(1S,9R,10R)-4-methoxy-17-methyl-3-phenoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-13-one

• ChemBase ID: 176498
• Molecular Formular: C24H27NO3
• Molecular Mass: 377.47608
• Monoisotopic Mass: 377.19909373
• SMILES: c1(c(c2c(cc1)C[C@@H]1[C@H]3[C@@]2(CC(=O)CC3)CCN1C)Oc1ccccc1)OC
• Canonical SMILES: COc1ccc2c(c1Oc1ccccc1)[C@@]13CCN([C@H](C2)[C@@H]3CCC(=O)C1)C
• InChI: InChI=1S/C24H27NO3/c1-25-13-12-24-15-17(26)9-10-19(24)20(25)14-16-8-11-21(27-2)23(22(16)24)28-18-6-4-3-5-7-18/h3-8,11,19-20H,9-10,12-15H2,1-2H3/t19-,20+,24-/m0/s1
• InChIKey: GUMLCSIEVNHVBR-ROKPMTFOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9R,10R)-4-methoxy-17-methyl-3-phenoxy-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-13-one
• IUPAC Traditional name: (1S,9R,10R)-4-methoxy-17-methyl-3-phenoxy-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-13-one
• Synonyms: 3-Methoxy-17-methyl-4-phenoxy-morphinan-6-one; 3-Methoxy-N-methyl-6-oxo-4-phenoxy-morphinan; 4-Phenoxy-6-oxo-levomethorphan

Database IDs

• CAS Number: 4978-42-1
• PubChem SID: 164232408
• PubChem CID: 16720550

CALCULATED PROPERTIES

• Acid pKa: 19.332033
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.91011196
• LogD (pH = 7.4): 2.6547544
• Log P: 3.814844
• Molar Refractivity: 109.4454 cm^3
• Polarizability: 42.7676 Å^3
• Polar Surface Area: 38.77 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Brown-Orange Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - P318620

Morphinan derivative. Intermediate in the preparation of Levomethorphan (L375850) and indolo/thiazolo-morphinans as opioid receptor binder.

REFERENCES

• Zhang, A. et al.; J. Med. Chem.; 50, 2747 (2007)