(4R)-4-benzyl-1,3-oxazolidin-2-one

• ChemBase ID: 69958
• Molecular Formular: C10H11NO2
• Molecular Mass: 177.19984
• Monoisotopic Mass: 177.0789786
• SMILES: O1C(=O)N[C@@H](C1)Cc1ccccc1
• Canonical SMILES: O=C1OC[C@H](N1)Cc1ccccc1
• InChI: InChI=1S/C10H11NO2/c12-10-11-9(7-13-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,11,12)/t9-/m1/s1
• InChIKey: OJOFMLDBXPDXLQ-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-benzyl-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4R)-4-benzyl-1,3-oxazolidin-2-one
• Synonyms: (R)-4-Benzyl-2-oxazolidinone; (R)-(+)-4-Benzyl-2-oxazolidinone; (4R)-4-(Phenylmethyl)-2-oxazolidinone; (+)-4-Benzyl-2-oxazolidinone; (4R)-4-(Phenylmethyl)-1,3-oxazolidin-2-one; (4R)-4-Benzyl-1,3-oxazolidin-2-one; (4R)-Benzyloxazolidin-2-one; (R)-4-Benzyl-2-oxazolidinone; (4S)-4-Benzyl-2-oxo-1,3-oxazolidine; (4S)-4-Benzyl-1,3-oxazolidin-2-one; (4R)-4-Benzyl-2-oxo-1,3-oxazolidine; (4R)-4-Benzyl-1,3-oxazolidin-2-one; (R)-4-苄基-2-噁唑烷酮; (R)-(+)-4-苯甲基-2-噁唑烷酮

Database IDs

• CAS Number: 102029-44-7; 90719-32-7
• MDL Number: MFCD00064496; MFCD00010846
• Beilstein Number: 4782551
• PubChem SID: 162035683; 24858151; 24848261
• PubChem CID: 2734969

CALCULATED PROPERTIES

• Acid pKa: 13.030782
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.7140553
• LogD (pH = 7.4): 1.7140545
• Log P: 1.7140553
• Molar Refractivity: 48.055 cm^3
• Polarizability: 18.866823 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid
• Melting Point: 86-88 °C; 86-89°C; 86-90°C; 87-88°C; 88-90 °C
• Optical Rotation: [α]18/D +64°, c = 1 in chloroform; [α]20/D +63±2°, c = 1% in chloroform; +64 (c=1 in chloroform)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Hygroscopic; IRRITANT; Irritant
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.5% (sum of enantiomers, GC); 95+%; 98%; 99%
• Grade: puriss.
• Empirical Formula (Hill Notation): C10H11NO2

DETAILS

Sigma Aldrich - 300977

Application
Used in the synthesis of HIV protease inhibitors.1
Versatile chiral auxiliary for asymmetric synthesis. For a recent review, see Aldrichimica Acta.
Packaging
1, 5, 25 g in glass bottle

Sigma Aldrich - 13615

Other Notes
The N-acyl derivatives are used in many enantioselective reactions: aldol reactions with carbonyl compounds. It gives higher yields than other auxiliaries;1 alkylation and Michael reaction;2,3 DA-cycloadditions of 3-acrylates.4

Toronto Research Chemicals - B285820

An oxazolidinone used in chiral auxiliary asymetric synthesis.