(4S)-4-benzyl-3-propanoyl-1,3-oxazolidin-2-one

• ChemBase ID: 77308
• Molecular Formular: C13H15NO3
• Molecular Mass: 233.2631
• Monoisotopic Mass: 233.10519335
• SMILES: N1(C(=O)CC)[C@@H](Cc2ccccc2)COC1=O
• Canonical SMILES: CCC(=O)N1C(=O)OC[C@@H]1Cc1ccccc1
• InChI: InChI=1S/C13H15NO3/c1-2-12(15)14-11(9-17-13(14)16)8-10-6-4-3-5-7-10/h3-7,11H,2,8-9H2,1H3/t11-/m0/s1
• InChIKey: WHOBYFHKONUTMW-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-benzyl-3-propanoyl-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4S)-4-benzyl-3-propanoyl-1,3-oxazolidin-2-one
• Synonyms: (R)-4-Benzyl-3-propionyloxazolidin-2-one; (S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone; (S)-4-Benzyl-3-propionyloxazolidin-2-one; (4S)-3-(1-Oxopropyl)-4-(phenylmethyl)-2-oxazolidinone; (+)-4-Benzyl-3-propionyl-2-oxazolidinone; (4S)-4-Benzyl-3-propanoyloxazolidin-2-one; (4S)-4-Benzyl-3-propionyl-1,3-oxazolidin-2-one; (S)-N-Propionyl-4-benzyl-1,3-oxazolidin-2-one; 3-[1-Oxopropyl]-4(S)-(phenylmethyl)-2-oxazolidinone; (S)-4-Benzyl-3-propionyl-2-oxazolidinone; (4s)-(+)-4-benzyl-3-propionyl-2-oxazolidinone; (S)-(+)-4-苄基-3-丙酰基-2-噁唑烷酮

Database IDs

• CAS Number: 101711-78-8
• MDL Number: MFCD00269687; MFCD00269688
• PubChem SID: 162042181; 24869502
• PubChem CID: 2733696

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.4031994
• LogD (pH = 7.4): 2.4031994
• Log P: 2.4031994
• Molar Refractivity: 62.2478 cm^3
• Polarizability: 24.473927 Å^3
• Polar Surface Area: 46.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Colourless Solid
• Melting Point: 44-46 °C(lit.)
• Optical Rotation: [α]20/D +97°, c = 1 in ethanol

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3

Product Information

• Purity: 95+%; 98%; 99%
• Optical Purity: ee: 99% (HPLC)
• Empirical Formula (Hill Notation): C13H15NO3

DETAILS

Sigma Aldrich - 458775

Application
Versatile chiral auxiliary for asymmetric synthesis.1
Packaging
5 g in glass bottle

Toronto Research Chemicals - B288650

Intermediate in the preparation of Albaconazole.

REFERENCES

• Gupta, S., et al.: ChemBioChem, 9, 1609 (2007)
• Tran, J., et al.: J. Med. Chem., 50, 6356 (2007)