2-carbamoyl-10-oxo-2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-9-yl acetate

• ChemBase ID: 159048
• Molecular Formular: C17H14N2O4
• Molecular Mass: 310.30406
• Monoisotopic Mass: 310.09535694
• SMILES: c12c(cccc1)N(c1c(cccc1)C(=O)C2OC(=O)C)C(=O)N
• Canonical SMILES: CC(=O)OC1c2ccccc2N(c2c(C1=O)cccc2)C(=O)N
• InChI: InChI=1S/C17H14N2O4/c1-10(20)23-16-12-7-3-5-9-14(12)19(17(18)22)13-8-4-2-6-11(13)15(16)21/h2-9,16H,1H3,(H2,18,22)
• InChIKey: ZKWJEEHQNGPADU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-carbamoyl-10-oxo-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-9-yl acetate
• IUPAC Traditional name: 2-carbamoyl-10-oxo-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-9-yl acetate
• Synonyms: (+/-)-10-(Acetyloxy)-10,11-dihydro-11-oxo-5H-dibenz[b,f]azepine-5-carboxamide; 5-Carbamoyl-10-11-dihydro-11-oxo-5H-dibenz[b,f]azepine-10-yl Acetate; 10-Acetyloxy Oxcarbazepine

Database IDs

• CAS Number: 113952-21-9
• PubChem SID: 162253183
• PubChem CID: 13901528

CALCULATED PROPERTIES

• Acid pKa: 9.8221245
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.5441229
• LogD (pH = 7.4): 1.5425049
• Log P: 1.5441437
• Molar Refractivity: 82.0476 cm^3
• Polarizability: 31.549442 Å^3
• Polar Surface Area: 89.7 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; DMSO; Methanol
• Apperance: Yellow-Orange Solid

DETAILS

Toronto Research Chemicals - A167650

An intermediate in the preparation of Carbamazepine metabolites.

REFERENCES

• Heckendorn, R., et al.: Helv. Chimica Acta, 70, 1955 (1987)