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

General Description

"(R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE" is a chemical compound that belongs to oxazolidinones, a class of synthetic antibiotics. Its specific structure comprises a phenyl group and a propionyl group attached to an oxazolidinone ring. (R) indicative of its chiral nature, suggesting that the molecule can exist in two different isomeric forms that are mirror images of each other. Oxazolidinones, such as this compound, are often recognized for their antimicrobial properties and are commonly used in the medical field to treat a range of infections, particularly those resistant to other antibiotics. The specific activity and applications of (R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE, however, can greatly depend on the characteristics of its precise formulation and the context of its use.

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

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

Downstream Products

• 439278-07-6 (R)-4-phenyl-3-((2R,3S)-3-hydroxy-2-methylnonanoyl)-1,3-oxazolidin-2-one 
• 439278-12-3 (R)-4-phenyl-3-((2R,3S)-3-hydroxy-2-methyloctanoyl)-1,3-oxazolidin-2-one 
• 615579-48-1 (4R)-4-phenyl-3-(1S)-1-[(trimethylsilyl)oxy]propyl-1,3-oxazolan-2-one 
• 900807-41-2 (R)-3-[(2R,3S)-3-Hydroxy-2-methyl-5-((4S,6S)-2,2,6-trimethyl-[1,3]dioxan-4-yl)-pentanoyl]-4-phenyl-oxazolidin-2-one 
• 615579-75-4 (3S)-3-[(4R)-2-oxo-4-phenyl-1,3-oxazolan-3-yl]pentanoic acid 
• 615579-62-9 ethyl (3S)-3-[(4R)-2-oxo-4-phenyl-1,3-oxazolan-3-yl]pentanoate 
• 1236299-78-7 C₂₈H₄₃NO₆Si 
• 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 
• 1199613-26-7 (4R)-3-[(2R,3S,4E)-6-tert-butyldimethylsilyloxy-3-hydroxy-2-methylhex-4-enoyl]-4-phenyloxazolidin-2-one 
• 1199613-15-4 (4R)-3-[(2R,3S,4E)-3-hydroxy-2-methyl-6-(4-methoxybenzyloxy)hex-4-enoyl]-4-phenyloxazolidin-2-one 
• 1258861-81-2 (4R)-3-[(2R,3S)-3-triethylsilyloxy-2-methylpent-4-enoyl]-4-phenyl-oxazolidin-2-one 
• 1258861-66-3 (4R)-3-[(2R,3S)-3-hydroxy-2-methylpent-4-enoyl]-4-phenyl-oxazolidin-2-one 

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.