(S)-{5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(quinolin-4-yl)methanol

• ChemBase ID: 295452
• Molecular Formular: C19H22N2O
• Molecular Mass: 294.39078
• Monoisotopic Mass: 294.17321333
• SMILES: C=CC1CN2CCC1CC2[C@H](c1ccnc2c1cccc2)O
• Canonical SMILES: C=CC1CN2CCC1CC2[C@H](c1ccnc2c1cccc2)O
• InChI: InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13?,14?,18?,19-/m0/s1
• InChIKey: KMPWYEUPVWOPIM-QHQSXHFQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (S)-{5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(quinolin-4-yl)methanol
• IUPAC Traditional name: cinchonine
• Synonyms: (+)-Cinchonine; (+)-辛可宁

Database IDs

• CAS Number: 118-10-5
• EC Number: 204-234-6
• MDL Number: MFCD00064372
• Beilstein Number: 89689
• Merck Index: 142287
• PubChem SID: 180680983
• PubChem CID: 8350

CALCULATED PROPERTIES

• Acid pKa: 13.8773155
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.60487753
• LogD (pH = 7.4): 0.92435837
• Log P: 2.6711352
• Molar Refractivity: 88.2304 cm^3
• Polarizability: 35.8717 Å^3
• Polar Surface Area: 36.36 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 253-258°C
• Optical Rotation: +225 (c=0.5 in ethanol)

Safety Information

• Storage Warning: Light Sensitive
• RTECS: GD3500000
• European Hazard Symbols: X
• Risk Statements: 22
• Safety Statements: 36
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Hazard statements: H301
• GHS Precautionary statements: P264-P270-P301+P310-P321-P405-P501A

Product Information

• Purity: 98+%, cont. up to 3% quinidine/dihydroquinidine and 3% quinine/dihydroquinine

REFERENCES

• Resolving agent for chiral acids. For practical details for use in the resolution of 1,1'-bi(2-naphthol) via the cyclic phosphate ester, see: Org. Synth. Coll., 8, 50 (1993).