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

• ChemBase ID: 173086
• Molecular Formular: C22H29NO3
• Molecular Mass: 355.47056
• Monoisotopic Mass: 355.21474379
• SMILES: c1(cc2c(cc1)C[C@@H]1[C@]3([C@@]2(CC(=O)CC3)CCN1CC1CCC1)O)OC
• Canonical SMILES: COc1ccc2c(c1)[C@@]13CCN([C@H](C2)[C@]3(O)CCC(=O)C1)CC1CCC1
• InChI: InChI=1S/C22H29NO3/c1-26-18-6-5-16-11-20-22(25)8-7-17(24)13-21(22,19(16)12-18)9-10-23(20)14-15-3-2-4-15/h5-6,12,15,20,25H,2-4,7-11,13-14H2,1H3/t20-,21-,22-/m1/s1
• InChIKey: XPWGUPWFWBKZLG-YPAWHYETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R,10S)-17-(cyclobutylmethyl)-10-hydroxy-4-methoxy-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-13-one
• IUPAC Traditional name: (1R,9R,10S)-17-(cyclobutylmethyl)-10-hydroxy-4-methoxy-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-13-one
• Synonyms: 17-(Cyclobutylmethyl)-14-hydroxy-3-methoxy-morphinan-6-one; (-)-3-Methoxy-6-oxo Butorphanol

Database IDs

• CAS Number: 67753-29-1
• PubChem SID: 164228996
• PubChem CID: 57257006

CALCULATED PROPERTIES

• Acid pKa: 13.683788
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.75565374
• LogD (pH = 7.4): 0.5728685
• Log P: 2.614264
• Molar Refractivity: 101.0447 cm^3
• Polarizability: 39.689594 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol

DETAILS

Toronto Research Chemicals - M265260

Intermediate in the preparation of opioid receptor agonists and antagonists.