(1'R,9'R,10'S)-4'-methoxy-17'-methyl-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: 170760
• Molecular Formular: C20H27NO4
• Molecular Mass: 345.43268
• Monoisotopic Mass: 345.19400835
• SMILES: c1(cc2c(cc1)C[C@@H]1[C@]3([C@@]2(CC2(CC3)OCCO2)CCN1C)O)OC
• Canonical SMILES: COc1ccc2c(c1)[C@@]13CCN([C@H](C2)[C@]3(O)CCC2(C1)OCCO2)C
• InChI: InChI=1S/C20H27NO4/c1-21-8-7-18-13-19(24-9-10-25-19)5-6-20(18,22)17(21)11-14-3-4-15(23-2)12-16(14)18/h3-4,12,17,22H,5-11,13H2,1-2H3/t17-,18-,20-/m1/s1
• InChIKey: SSKUWIKLIAYCJP-QWFCFKBJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'R,9'R,10'S)-4'-methoxy-17'-methyl-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-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: 6,6-(Ethylenedioxy)-14-hydroxy-3-methoxy-N-methyl-morphinan; 14-Hydroxy-3-methoxy-17-methyl-morphinan-6-one Cyclic 1,2-Ethanediyl Acetal; 14-Hydroxy-3-methoxy-17-methyl-6-oxo-morphinan 6-Ethylene Ketal

Database IDs

• CAS Number: 21020-35-9
• PubChem SID: 164226670
• PubChem CID: 71749124

CALCULATED PROPERTIES

• Acid pKa: 13.686795
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.5660974
• LogD (pH = 7.4): 0.013402621
• Log P: 1.6492584
• Molar Refractivity: 94.7513 cm^3
• Polarizability: 37.249104 Å^3
• Polar Surface Area: 51.16 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - H946360

(-)-Butorphanol intermediate.

REFERENCES

• Li, F., et al.: Bioorg. Med. Chem. Lett., 19, 4603 (2009)