14528-51-9

Basic information

• Product Name: (8alpha)-6'-methoxycinchonan
• Synonyms: (8alpha)-6'-methoxycinchonan;EINECS 238-547-4;(8α)-6'-Methoxycinchonan;Deoxyquinine
• CAS NO: 14528-51-9
• Molecular Formula: C₂₀H₂₄N₂O
• Molecular Weight: 308.41736
• EINECS: 238-547-4
• Mol File: 14528-51-9.mol

Chemical Properties

• Boiling Point: 450.8°Cat760mmHg
• Flash Point: 226.4°C
• Appearance: /
• Density: 1.14g/cm³
• CAS DataBase Reference: (8alpha)-6'-methoxycinchonan(CAS DataBase Reference)
• NIST Chemistry Reference: (8alpha)-6'-methoxycinchonan(14528-51-9)
• EPA Substance Registry System: (8alpha)-6'-methoxycinchonan(14528-51-9)

Safety Data

• Hazardous Substances Data: 14528-51-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(8alpha)-6'-methoxycinchonan is used as an antimalarial agent for its ability to inhibit the growth of the malaria parasite, providing a natural treatment for fevers and malaria.
Used in Traditional Medicine:
(8alpha)-6'-methoxycinchonan is used as a traditional medicine ingredient for its long-standing use in treating fevers and malaria, highlighting its historical significance in healthcare.
Used in Research and Development:
(8alpha)-6'-methoxycinchonan is used as a research compound for studying its potential anti-inflammatory and analgesic effects, contributing to the development of new medications for various conditions.
Used in Synthesis of Bioactive Compounds:
(8alpha)-6'-methoxycinchonan is used as a building block in the synthesis of other bioactive compounds, indicating its utility in creating new pharmaceuticals and therapeutic agents.

Upstream product

• 594-61-6 2-methyllactic acid 
• 130-95-0 Quinine 
• 339046-93-4 (4S,5R)-5-Azidomethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(6-methoxy-quinolin-4-yl)-hept-6-en-2-one 
• 339046-95-6 4-{(2S,4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-piperidin-2-ylmethyl}-6-methoxy-quinoline 
• 339046-94-5 4-{(4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-3,4,5,6-tetrahydro-pyridin-2-ylmethyl}-6-methoxy-quinoline 
• 339046-91-2 (3S,4R)-4-Azidomethyl-3-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-hex-5-enal 
• 339046-89-8 (E)-(2R,3R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methoxy-2-vinyl-pent-4-en-1-ol 
• 339046-96-7 2-[(2S,4R,5R)-2-(6-Methoxy-quinolin-4-ylmethyl)-5-vinyl-piperidin-4-yl]-ethanol 
• 339046-88-7 (3R,4R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-vinyl-dihydro-furan-2-one 
• 339046-86-5 3-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid diethylamide 
• 339046-99-0 (S)-3-Hydroxymethyl-pent-4-enoic acid diethylamide 
• 107080-45-5 (S)-(+)-β-vinyl-γ-butyrolactone 
• 41037-26-7 6-methoxy-4-methylquinoline 
• 339046-87-6 3-(tert-butyl-dimethyl-silanyloxymethyl)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-pent-4-enoic acid diethylamide 

Downstream Products

• 130-95-0 quinine 

Relevant articles and documents

Nickel-catalyzed reductive deoxygenation of diverse C-O bond-bearing functional groups

We report a catalytic method for the direct deoxygenation of various C-O bond-containing functional groups. Using a Ni(II) pre-catalyst and silane reducing agent, alcohols, epoxides, and ethers are reduced to the corresponding alkane. Unsaturated species including aldehydes and ketones are also deoxygenated via initial formation of an intermediate silylated alcohol. The reaction is chemoselective for C(sp3)-O bonds, leaving amines, anilines, aryl ethers, alkenes, and nitrogen-containing heterocycles untouched. Applications toward catalytic deuteration, benzyl ether deprotection, and the valorization of biomass-derived feedstocks demonstrate some of the practical aspects of this methodology.

New Mechanism for Cinchona Alkaloid-Catalysis Allows for an Efficient Thiophosphorylation Reaction

An efficient synthesis of nucleoside 5′-monothiophosphates under mild reaction conditions using commercially available thiophosphoryl chloride was achieved with a cinchona alkaloid catalyst. A detailed mechanistic study of the reaction was undertaken, employing a combination of reaction kinetics, NMR spectroscopy, and computational modeling, to better understand the observed reactivity. Taken collectively, the results support an unprecedented mechanism for this class of organocatalyst.

The hydroxyl functionality and a rigid proximal N are required for forming a novel non-covalent quinine-heme complex

Quinoline antimalarial drugs bind both monomeric and dimeric forms of free heme, with distinct preferences depending on the chemical environment. Under biological conditions, chloroquine (CQ) appears to prefer to bind to μ-oxo dimeric heme, while quinine (QN) preferentially binds monomer. To further explore this important distinction, we study three newly synthesized and several commercially available QN analogues lacking various functional groups. We find that removal of the QN hydroxyl lowers heme affinity, hemozoin (Hz) inhibition efficiency, and antiplasmodial activity. Elimination of the rigid quinuclidyl ring has similar effects, but elimination of either the vinyl or methoxy group does not. Replacing the quinuclidyl N with a less rigid tertiary aliphatic N only partially restores activity. To further study these trends, we probe drug-heme interactions via NMR studies with both Fe and Zn protoporphyrin IX (FPIX, ZnPIX) for QN, dehydroxyQN (DHQN), dequinuclidylQN (DQQN), and deamino-dequinuclidylQN (DADQQN). Magnetic susceptibility measurements in the presence of FPIX demonstrate that these compounds differentially perturb FPIX monomer-dimer equilibrium. We also isolate the QN-FPIX complex formed under mild aqueous conditions and analyze it by mass spectrometry, as well as fluorescence, vibrational, and solid-state NMR spectroscopies. The data elucidate key features of QN pharmacology and allow us to propose a refined model for the preferred binding of QN to monomeric FPIX under biologically relevant conditions. With this model in hand, we also propose how QN, CQ, and amodiaquine (AQ) differ in their ability to inhibit Hz formation.

The first stereoselective total synthesis of quinine

The first entirely stereoselective total synthesis of (-)-quinine is reported.

PHOTOREACTIONS OF QUININE IN AQUEOUS CITRIC ACID SOLUTION. PART 3. PRODUCTS FORMED IN AQUEOUS 2-HYDROXY-2-METHYLPROPIONIC ACID

7'-(2-hydroxyprop-2-yl)-7',8'-dihydroquinine and the corresponding 7',8'-dihydrodeoxyquinine derivative have been identified together with deoxyquinine as products of the irradation of quinine in aqueous 2-hydroxy-2-methylpropionic acid.A cyclised product of 4'-(2-hydroxyprop-2-yl)-1',4'-dihydroquinine was also isolated from the reaction mixture.