(4S)-4-benzyl-3-[(2R)-2-[(2R)-2-(2,4-difluorophenyl)oxiran-2-yl](3,3,3-2H3)propanoyl]-1,3-oxazolidin-2-one

• ChemBase ID: 167438
• Molecular Formular: C21H19F2NO4
• Molecular Mass: 387.3766664
• Monoisotopic Mass: 387.12821453
• SMILES: c1c(ccc(c1F)[C@@]1([C@H](C(=O)N2[C@H](COC2=O)Cc2ccccc2)C)OC1)F
• Canonical SMILES: Fc1ccc(c(c1)F)[C@@]1(CO1)[C@H](C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1)C
• InChI: InChI=1S/C21H19F2NO4/c1-13(21(12-28-21)17-8-7-15(22)10-18(17)23)19(25)24-16(11-27-20(24)26)9-14-5-3-2-4-6-14/h2-8,10,13,16H,9,11-12H2,1H3/t13-,16-,21+/m0/s1
• InChIKey: SJRVUCOOQMMMJY-UYTHQXMGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-benzyl-3-[(2R)-2-[(2R)-2-(2,4-difluorophenyl)oxiran-2-yl](3,3,3-^2H₃)propanoyl]-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4S)-4-benzyl-3-[(2R)-2-[(2R)-2-(2,4-difluorophenyl)oxiran-2-yl](3,3,3-^2H₃)propanoyl]-1,3-oxazolidin-2-one
• Synonyms: (4S)-3-[(2R)-2-[(2R)-2-(2,4-Difluorophenyl)-2-oxiranyl]-1-oxopropyl]-4-(phenylmethyl)-2-oxazolidinone-d3; (4S)-3-[(2R)-2-[(2R)-2-(2,4-Difluorophenyl)oxiranyl]-1-oxopropyl]-4-benzyl-2-oxazolidinone-d3

Database IDs

• PubChem SID: 162261571
• PubChem CID: 71316075

CALCULATED PROPERTIES

• Acid pKa: 17.486046
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.130429
• LogD (pH = 7.4): 4.130429
• Log P: 4.130429
• Molar Refractivity: 95.9844 cm^3
• Polarizability: 37.129963 Å^3
• Polar Surface Area: 59.14 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Hexanes; Methanol

DETAILS

Toronto Research Chemicals - D445917

Intermediate in the preparation of labelled Albaconazole.

REFERENCES

• Bartroli, J., et al.: J. Med. Chem., 41, 1869 (1998)
• Uchida, T., et al.: Bioorg. Med. Chem. Lett., 18, 6538 (1998)