3-[(3R,4R)-3-ethenylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-one

• ChemBase ID: 177300
• Molecular Formular: C20H24N2O2
• Molecular Mass: 324.41676
• Monoisotopic Mass: 324.18377802
• SMILES: c1c(cc2c(c1)nccc2C(=O)CC[C@H]1[C@H](CNCC1)C=C)OC
• Canonical SMILES: C=C[C@H]1CNCC[C@H]1CCC(=O)c1ccnc2c1cc(OC)cc2
• InChI: InChI=1S/C20H24N2O2/c1-3-14-13-21-10-8-15(14)4-7-20(23)17-9-11-22-19-6-5-16(24-2)12-18(17)19/h3,5-6,9,11-12,14-15,21H,1,4,7-8,10,13H2,2H3/t14-,15+/m0/s1
• InChIKey: DKRSEIPLAZTSFD-LSDHHAIUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(3R,4R)-3-ethenylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-one
• IUPAC Traditional name: 3-[(3R,4R)-3-ethenylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-one
• Synonyms: 3-[(3R,4R)-3-Ethenyl-4-piperidinyl]-1-(6-methoxy-4-quinolinyl)-1-propanone Hydrochloride; (3R-cis)-3-(3-Ethenyl-4-piperidinyl)-1-(6-methoxy-4-quinolinyl)-1-propanone Hydrochloride; Quinicine Hydrochloride; (3R,4R)-4-[3-Oxo-3-(6-methoxyquinolin-4-yl)propyl]-3-vinylpiperidine Hydrochloride; Chinicine Hydrochloride; Chinotoxin; Permiran; Viquidil Hydrochloride; Quinotoxine Hydrochloride

Database IDs

• CAS Number: 52211-63-9
• PubChem SID: 164233210
• PubChem CID: 65753

CALCULATED PROPERTIES

• Acid pKa: 16.558184
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.45737347
• LogD (pH = 7.4): 0.03953673
• Log P: 2.7731783
• Molar Refractivity: 95.5697 cm^3
• Polarizability: 38.52976 Å^3
• Polar Surface Area: 51.22 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - Q753500

An isomer of quinine; occurs naturally as the d-form. Present in small quantities in cinchona barks. Vasodilator (cerebral).

REFERENCES

• Grethe, et al.: Helv. Chim. Acta, 56, 1485 (1973)