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(9R)-6'-methoxycinchonan-9-ol

(9R)-6'-methoxycinchonan-9-ol Basic information
Product Name:(9R)-6'-methoxycinchonan-9-ol
Synonyms:Epiquindine;(9R)-6'-methoxycinchonan-9-ol;(8R,9R)-6'-Methoxycinchonan-9-ol;9-Epiquinidine;Epiquinidine;(R)-(6-methoxy-4-quinolyl)-[(2R,4S,5R)-5-vinylquinuclidin-2-yl]methanol;(R)-[(4S,5R,7R)-5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl]-(6-methoxyquinolin-4-yl)methanol;(9R)-
CAS:572-59-8
MF:C20H24N2O2
MW:324.42
EINECS:209-340-6
Product Categories:Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:572-59-8.mol
(9R)-6'-methoxycinchonan-9-ol Structure
(9R)-6'-methoxycinchonan-9-ol Chemical Properties
Melting point 111-113°
alpha D25 +107.8° (c = 1.02 in ethanol)
Boiling point 462.75°C (rough estimate)
density 1.1294 (rough estimate)
refractive index 1.5700 (estimate)
storage temp. 2-8°C
pka12.80±0.20(Predicted)
Safety Information
Hazard Codes Xn
Risk Statements 22-42/43
Safety Statements 22-36/37-45
MSDS Information
(9R)-6'-methoxycinchonan-9-ol Usage And Synthesis
DescriptionThis alkaloid is stereoisomeric with epiQuinine and occurs in 'Quinoidine', the mixture of amorphous bases left after extraction of the four primary alkaloids of Cinchona bark. It crystallizes in colourless leaflets from Et20 and is fluorescent in dilute H2S04, It is dextrorotatory with [α]19D + 102.4° (c 0.8648, EtOH) and furnishes a dihydrochloride, m.p. 195-6°C (dec.); [α]20D + 45.5° (c 0.8012, EtOH); a hydrobromide, m.p. 240°C; thiocyanate, m.p. 193°C; [α]20D + 44.5° (H20) and the dibenzoyl-(+)-tartrate, m.p. 167°C; [α]201D + 3.7° (c 0.8068, EtOH-CHCI 3 ). Catalytic hydrogenation with Pd gives the dihydro derivative, m.p. 122°C; [α]22D + 73.1° (c 0.766, EtOH).
UsesThe 9-epimer of Quinidine (Q685000). Antimalarial.
ReferencesThron, Dirscherl., Annalen, 521,48 (1935)
(9R)-6'-methoxycinchonan-9-ol Preparation Products And Raw materials
Quinine
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