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

• ChemBase ID: 171257
• Molecular Formular: C20H24N2O3
• Molecular Mass: 340.41616
• Monoisotopic Mass: 340.17869264
• SMILES: c1(ccc2c(c1)c(ccn2)[C@@H]([C@@H]1N2CC[C@@H](C1)[C@@](C2)(C=C)O)O)OC
• 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-XVVDYKMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,6R)-3-ethenyl-6-[(S)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol
• IUPAC Traditional name: (1S,3R,4S,6R)-3-ethenyl-6-[(S)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol
• Synonyms: (3α,9S)- 6'-Methoxy-cinchonan-3,9-diol; 3-epi-Hydroxyquinidine; ICQ 7; (3R)-Hydroxyquinidine

Database IDs

• CAS Number: 60761-51-5
• PubChem SID: 164227167
• PubChem CID: 13217487

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: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Off-White Solid
• Melting Point: 92-100°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H953240

Isomer of (3S)-Hydroxyquinidine.

REFERENCES

• Carrol, F.I., et al.: J. CHem. Soc. Perkin Trans. 1, 12, 3017 (1991).