(4R,5S)-4-methyl-5-phenyl-1,3-oxazolidin-2-one

• ChemBase ID: 144802
• Molecular Formular: C10H11NO2
• Molecular Mass: 177.19984
• Monoisotopic Mass: 177.0789786
• SMILES: C[C@@H]1[C@@H](OC(=O)N1)c1ccccc1
• Canonical SMILES: C[C@H]1NC(=O)O[C@H]1c1ccccc1
• InChI: InChI=1S/C10H11NO2/c1-7-9(13-10(12)11-7)8-5-3-2-4-6-8/h2-7,9H,1H3,(H,11,12)/t7-,9-/m1/s1
• InChIKey: PPIBJOQGAJBQDF-VXNVDRBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S)-4-methyl-5-phenyl-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4R,5S)-4-methyl-5-phenyl-1,3-oxazolidin-2-one
• Synonyms: (4R,5S)-4-Methyl-5-phenyl-2-oxazolidinone; (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone; (4R,5S)-4-Methyl-5-phenyl-2-oxazolidinone; (4r,5s)-(+)-4-methyl-5-phenyl-2-oxazolidinone; (4R,5S)-4-甲基-5-苯基-2-噁唑啉酮; (4R,5S)-(+)-4-甲基-5-苯基-2-噁唑啉酮; (4R,5S)-4-甲基-5-苯基-2-噁唑啉酮

Database IDs

• CAS Number: 77943-39-6
• MDL Number: MFCD00010845
• Beilstein Number: 1211705
• PubChem SID: 24858003; 24885704; 162239014
• PubChem CID: 2733812

CALCULATED PROPERTIES

• Acid pKa: 12.913281
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.8419691
• LogD (pH = 7.4): 1.8419679
• Log P: 1.8419691
• Molar Refractivity: 47.7188 cm^3
• Polarizability: 18.862381 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 118-121 °C; 121-123 °C(lit.)
• Optical Rotation: [α]18/D +168°, c = 2 in chloroform; [α]20/D +160±3°, c = 1% in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (sum of enantiomers, GC); 97%; 98%; 99%
• Grade: purum
• Optical Purity: ee: 98% (GLC)
• Empirical Formula (Hill Notation): C10H11NO2
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 298891

Packaging
5, 25 g in glass bottle
Application
Chiral auxiliary in condensation reactions with acyl halides1,2,3 and carboxylic acids.4,5,6

Sigma Aldrich - 68700

Other Notes
The 3-acyl derivatives are used in many enantioselective reactions: aldol, alkylation and acylation reactions1,2,3; the 3-acrylate derivatives in DA cycloadditions4