(5R,6R)-6-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-5-(4-fluorophenyl)morpholin-3-one

• ChemBase ID: 162616
• Molecular Formular: C20H16F7NO3
• Molecular Mass: 451.3347624
• Monoisotopic Mass: 451.10184092
• SMILES: N1[C@@H]([C@@H](O[C@@H](c2cc(cc(c2)C(F)(F)F)C(F)(F)F)C)OCC1=O)c1ccc(cc1)F
• Canonical SMILES: O=C1CO[C@@H]([C@H](N1)c1ccc(cc1)F)O[C@@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C
• InChI: InChI=1S/C20H16F7NO3/c1-10(12-6-13(19(22,23)24)8-14(7-12)20(25,26)27)31-18-17(28-16(29)9-30-18)11-2-4-15(21)5-3-11/h2-8,10,17-18H,9H2,1H3,(H,28,29)/t10-,17-,18-/m1/s1
• InChIKey: UISOBKKSNVFVOF-AQQIJUCISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R,6R)-6-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-5-(4-fluorophenyl)morpholin-3-one
• IUPAC Traditional name: (5R,6R)-6-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-5-(4-fluorophenyl)morpholin-3-one
• Synonyms: (5R,6R)-6-[(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-5-(4-fluorophenyl)-3-morpholinone

Database IDs

• CAS Number: 419574-33-7
• PubChem SID: 162256751
• PubChem CID: 20722769

CALCULATED PROPERTIES

• Acid pKa: 7.687772
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.947843
• LogD (pH = 7.4): 4.794584
• Log P: 4.950331
• Molar Refractivity: 95.1061 cm^3
• Polarizability: 35.167572 Å^3
• Polar Surface Area: 47.56 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B657160

A diastereomeric byproduct formed during the synthesis of Aprepitant metabolites.

REFERENCES

• Huskey, S., et al.: Drug Metab. Disposition, 31, 785 (2003)