(3R,4S)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-1-phenylazetidin-2-one

• ChemBase ID: 166272
• Molecular Formular: C24H22FNO3
• Molecular Mass: 391.4347832
• Monoisotopic Mass: 391.15837179
• SMILES: [C@@H]1(C(=O)N([C@@H]1c1ccc(cc1)O)c1ccccc1)CC[C@@H](c1ccc(cc1)F)O
• Canonical SMILES: Oc1ccc(cc1)[C@@H]1[C@@H](CC[C@@H](c2ccc(cc2)F)O)C(=O)N1c1ccccc1
• InChI: InChI=1S/C24H22FNO3/c25-18-10-6-16(7-11-18)22(28)15-14-21-23(17-8-12-20(27)13-9-17)26(24(21)29)19-4-2-1-3-5-19/h1-13,21-23,27-28H,14-15H2/t21-,22+,23-/m1/s1
• InChIKey: YWZUFJFIXFJKBD-XPWALMASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-1-phenylazetidin-2-one
• IUPAC Traditional name: (3R,4S)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-1-phenylazetidin-2-one
• Synonyms: (3R,4S)-3-[(3S)-3-(4-Fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-1-phenyl-2-azetidinone; Desfluoro Ezetimibe

Database IDs

• CAS Number: 302781-98-2
• PubChem SID: 162260405
• PubChem CID: 58827445

CALCULATED PROPERTIES

• Acid pKa: 9.484299
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.4163814
• LogD (pH = 7.4): 4.4128847
• Log P: 4.416426
• Molar Refractivity: 108.6453 cm^3
• Polarizability: 41.898754 Å^3
• Polar Surface Area: 60.77 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D289945

An impurity of the cholesterol absorption inhibitor Ezetimibe (E975000).

REFERENCES

• Anon.: IP.com J., 7, 4 (2007)