03-8 propionyl chloride 
• 86217-38-1 4-phenyl-2-oxazolidinone 
• 123-62-6 propionic acid anhydride 
• 186581-53-3 diazomethane 
• 124-38-9 carbon dioxide 
• 120666-53-7 (R)-benzyl [2-hydroxy-1-phenylethyl]carbamate 

Downstream Products

• 1335544-75-6 (4R)-4-phenyl-3-[(2R)-3,3,3-trifluoro-2-methylpropanoyl]-1,3-oxazolidin-2-one 
• 1314641-25-2 (R)-3-((S)-2-methylpent-4-enoyl)-4-phenyloxazolidin-2-one 
• 1258861-66-3 (4R)-3-[(2R,3S)-3-hydroxy-2-methylpent-4-enoyl]-4-phenyl-oxazolidin-2-one 
• 1258861-81-2 (4R)-3-[(2R,3S)-3-triethylsilyloxy-2-methylpent-4-enoyl]-4-phenyl-oxazolidin-2-one 
• 1199613-15-4 (4R)-3-[(2R,3S,4E)-3-hydroxy-2-methyl-6-(4-methoxybenzyloxy)hex-4-enoyl]-4-phenyloxazolidin-2-one 
• 1199613-26-7 (4R)-3-[(2R,3S,4E)-6-tert-butyldimethylsilyloxy-3-hydroxy-2-methylhex-4-enoyl]-4-phenyloxazolidin-2-one 
• 1199613-22-3 (4R)-3-{(2R,3S,6S,7R,4E)-6-benzyloxy-7-[(4R,5S,6S)-6-((3S,5S)-3-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)octyn-1-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl]-3-hydroxy-2-methyloct-4-enoyl}-4-phenyloxazolidin-2-one 
• 1236299-78-7 C₂₈H₄₃NO₆Si 
• 615579-62-9 ethyl (3S)-3-[(4R)-2-oxo-4-phenyl-1,3-oxazolan-3-yl]pentanoate 

Relevant articles and documents

Diastereoselective Electrochemical Carboxylation of Chiral α-Bromocarboxylic Acid Derivatives: An Easy Access to Unsymmetrical Alkylmalonic Ester Derivatives

The diastereoselective electrochemical carboxylation of chiral N-(2-bromoacyl)oxazolidin-2-ones has been studied. This reaction was carried out by cathodic reduction of the C - Br bond, in the presence of carbon dioxide, followed by treatment with diazomethane. The yields and the diastereomeric ratio of the two epimeric alkylmalonic acid derivatives are strongly affected by various factors: solvent-supporting electrolyte system, temperature, electrode material, electrolysis conditions, oxazolidinone moiety. The higher yields (88%) were obtained starting from N-(2-bromopropionyl)-4R-phenyloxazolidin-2-one la, but with poor diastereoselectivity (61:39). The two epimers were easily separated by flash chromatography. The best results were achieved using a different chiral auxiliary: Oppolzer's camphor sultam. Starting from 1j a good yield in carboxylated product was obtained (80%) with excellent diastereoselectivity (98:2). These chiral alkylmalonic acid derivatives are valuable building blocks in the synthesis of molecules with biological activity and of chiral propane-1,3-diols derivatives.

Diastereoselective Electrophilic Trifluoromethylthiolation of Chiral Oxazolidinones: Access to Enantiopure α-SCF3 Alcohols

Lithium imide enolates featuring Evans’ chiral oxazolidinone auxiliary were involved in diastereoselective α-trifluoromethylthiolation with electrophilic SCF3 donors. Diastereopure products were isolated and converted to enantiopure α-SCF3 alcohols without racemisation. (Figure presented.).

PROCESS FOR THE PREPARATION OF (1S,3S,7S,10R,11S,12S,16R)-7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-[(1E)-1-METHYL-2-(2-METHYL-4-THIAZOLYL)ETHENYL]-17-OXA-4-AZABICYCLO[14.1.0]HEPTADECANE-5,9-DIONE AND INTERMEDIATES THEREOF

The present invention relates to an improved process for the preparation of (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2- methyl-4-thiazolyl)ethenyl]- 17-oxa-4-azabicyclo[ 14.1.0]heptadecane-5,9-dione represented by the following structural formula I and intermediates thereof. The present invention also provides novel intermediate compounds useful for the preparation of compound of formula I and its intermediates.