207129-36-0

Usage

Uses

Used in Medicinal Chemistry:
Quincoridine is used as a valuable building block for medicinal chemistry, providing a foundation for the development of new pharmaceutical compounds.
Used in Asymmetric Synthesis:
Quincoridine is used as a chiral ligand in asymmetric synthesis, enabling the creation of enantiomerically pure compounds, which are crucial in various pharmaceutical applications.
Used in Chiral Separation Techniques:
Quincoridine is used as a resolving agent and chiral stationary phase in chromatographic techniques, aiding in the separation of enantiomers and improving the purity of chiral compounds.

InChI:InChI=1/C10H17NO/c1-2-8-6-11-4-3-9(8)5-10(11)7-12/h2,8-10,12H,1,3-7H2/t8-,9-,10+/m0/s1

Upstream product

• 73627-88-0 (1R,2R,1'S,2'R,5'S)-cyclohex-4-ene-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester 
• 1312224-59-1 1-((2S,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-4,5-bis(2-iodoethyl)-piperidin-1-yl)-2,2,2-trifluoroethanone 
• 956006-37-4 ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(iodomethyl)cyclohexylmethoxy)(tert-butyl)dimethylsilane 
• 956006-05-6 ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)cyclohexyl)methanol 
• 956006-36-3 ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(hydroxymethyl)cyclohexyl)methanol 
• 956006-03-4 (1R,2R,4R,5R)-bis((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 4,5-bis(benzyloxy)cyclohexane-1,2-dicarboxylate 
• 956006-35-2 (1R,2R,4R,5R)-bis((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 4-(benzyloxy)-5-hydroxycyclohexane-1,2-dicarboxylate 
• 956006-34-1 (1S,3R,4R,6R)-3-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 4-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylate 
• 1312224-71-7 C₁₆H₃₃NO₂Si 
• 1312224-70-6 1-((2S,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-4-(2-hydroxyethyl)-5-vinylpiperidin-1-yl)-2,2,2-trifluoroethanone 
• 1312224-69-3 C₂₀H₃₄F₃NO₄Si 
• 1312224-58-0 2-((3R,4R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-4-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-3-yl)ethyl acetate 
• 1312224-67-1 2-((3R,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-4-yl)ethyl acetate 
• 1312224-57-9 1-((2S,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-4,5-bis(2-hydroxyethyl)-piperidin-1-yl)-2,2,2-trifluoroethanone 

Downstream Products

• 219794-79-3 ((2S,4S,5R)-5-Ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol 
• 219794-68-0 10,11-didehydroquincorine 

Relevant academic research and scientific papers

Scope of stereoselective Mn-mediated radical addition to chiral hydrazones and application in a formal synthesis of quinine

Stereocontrolled Mn-mediated addition of alkyl iodides to chiral N-acylhydrazones enables strategic C-C bond constructions at the stereogenic centers of chiral amines. Applying this strategy to quinine suggested complementary synthetic approaches to construct C-C bonds attached at the nitrogen-bearing stereogenic center using multifunctional alkyl iodides 6a-d as radical precursors, or using multifunctional chiral N-acylhydrazones 26a-d as radical acceptors. These were included among Mn-mediated radical additions of various alkyl iodides to a range of chiral N-acylhydrazone radical acceptors, leading to the discovery that pyridine and alkene functionalities are incompatible. In a revised strategy, these functionalities are avoided during the Mn-mediated radical addition of 6d to chiral N-acylhydrazone 22b, which generated a key C-C bond with complete stereochemical control at the chiral amine carbon of quinine. Subsequent elaboration included two sequential cyclizations to complete the azabicyclo[2.2.2]octane ring system. Group selectivity between two 2-iodoethyl groups during the second cyclization favored an undesired azabicyclo[3.2.1]octane ring system, an outcome that was found to be consistent with transition state calculations at the B3LYP/6-31G(d) level. Group differentiation at an earlier stage enabled an alternative regioconvergent pathway; this furnished the desired azabicyclo[2.2.2]octane ring system and afforded quincorine (21b), completing a formal synthesis of quinine.

Intermolecular radical addition to N-acylhydrazones as a stereocontrol strategy for alkaloid synthesis: Formal synthesis of quinine

Stereocontrolled Mn-mediated radical addition of alkyl iodides to chiral N-acylhydrazones enables strategic C-C bond disconnection of chiral amines. This strategy was examined in the context of a total synthesis of quinine, generating new findings of functional group compatibility leading to a revised strategy. Completion of a formal synthesis of quinine is presented, validating the application of Mn-mediated radical addition as a useful new C-C bond construction method for alkaloid synthesis. The Mn-mediated addition generates the chiral amine substructure of quinine with complete stereocontrol. Subsequent elaboration includes two successive ring closures to forge the azabicyclo[2.2.2]octane ring system of quincorine, linked to quinine through two known reactions.