572-60-1

Basic information

• Product Name: (8alpha,9S)-6'-methoxycinchonan-9-ol
• Synonyms: (8alpha,9S)-6'-methoxycinchonan-9-ol;(8S,9S)-6'-Methoxycinchonan-9-ol;(8α,9S)-6'-Methoxycinchonan-9-ol;9-Epiquinine;9-epi-Quinine;(3-ethenyl-6-methoxy-1-azabicyclo[2.2.2]octan-7-yl)-quinolin-4-ylmethanol;(3-ethenyl-6-methoxy-1-azabicyclo[2.2.2]octan-7-yl)-quinolin-4-yl-methanol;(7-methoxy-5-vinyl-quinuclidin-2-yl)-(4-quinolyl)methanol
• CAS NO: 572-60-1
• Molecular Formula: C20H24N2O2
• Molecular Weight: 324.41676
• EINECS: 209-341-1
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 572-60-1.mol
• Article Data: 37

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 495.88 °C at 760 mmHg
• Flash Point: 253.699 °C
• Appearance: /
• Density: 1.218 g/cm³
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethanol (Slightly), Methanol (Very Slightly)
• PKA: 12.80±0.20(Predicted)
• CAS DataBase Reference: (8alpha,9S)-6'-methoxycinchonan-9-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (8alpha,9S)-6'-methoxycinchonan-9-ol(572-60-1)
• EPA Substance Registry System: (8alpha,9S)-6'-methoxycinchonan-9-ol(572-60-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-42/43
• Safety Statements: 22-36/37-45
• Hazardous Substances Data: 572-60-1(Hazardous Substances Data)

Usage

Uses

The 9-epimer of Quinine (Q694000). Antimalarial.

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.