(6R)-6-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-5-(4-fluorophenyl)-3,6-dihydro-2H-oxazine

• ChemBase ID: 162612
• Molecular Formular: C20H16F7NO2
• Molecular Mass: 435.3353624
• Monoisotopic Mass: 435.1069263
• SMILES: N1=C([C@@H](O[C@@H](c2cc(cc(c2)C(F)(F)F)C(F)(F)F)C)OCC1)c1ccc(cc1)F
• Canonical SMILES: Fc1ccc(cc1)C1=NCCO[C@@H]1O[C@@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C
• InChI: InChI=1S/C20H16F7NO2/c1-11(13-8-14(19(22,23)24)10-15(9-13)20(25,26)27)30-18-17(28-6-7-29-18)12-2-4-16(21)5-3-12/h2-5,8-11,18H,6-7H2,1H3/t11-,18-/m1/s1
• InChIKey: KHOSCFXAHZBOCH-ADLMAVQZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R)-6-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-5-(4-fluorophenyl)-3,6-dihydro-2H-oxazine
• IUPAC Traditional name: (2R)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-oxazine
• Synonyms: (2R)-2-[(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-5,6-dihydro-2H-1,4-oxazine

Database IDs

• CAS Number: 380499-07-0
• PubChem SID: 162256747
• PubChem CID: 10274609

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 5.8142414
• LogD (pH = 7.4): 5.8154035
• Log P: 5.8154182
• Molar Refractivity: 95.0438 cm^3
• Polarizability: 34.548286 Å^3
• Polar Surface Area: 30.82 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - B657140

Intermediate in the preparation of enantiomerically pure Aprepitant diastereomers and derivatives.

REFERENCES

• Huskey, S., et al.: Drug Metab. Disposition, 32, 246 (2004)