(3S,4R)-3-[(2H-1,3-benzodioxol-5-yloxy)(2H2)methyl]-1-benzyl-4-(4-fluorophenyl)(6,6-2H2)piperidine

• ChemBase ID: 161900
• Molecular Formular: C26H26FNO3
• Molecular Mass: 419.4879432
• Monoisotopic Mass: 419.18967192
• SMILES: C1CN(C[C@H]([C@@H]1c1ccc(cc1)F)COc1ccc2c(c1)OCO2)Cc1ccccc1
• Canonical SMILES: Fc1ccc(cc1)[C@@H]1CCN(C[C@H]1COc1ccc2c(c1)OCO2)Cc1ccccc1
• InChI: InChI=1S/C26H26FNO3/c27-22-8-6-20(7-9-22)24-12-13-28(15-19-4-2-1-3-5-19)16-21(24)17-29-23-10-11-25-26(14-23)31-18-30-25/h1-11,14,21,24H,12-13,15-18H2/t21-,24-/m0/s1
• InChIKey: AGTKMLMRHVWXHN-URXFXBBRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R)-3-[(2H-1,3-benzodioxol-5-yloxy)(^2H₂)methyl]-1-benzyl-4-(4-fluorophenyl)(6,6-^2H₂)piperidine
• IUPAC Traditional name: (3S,4R)-3-[(2H-1,3-benzodioxol-5-yloxy)(^2H₂)methyl]-1-benzyl-4-(4-fluorophenyl)(6,6-^2H₂)piperidine
• Synonyms: (3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-(phenylmethyl)-piperidine-d4; (-)-N-Benzylparoxetine-d4; trans N-Benzyl Paroxetine-d4

Database IDs

• PubChem SID: 162256035
• PubChem CID: 46780780

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.0188177
• LogD (pH = 7.4): 3.5755236
• Log P: 5.2557697
• Molar Refractivity: 117.931 cm^3
• Polarizability: 45.9141 Å^3
• Polar Surface Area: 30.93 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - B288587

Labelled Paroxetine intermediate.

REFERENCES

• Oefner, C., et al.: Chem. Biol., 6, 127 (1999)
• Bower, J., et al.: Org. Biomol. Chem., 4, 1868 (2006)