1-[(S)-[4-(benzyloxy)phenyl](hydroxy)methyl]-N-(4-fluorophenyl)-4-oxocyclohexane-1-carboxamide

• ChemBase ID: 169193
• Molecular Formular: C27H26FNO4
• Molecular Mass: 447.4980432
• Monoisotopic Mass: 447.18458654
• SMILES: [C@H](C1(CCC(=O)CC1)C(=O)Nc1ccc(cc1)F)(O)c1ccc(cc1)OCc1ccccc1
• Canonical SMILES: O=C1CCC(CC1)(C(=O)Nc1ccc(cc1)F)[C@H](c1ccc(cc1)OCc1ccccc1)O
• InChI: InChI=1S/C27H26FNO4/c28-21-8-10-22(11-9-21)29-26(32)27(16-14-23(30)15-17-27)25(31)20-6-12-24(13-7-20)33-18-19-4-2-1-3-5-19/h1-13,25,31H,14-18H2,(H,29,32)/t25-/m0/s1
• InChIKey: BEDDNSKYSRIEEJ-VWLOTQADSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(S)-[4-(benzyloxy)phenyl](hydroxy)methyl]-N-(4-fluorophenyl)-4-oxocyclohexane-1-carboxamide
• IUPAC Traditional name: 1-[(S)-[4-(benzyloxy)phenyl](hydroxy)methyl]-N-(4-fluorophenyl)-4-oxocyclohexane-1-carboxamide
• Synonyms: (S)-N-(4-Fluorophenyl)-1-[hydroxy[4-(phenylmethoxy)phenyl]methyl]-4-oxo-cyclohexanecarboxamide

Database IDs

• CAS Number: 182227-24-3
• PubChem SID: 162263325
• PubChem CID: 10789584

CALCULATED PROPERTIES

• Acid pKa: 13.5819025
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.914228
• LogD (pH = 7.4): 4.9142275
• Log P: 4.914228
• Molar Refractivity: 124.6153 cm^3
• Polarizability: 47.57284 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Tetrahydrofuran

DETAILS

Toronto Research Chemicals - F595410

Intermediate in the synthesis of a cholesterol absorption inhibitor.

REFERENCES

• Wu, G. & Tormos, W.; J. Org. Chem. 62, 6412 (1997)