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CAS No.: | 485-64-3 |
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Name: | (8alpha,9R)-10,11-dihydrocinchonan-9-ol |
Article Data: | 19 |
Molecular Structure: | |
Formula: | C19H24 N2 O |
Molecular Weight: | 296.412 |
Synonyms: | Hydrocinchonidine(6CI,7CI,8CI); (-)-Dihydrocinchonidine; (-)-Hydrocinchonidine;10,11-Dihydrocinchonidine; Cinchamidine; Dihydrocinchonidine |
Density: | 1.18g/cm3 |
Melting Point: | 230° |
Boiling Point: | 467.1°Cat760mmHg |
Flash Point: | 236.3°C |
PSA: | 36.36000 |
LogP: | 3.32650 |
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 10h; | 92% |
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 12h; | 86% |
With triethylsilane; 1% Pd on activated carbon In water at 45℃; for 24h; Reagent/catalyst; Green chemistry; chemoselective reaction; | 83% |
1-[(3R,4S)-3-Ethyl-4-(3-quinolin-4-yl-oxiranylmethyl)-piperidin-1-yl]-2,2,2-trifluoro-ethanone
A
dihydrocinchonine
B
(-)-hydrocinchonidine
Conditions | Yield |
---|---|
With potassium carbonate 1.) MeOH, rt, 2 h, 2.) toluene, EtOH, reflux 24 h; Yield given. Multistep reaction. Yields of byproduct given; |
(-)-hydrocinchonidine
Conditions | Yield |
---|---|
With sodium ethanolate; aluminium | |
With sodium ethanolate; zinc | |
With sodium ethanolate; aluminium | |
With sodium ethanolate; zinc |
Conditions | Yield |
---|---|
With ethanol; palladium Hydrogenation; |
pentan-1-ol
dihydrocinchonine
A
hydrocinchonine
B
(-)-hydrocinchonidine
C
hydrocinchonidine
Conditions | Yield |
---|---|
With potassium hydroxide; pentan-1-ol |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: lithium diisopropylamide, pyridine hydrochloride 2: 90 percent / pyridine hydrochloride / methanol; pyridine; various solvent(s) / 36 h / Ambient temperature 3: 1) water 2.) NH4OAc, NaCNBH3 / 1) β-glucosidase / 2.) pH=6.2, 18 h 4: 1.) 3percent HCl, 2.) NaCNBH3 / 1.) aq MeOH, reflux, 40 min 5: 2.) CF3CO3H, Na2HPO4 / 1.) 0 grad C, 2.) CH2Cl2, rt, 12 h 6: 1.) K2CO3 / 1.) MeOH, rt, 2 h, 2.) toluene, EtOH, reflux 24 h View Scheme |
[4]quinolyl-acetic acid
(-)-hydrocinchonidine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 90 percent / pyridine hydrochloride / methanol; pyridine; various solvent(s) / 36 h / Ambient temperature 2: 1) water 2.) NH4OAc, NaCNBH3 / 1) β-glucosidase / 2.) pH=6.2, 18 h 3: 1.) 3percent HCl, 2.) NaCNBH3 / 1.) aq MeOH, reflux, 40 min 4: 2.) CF3CO3H, Na2HPO4 / 1.) 0 grad C, 2.) CH2Cl2, rt, 12 h 5: 1.) K2CO3 / 1.) MeOH, rt, 2 h, 2.) toluene, EtOH, reflux 24 h View Scheme |
4-[(E)-3-((3R,4R)-3-Ethyl-piperidin-4-yl)-propenyl]-quinoline
(-)-hydrocinchonidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 2.) CF3CO3H, Na2HPO4 / 1.) 0 grad C, 2.) CH2Cl2, rt, 12 h 2: 1.) K2CO3 / 1.) MeOH, rt, 2 h, 2.) toluene, EtOH, reflux 24 h View Scheme |