(1S,9R,10S)-17-(cyclobutylmethyl)-4-methoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-10-ol

• ChemBase ID: 172909
• Molecular Formular: C22H31NO2
• Molecular Mass: 341.48704
• Monoisotopic Mass: 341.23547924
• SMILES: c1(cc2c(cc1)C[C@@H]1[C@]3([C@@]2(CCCC3)CCN1CC1CCC1)O)OC
• Canonical SMILES: COc1ccc2c(c1)[C@]13CCCC[C@]3([C@@H](C2)N(CC1)CC1CCC1)O
• InChI: InChI=1S/C22H31NO2/c1-25-18-8-7-17-13-20-22(24)10-3-2-9-21(22,19(17)14-18)11-12-23(20)15-16-5-4-6-16/h7-8,14,16,20,24H,2-6,9-13,15H2,1H3/t20-,21+,22-/m1/s1
• InChIKey: DTVODKGBEXBXFW-BHIFYINESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9R,10S)-17-(cyclobutylmethyl)-4-methoxy-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-10-ol
• IUPAC Traditional name: (1S,9R,10S)-17-(cyclobutylmethyl)-4-methoxy-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-10-ol
• Synonyms: (-)-N-Cyclobutylmethyl-14β-hydroxy-3-methoxymorphinan; 17-(Cyclobutylmethyl)-3-methoxy-morphinan-14-ol; (-)-3-Methoxy Butorphanol

Database IDs

• CAS Number: 63730-48-3
• PubChem SID: 164228819
• PubChem CID: 13080261

CALCULATED PROPERTIES

• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 13.705968
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.31066245
• LogD (pH = 7.4): 0.94211805
• Log P: 3.7934818
• Molar Refractivity: 100.4033 cm^3
• Polarizability: 39.546364 Å^3

DETAILS

Toronto Research Chemicals - M261255

Protected intermediate of Butorphanol.

REFERENCES

• Craviso, G., et al.: Mol. Pharmacol., 23, 629 (1983)