(1'R,9'R,10'S)-4'-methoxy-17'-methyl-3'-phenoxy-17'-azaspiro[1,3-dioxolane-2,13'-tetracyclo[7.5.3.01,10.02,7]heptadecane]-2'(7'),3',5'-trien-10'-ol

• ChemBase ID: 170749
• Molecular Formular: C26H31NO5
• Molecular Mass: 437.52804
• Monoisotopic Mass: 437.2202231
• SMILES: c1(c(c2c(cc1)C[C@@H]1[C@]3([C@@]2(CC2(CC3)OCCO2)CCN1C)O)Oc1ccccc1)OC
• Canonical SMILES: COc1ccc2c(c1Oc1ccccc1)[C@@]13CCN([C@H](C2)[C@]3(O)CCC2(C1)OCCO2)C
• InChI: InChI=1S/C26H31NO5/c1-27-13-12-24-17-25(30-14-15-31-25)10-11-26(24,28)21(27)16-18-8-9-20(29-2)23(22(18)24)32-19-6-4-3-5-7-19/h3-9,21,28H,10-17H2,1-2H3/t21-,24-,26-/m1/s1
• InChIKey: OXNBTXGUEQFEQC-YMVVMYQSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'R,9'R,10'S)-4'-methoxy-17'-methyl-3'-phenoxy-17'-azaspiro[1,3-dioxolane-2,13'-tetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadecane]-2'(7'),3',5'-trien-10'-ol
• IUPAC Traditional name: (1'R,9'R,10'S)-4'-methoxy-17'-methyl-3'-phenoxy-17'-azaspiro[1,3-dioxolane-2,13'-tetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadecane]-2'(7'),3',5'-trien-10'-ol
• Synonyms: 14-Hydroxy-3-methoxy-17-methyl-4-phenoxy-morphinan-6-one Cyclic Ethylene Acetal; 14-Hydroxy-3-methoxy-17-methyl-6-oxo-4-phenoxy-morphinan 6-Ethylene Ketal

Database IDs

• CAS Number: 21020-34-8
• PubChem SID: 164226659
• PubChem CID: 71749121

CALCULATED PROPERTIES

• Polar Surface Area: 60.39 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 13.638425
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.11904625
• LogD (pH = 7.4): 1.8221935
• Log P: 3.1495454
• Molar Refractivity: 120.9921 cm^3
• Polarizability: 47.573204 Å^3

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Off-White Foam

DETAILS

Toronto Research Chemicals - H946310

(-)-Butorphanol intermediate.

REFERENCES

• Li, F., et al.: Chem. Biol. Drug Des., 74, 335 (2009)