(3R,4S,6S)-3-ethenyl-6-[(R)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol

• ChemBase ID: 171258
• Molecular Formular: C20H24N2O3
• Molecular Mass: 340.41616
• Monoisotopic Mass: 340.17869264
• SMILES: c12c(ccc(c1)OC)nccc2[C@H]([C@@H]1C[C@H]2[C@](CN1CC2)(O)C=C)O
• Canonical SMILES: C=C[C@]1(O)CN2CC[C@H]1C[C@H]2[C@@H](c1ccnc2c1cc(OC)cc2)O
• InChI: InChI=1S/C20H24N2O3/c1-3-20(24)12-22-9-7-13(20)10-18(22)19(23)15-6-8-21-17-5-4-14(25-2)11-16(15)17/h3-6,8,11,13,18-19,23-24H,1,7,9-10,12H2,2H3/t13-,18-,19+,20-/m0/s1
• InChIKey: BSRUJCFCZKMFMB-JZOCTASASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,6S)-3-ethenyl-6-[(R)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol
• IUPAC Traditional name: (1S,3R,4S,6S)-3-ethenyl-6-[(R)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol
• Synonyms: (3α,8α,9R)- 6'-methoxycinchonan-3,9-diol; (3R)-Hydroxyquinine; (3R)-3-Hydroxy Quinine

Database IDs

• CAS Number: 128241-59-8
• PubChem SID: 164227168
• PubChem CID: 13217485

CALCULATED PROPERTIES

• Acid pKa: 13.55172
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.3222476
• LogD (pH = 7.4): 0.4145601
• Log P: 1.6659791
• Molar Refractivity: 95.9137 cm^3
• Polarizability: 38.94357 Å^3
• Polar Surface Area: 65.82 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 114-116°C

DETAILS

Toronto Research Chemicals - H953245

Isomer of (3R)-3-Hydroxy Quinine