(2R)-2-hydroxy-N-{8-methyl-9-oxo-8-azatricyclo[9.4.0.02,7]pentadeca-1(11),2(7),3,5,12,14-hexaen-10-yl}-2-phenylacetamide

• ChemBase ID: 167665
• Molecular Formular: C23H20N2O3
• Molecular Mass: 372.4165
• Monoisotopic Mass: 372.14739251
• SMILES: c12C(C(=O)N(c3c(c1cccc2)cccc3)C)NC(=O)[C@@H](c1ccccc1)O
• Canonical SMILES: O=C([C@@H](c1ccccc1)O)NC1c2ccccc2c2c(N(C1=O)C)cccc2
• InChI: InChI=1S/C23H20N2O3/c1-25-19-14-8-7-12-17(19)16-11-5-6-13-18(16)20(23(25)28)24-22(27)21(26)15-9-3-2-4-10-15/h2-14,20-21,26H,1H3,(H,24,27)/t20?,21-/m1/s1
• InChIKey: CXWBCMJIHSHUEV-BPGUCPLFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-hydroxy-N-{8-methyl-9-oxo-8-azatricyclo[9.4.0.0^2,^7]pentadeca-1(11),2(7),3,5,12,14-hexaen-10-yl}-2-phenylacetamide
• IUPAC Traditional name: (2R)-2-hydroxy-N-{8-methyl-9-oxo-8-azatricyclo[9.4.0.0^2,^7]pentadeca-1(11),2(7),3,5,12,14-hexaen-10-yl}-2-phenylacetamide
• Synonyms: N-(6,7-Dihydro-5-methyl-6-oxo-5H-dibenz[b,d]azepin-7-yl)-(αR)-hydroxy-benzeneacetamide

Database IDs

• PubChem SID: 162261798
• PubChem CID: 71316180

CALCULATED PROPERTIES

• Acid pKa: 11.889006
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.6993291
• LogD (pH = 7.4): 2.6993165
• Log P: 2.6993294
• Molar Refractivity: 106.3366 cm^3
• Polarizability: 42.377926 Å^3
• Polar Surface Area: 69.64 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D449295

An intermediate in the production of γ-secretase inhibitors

REFERENCES

• Fauq, A., et al.: Bioorg. Med. Chem. Lett., 17, 6392 (2007)