139237-97-1

Basic information

• Product Name: (S)-((2R)-5-ethylidene-1-azabicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinoline-4-yl)-methanol
• CAS NO: 139237-97-1
• Molecular Weight: 324.423
• Mol File: 139237-97-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S)-((2R)-5-ethylidene-1-azabicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinoline-4-yl)-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-((2R)-5-ethylidene-1-azabicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinoline-4-yl)-methanol(139237-97-1)
• EPA Substance Registry System: (S)-((2R)-5-ethylidene-1-azabicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinoline-4-yl)-methanol(139237-97-1)

Safety Data

• Hazardous Substances Data: 139237-97-1(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 56-54-2 quinidine 
• 53922-99-9 α-10-bromodihydroquinidine 
• 56-54-2 quinindine 
• 4363-94-4 6-methoxyquinoline-4-carbaldehyde 
• 56-54-2 (+)-quinidine 

Downstream Products

• 53467-23-5 3-hydroxyquinidine 
• 60761-51-5 (3R)-3-hydroxyquinidine 
• 60723-44-6 (3S)-3-hydroxyquinidine 9-benzoate 
• 60723-43-5 (8R,9S)-6'-methoxy-3-oxoruban-9-yl acetate 
• 139239-49-9 apoquinidine methyl ether 9-acetate 

Relevant articles and documents

(3S)-3-Hydroxyquinidine, the Major Biotransformation Product of Quinidine. Synthesis and Conformational Studies. X-Ray Molecular Structure of (3S)-3-Hydroxyquinidine Methanesulphonate

(3S)-3-Hydroxyquinidine, the major metabolite of the Cinchona alkaloid quinidine, was prepared by synthetic chemical modification or microbial oxidation of quinidine.The structure of this metabolite has been demonstrated to be (3S)-3-hydroxyquinidine by 1H and 13C NMR, IR, UV and mass spectral analysis.Previously published comparisons of the 13C NMR spectra of 3-hydroxyquinidine and model compounds were used to establish the absolute stereochemistry of the metabolite (see ref. 8).This assignment has been verified by single-crystal X-ray analysis of (3S)-3-hydroxyquinidine methanesulphonate.The gas- and solution-phase conformational preference of the metabolite derived from molecular modelling and NOE studies are compared with the conformation observed by X-ray crystallography.

Positional isomerization of quinine and quinidine via rhodium on alumina catalysis: Practical one-step synthesis of Δ3,10-isoquinine and Δ3,10-isoquinidine

The synthesis of Δ3,10-isoquinine (5Z,5E) and Δ3,10-isoquinidine (6Z,6E) was achieved in one-step through positional isomerization of the terminal alkene in the parent cinchona alkaloids using catalytic amounts of 5% Rh/Al2O3 and excess hydrochloric acid in refluxing 50% aqueous EtOH. The products were obtained in good yields as a mixture of E and Z geometric isomers and fully characterized using spectroscopic methods.

Hydrogenation of prochiral ketones

Process for enantioselectively hydrogenating prochiralen ketones to (S)-alcohols using platinum catalysts in the presence of cinchonines or quinidines as modifiers and in the presence of hydrogen, which is characterized in that the modifiers used are cinchonines unsubstituted in the 3-position, 3-ethylidenyl- or 9-methoxycinchonines or derivatives thereof in which the quinoline ring is replaced by other rings.