benzyl 4-hydroxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-17-carboxylate

• ChemBase ID: 161765
• Molecular Formular: C24H27NO3
• Molecular Mass: 377.47608
• Monoisotopic Mass: 377.19909373
• SMILES: c1(cc2c(cc1)CC1C3C2(CCCC3)CCN1C(=O)OCc1ccccc1)O
• Canonical SMILES: Oc1ccc2c(c1)C13CCCCC3C(C2)N(CC1)C(=O)OCc1ccccc1
• InChI: InChI=1S/C24H27NO3/c26-19-10-9-18-14-22-20-8-4-5-11-24(20,21(18)15-19)12-13-25(22)23(27)28-16-17-6-2-1-3-7-17/h1-3,6-7,9-10,15,20,22,26H,4-5,8,11-14,16H2
• InChIKey: GPYJBNLHEROROX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl 4-hydroxy-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-triene-17-carboxylate
• IUPAC Traditional name: benzyl 4-hydroxy-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-triene-17-carboxylate
• Synonyms: 3-Hydroxy-(9α13α,14α)-morphinan-17-carboxylic Acid Phenylmethyl Ester; N-Benzyloxycarbonyl N-Desmethyl Dextrorphan

Database IDs

• CAS Number: 159723-96-3
• PubChem SID: 162255900
• PubChem CID: 22070211

CALCULATED PROPERTIES

• Acid pKa: 9.410959
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.918486
• LogD (pH = 7.4): 4.9143496
• Log P: 4.918539
• Molar Refractivity: 108.5883 cm^3
• Polarizability: 42.331455 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Pale Orange to Brown Solid
• Melting Point: 64-66°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B286180

An intermediate in the preparation of labelled Dextrorphan derivatives and metabolites

REFERENCES

• Kim, H., et al.: Life Sci., 72, 1883 (2003)
• Kim, J., et al.: Chem. Pharm. Bull., 56, 985 (2003)