572-59-8

Basic information

• Product Name: (9R)-6'-methoxycinchonan-9-ol
• Synonyms: (9R)-6'-methoxycinchonan-9-ol;Epiquindine;(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 NO: 572-59-8
• Molecular Formula: C20H24N2O2
• Molecular Weight: 324.41676
• EINECS: 209-340-6
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 572-59-8.mol
• Article Data: 37

Chemical Properties

• Melting Point: 111-113°
• Boiling Point: 462.75°C (rough estimate)
• Flash Point: 253.7°C
• Appearance: /
• Density: 1.1294 (rough estimate)
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: 2-8°C
• PKA: 12.80±0.20(Predicted)
• CAS DataBase Reference: (9R)-6'-methoxycinchonan-9-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (9R)-6'-methoxycinchonan-9-ol(572-59-8)
• EPA Substance Registry System: (9R)-6'-methoxycinchonan-9-ol(572-59-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-42/43
• Safety Statements: 22-36/37-45
• Hazardous Substances Data: 572-59-8(Hazardous Substances Data)

Usage

Description

(9R)-6'-methoxycinchonan-9-ol is an alkaloid found in the mixture of amorphous bases left after the extraction of the four primary alkaloids of Cinchona bark. It is stereoisomeric with epiQuinine and crystallizes in colorless leaflets from Et20, exhibiting fluorescence in dilute H2SO4. (9R)-6'-methoxycinchonan-9-ol is dextrorotatory with specific optical rotation values and forms various derivatives upon chemical reactions.

Uses

Used in Antimalarial Applications:
(9R)-6'-methoxycinchonan-9-ol is used as an antimalarial agent for its effectiveness against malaria-causing parasites. As the 9-epimer of Quinidine (Q685000), it plays a crucial role in the treatment and prevention of malaria, a disease that poses significant health challenges worldwide.
Used in Pharmaceutical Industry:
(9R)-6'-methoxycinchonan-9-ol is used as an active pharmaceutical ingredient for the development of new drugs targeting various diseases. Its unique chemical properties and stereoisomeric nature make it a valuable compound for research and drug discovery, potentially leading to the creation of novel therapeutics.
Used in Chemical Research:
(9R)-6'-methoxycinchonan-9-ol is used as a research tool in the field of organic chemistry, particularly for studying the properties and reactions of stereoisomers and alkaloids. Its various derivatives and the ability to undergo different chemical transformations make it an essential compound for understanding the structure-activity relationships in drug development and other chemical applications.

References

Thron, Dirscherl., Annalen, 521,48 (1935)

Upstream product

• 865853-19-6 (3R,4S)-4-[(2S,3S)-3-(6-Methoxy-quinolin-4-yl)-oxiranylmethyl]-3-vinyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 865853-23-2 2-(trimethylsilyl)ethyl (3R,4S)-4-(2-oxoethyl)-3-vinylpiperidine-1-carboxylate 
• 865853-17-4 (3R,4R)-4-[(E)-3-(6-Methoxy-quinolin-4-yl)-allyl]-3-vinyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 865853-22-1 (3R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-vinyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 946491-91-4 (3R,4S)-4-[(2S,3S)-2,3-Dihydroxy-3-(6-methoxy-quinolin-4-yl)-propyl]-3-vinyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 865853-21-0 (3R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 865853-20-9 (3R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-[2-(2,2-dimethyl-propionyloxy)-ethyl]-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 92288-15-8 (6-methoxyquinolin-4-yl)methanol 
• 35189-37-8 (+)-N-benzoylmeroquinene aldehyde 
• 5437-98-9 4'-methoxyacetoacetanilide 
• 53899-32-4 (6-Methoxy-quinolin-4-ylmethyl)-phosphonic acid diethyl ester 
• 41037-26-7 6-methoxy-4-methylquinoline 
• 233746-07-1 4-chloromethyl-6-methoxyquinoline 
• 85598-65-8 [(3R,4S)-4-(2-Hydroxy-ethyl)-3-vinyl-piperidin-1-yl]-phenyl-methanone 

Downstream Products

• 14528-53-1 6'-methoxycinchoninone 
• 108646-60-2 (9R)-9-hydroxy-6'-methoxy-1-methyl-cinchonanium; iodide 
• 78034-56-7 (S)-(6-Methoxy-quinolin-4-yl)-((1S,2S,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol; compound with [benzyl-(2-oxo-2H-quinolin-1-yl)-amino]-acetic acid 
• 1435-55-8 hydroquinidine 
• 56-54-2 quinine 
• 135754-90-4 C₂₇H₄₂NO₂⁽¹⁺⁾*C₂₁H₁₂Br₄O₅S^(2-)*C₂₀H₂₄N₂O₂*H⁽¹⁺⁾ 
• 60-93-5 quinine hydrochloride 
• 83434-80-4 (R)-(6-Methoxy-quinolin-4-yl)-((2R,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol; compound with (2S,3R)-3-methyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid 
• 83434-80-4 N-Ts-D-syn-3-MePro-quinine 
• 120186-13-2 quinidine-diphenylphosphinite 
• 84-31-1 (6-Methoxy-quinolin-4-yl)-((1S,2S,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanone 
• 135754-88-0 C₂₇H₄₂NO₂⁽¹⁺⁾*C₂₀H₂₄N₂O₂*C₁₉H₈Br₄O₅S^(2-)*H⁽¹⁺⁾ 
• 84-31-1 6'-methoxycinchonidone 
• 84-55-9 viquidil 

Relevant articles and documents

Nickel-Catalyzed Dehydrogenation of N-Heterocycles Using Molecular Oxygen

Herein, an efficient and selective nickel-catalyzed dehydrogenation of five- and six-membered N-heterocycles is presented. The transformation occurs in the presence of alkyl, alkoxy, chloro, free hydroxyl and primary amine, internal and terminal olefin, trifluoromethyl, and ester functional groups. Synthesis of an important ligand and the antimalarial drug quinine is demonstrated. Mechanistic studies revealed that the cyclic imine serves as the key intermediate for this stepwise transformation.

Anti-Selective Asymmetric Nitro-Michael Reaction of Furanones: Diastereocontrol by Catalyst

Catalyst-controlled switching of diastereoselectivity from high syn-selectivity (>98/2 dr, syn) to anti-selectivity (up to 96/4 dr, anti) of the asymmetric nitro-Michael reaction of furanones is described. Anti-diastereoselectivity of the nitro-Michael reaction is very rare. With 0.1-5 mol % loadings of an epi-quinine catalyst, the reaction of 5-substituted 2(3H)-furanones with nitroalkenes smoothly proceeded to give the anti-Michael adducts in good yields (up to 95%) with excellent diastereo- and enantioselectivities (up to 96/4 dr, anti; up to 99% ee). DFT calculations support a model that accounts the high anti-diastereoselectivity. (Chemical Equation Presented).

An easy route to exotic 9-epimers of 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations through two inversions of configuration

Four exotic chiral organocatalysts, 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations, were conveniently synthesized for the first time in 27-72% total yields through two conversions of configuration at the 9-stereogenic centers of commercially available cinchona alkaloids.