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

• ChemBase ID: 150195
• Molecular Formular: C15H13NO2
• Molecular Mass: 239.26922
• Monoisotopic Mass: 239.09462866
• SMILES: c1ccc(cc1)[C@H]1[C@H](OC(=O)N1)c1ccccc1
• Canonical SMILES: O=C1N[C@H]([C@H](O1)c1ccccc1)c1ccccc1
• InChI: InChI=1S/C15H13NO2/c17-15-16-13(11-7-3-1-4-8-11)14(18-15)12-9-5-2-6-10-12/h1-10,13-14H,(H,16,17)/t13-,14+/m0/s1
• InChIKey: LTENIVFVXMCOQI-UONOGXRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5R)-4,5-diphenyl-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4S,5R)-4,5-diphenyl-1,3-oxazolidin-2-one
• Synonyms: (4S,5R)-(-)-cis-4,5-Diphenyl-2-oxazolidinone; (4S,5R)-(-)-顺-4,5-二苯基-2-噁唑烷酮

Database IDs

• CAS Number: 23204-70-8
• MDL Number: MFCD00799526
• PubChem SID: 162244356; 24868340
• PubChem CID: 9859564

CALCULATED PROPERTIES

• Acid pKa: 12.485818
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 3.2096343
• LogD (pH = 7.4): 3.2096312
• Log P: 3.2096343
• Molar Refractivity: 67.5828 cm^3
• Polarizability: 26.611261 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 227-232 °C(lit.)
• Optical Rotation: [α]23/D -57±4°, c = 2 in chloroform (or methanol)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C15H13NO2

DETAILS

Sigma Aldrich - 447447

Application
Versatile chiral auxiliary used in a variety of highly diastereoselective reactions such as Michael additions,1 Diels-Alder reactions,2 cyclopropanations,3 and allylations.4
Packaging
1 g in glass bottle