(4R)-4-benzyl-3-[(1S,2S)-2-hydroxycyclopent-3-ene-1-carbonyl]-1,3-oxazolidin-2-one

• ChemBase ID: 170399
• Molecular Formular: C16H17NO4
• Molecular Mass: 287.31048
• Monoisotopic Mass: 287.11575803
• SMILES: C1OC(=O)N([C@@H]1Cc1ccccc1)C(=O)[C@H]1CC=C[C@@H]1O
• Canonical SMILES: O[C@H]1C=CC[C@@H]1C(=O)N1C(=O)OC[C@H]1Cc1ccccc1
• InChI: InChI=1S/C16H17NO4/c18-14-8-4-7-13(14)15(19)17-12(10-21-16(17)20)9-11-5-2-1-3-6-11/h1-6,8,12-14,18H,7,9-10H2/t12-,13+,14+/m1/s1
• InChIKey: DDSIGQSDXSMOPL-RDBSUJKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-benzyl-3-[(1S,2S)-2-hydroxycyclopent-3-ene-1-carbonyl]-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4R)-4-benzyl-3-[(1S,2S)-2-hydroxycyclopent-3-ene-1-carbonyl]-1,3-oxazolidin-2-one
• Synonyms: (4R)-3-[((1S,2S)-2-Hydroxy-3-cyclopenten-1-yl)carbonyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one; (4R)-3-[[(1S,2S)-2-Hydroxy-3-cyclopenten-1-yl]carbonyl]-4-(phenylmethyl)-2-oxazolidinone

Database IDs

• CAS Number: 324741-99-3
• PubChem SID: 164226309
• PubChem CID: 67112360

CALCULATED PROPERTIES

• Acid pKa: 14.356276
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.9347719
• LogD (pH = 7.4): 1.9347719
• Log P: 1.9347719
• Molar Refractivity: 76.7002 cm^3
• Polarizability: 29.660612 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Oil

DETAILS

Toronto Research Chemicals - H926250

Used in the synthesis of enantioselective synthesis of carbocyclic ribavirin, its analogs and other antiviral agents.

REFERENCES

• Kuang, R. et al.; Tetrahedron Lett. 41, 9575 (2000)