(S)-[(2R,4R,5S)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol

• ChemBase ID: 295162
• Molecular Formular: C20H24N2O2
• Molecular Mass: 324.41676
• Monoisotopic Mass: 324.18377802
• SMILES: COc1ccc2c(c1)c(ccn2)[C@@H]([C@H]1C[C@H]2CCN1C[C@H]2C=C)O
• Canonical SMILES: C=C[C@@H]1CN2CC[C@@H]1C[C@@H]2[C@H](c1ccnc2c1cc(OC)cc2)O
• InChI: InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m1/s1
• InChIKey: LOUPRKONTZGTKE-FQZPYLGXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (S)-[(2R,4R,5S)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
• IUPAC Traditional name: (S)-[(2R,4R,5S)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
• Synonyms: Quinine, anhydrous; 无水奎宁

Database IDs

• CAS Number: 130-95-0
• EC Number: 205-003-2
• MDL Number: MFCD00198096
• Beilstein Number: 91867
• Merck Index: 148061
• PubChem SID: 180680693
• PubChem CID: 637552

CALCULATED PROPERTIES

• Acid pKa: 13.892048
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.7213722
• LogD (pH = 7.4): 0.863951
• Log P: 2.513464
• Molar Refractivity: 94.6936 cm^3
• Polarizability: 38.350784 Å^3
• Polar Surface Area: 45.59 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ca 177°C dec.
• Optical Rotation: -166 (c=1 in ethanol)

Safety Information

• Storage Warning: Light Sensitive
• RTECS: VA6020000
• European Hazard Symbols: X
• Risk Statements: 22-36/37/38-42/43
• Safety Statements: 22-24-26-37-45
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS08
• GHS Hazard statements: H301-H315-H319-H317-H335-H334
• GHS Precautionary statements: P285-P301+P310-P305+P351+P338-P302+P352-P405-P501A

Product Information

• Purity: 99% (total base), may cont. up to 5% dihydroquinine

REFERENCES

• Resolving agent for chiral acids. For a review of resolutions, see: Topics Stereochem., 6, 107 (1977).