14528-53-1

Basic information

• Product Name: 6'-methoxycinchonan-9-one
• Synonyms: 6'-methoxycinchonan-9-one;(8R)-6'-Methoxycinchonan-9-one;Einecs 238-549-5
• CAS NO: 14528-53-1
• Molecular Formula: C₂₀H₂₂N₂O₂
• Molecular Weight: 322.40088
• EINECS: 238-549-5
• Mol File: 14528-53-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 477.8°Cat760mmHg
• Flash Point: 242.8°C
• Appearance: /
• Density: 1.21g/cm³
• PKA: 7.45±0.70(Predicted)
• CAS DataBase Reference: 6'-methoxycinchonan-9-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6'-methoxycinchonan-9-one(14528-53-1)
• EPA Substance Registry System: 6'-methoxycinchonan-9-one(14528-53-1)

Safety Data

• Hazardous Substances Data: 14528-53-1(Hazardous Substances Data)

Usage

General Description

6'-Methoxycinchonan-9-one is a chemical compound that belongs to the class of cinchona alkaloids. It is a derivative of quinine, which is a well-known antimalarial drug. 6'-Methoxycinchonan-9-one has been studied for its potential pharmacological activities, including antimalarial, antifungal, and anticancer properties. It is also used in organic chemistry as a chiral auxiliary in asymmetric synthesis. The compound's structure and properties make it a valuable target for research and development in the pharmaceutical and chemical industries.

Upstream product

• 119-61-9 benzophenone 
• 130-95-0 Quinine 
• 486-25-9 9-fluorenone 
• 56-54-2 quinine 
• 908578-83-6 N-bromoquinotoxine 
• 56-54-2 quinindine 
• 56-54-2 (6-Methoxy-quinolin-4-yl)-((1S,2S,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol 
• 56-54-2 quinidine 
• 64-19-7 acetic acid 
• 56-54-2 9-epiquinine 

Downstream Products

• 56-54-2 9-epiquinine 
• 56-54-2 quinidine 
• 130-95-0 Quinine 
• 56-54-2 quinine 
• 130-95-0 quinine 
• 56-54-2 quinine 
• 1393601-64-3 (8R,9S)-6'-methoxy-9-phenyl-9-cinchonanol 
• 1393601-69-8 (8S,9R)-6'-methoxy-9-phenyl-9-cinchonanol 
• 1393601-66-5 (8R,9S)-6'-methoxy-9-(3-aminophenyl)-9-cinchonanol 
• 52346-11-9 tert-butyl 2-[(3R,4S)-3-ethenylpiperidin-4-yl]acetate 
• 86-68-0 6-methoxyquinoline-4-carboxylic acid 

Relevant articles and documents

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Diastereoselective Corey-Chaykovsky 9-epoxymethylation of cinchona alkaloids: Access to chiral scaffolds with diverse functionalities

Reaction of dimethylsulfonium methylide with Cinchona alkaloid ketones proceeds with complete diastereoselectivity to give epoxides of 8,9-like configuration. The reaction of dimethylsulfoxonium methylide gives different isomers, albeit with lower (4:1) selectivity. α-Epimerization of the alkaloid ketones resulted in formation of two separable diasteromeric products. The configurations of the epoxides were elucidated on the basis of NMR data combined with DFT calculations. Models explaining observed selectivity are discussed. The epoxides were efficiently transformed to a number of derivatives through selective SN2-type ring-opening reactions with various nucleophiles, often without the need of additional purification steps.

Rabe rest in peace: Confirmation of the rabe-kindler conversion of d-quinotoxine into quinine: Experimental affirmation of the woodward-doering formal total synthesis of quinine

(Chemical Equation Presented) Put to rest: The three-step conversion of d-quinotoxine into quinine, as originally reported by Rabe and Kindler in 1918, has been experimentally verified. This conversion serves to reaffirm the formal total synthesis of quin