24782-61-4

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 3731-38-2 3-Quinuclidinone 
• 1193-65-3 3-quinuclidinone hydrochloride 

Downstream Products

• 852476-87-0 2-(4-fluorobenzyl)quinuclidin-3-one 
• 24802-69-5 2-(bis(4-fluorophenyl)methyl)quinuclidin-3-one 
• 209863-79-6 2-[1-(4-Fluoro-phenyl)-meth-(E)-ylidene]-1-aza-bicyclo[2.2.2]octan-3-one 

Relevant academic research and scientific papers

Aminations and arylations by direct C-O activation for the design of 7,8-dihydro-6H-5,8-ethanopyrido[3,2-d]pyrimidines

The design of some novel disubstituted 7,8-dihydro-6H-5,8-ethanopyrido[3,2-d]pyrimidine derivatives is reported. The series was developed from quinuclidinone, which afforded versatile platforms bearing one lactam function in positionC-2 that were then used to create C-N or C-C bonds for SNAr or palladium-catalyzed cross-coupling reactions byin situC-O activation. The reaction conditions were optimized under microwave irradiation, and a wide range of amines or boronic acids were used to determine the scope and limitations of each method. To complete this study, the X-ray crystallographic data of 7,8-dihydro-6H-5,8-ethanopyrido[3,2-d]pyrimidine derivative49were used to formally establish the structures of the products.

Ruthenium-Catalyzed Highly Enantioselective Synthesis of cis-3-Quinuclidinols via DKR Asymmetric Transfer Hydrogenation

A method for the enantioselective synthesis of cis-3-quinuclidinols by Ru-catalyzed asymmetric transfer hydrogenation via dynamic kinetic resolution is described. The reaction proceeded under mild conditions using ammonium formate as the hydrogen donor, affording the products in high yields (up to 99%) with excellent diastereoselectivity (up to 99:1 dr) and enantioselectivity (95-99% ee). This protocol was applicable to gram-scale preparation with perfect enantioselectivity through simple recrystallization.

Synthesis and Pharmacological Evaluation of Novel Pyrazolyl Piperidine Derivatives as Effective Antiplatelet Agents

The synthesis and antiplatelet activity of substituted pyrazolyl piperidine derivatives (3a–n) are described. These compounds were synthesized by an improved ring opening reaction of 2-arylidene quinuclidinone using hydrazine hydrate under mild conditions

2-(Arylmethyl)-3-substituted quinuclidines as selective α7 nicotinic receptor ligands

A series of 2-(arylmethyl)-3-substituted quinuclidines was developed as α7 neuronal nicotinic acetylcholine receptor (nAChR) agonists based on a putative pharmacophore model. The series is highly selective for the α7 over other nAChRs (e.g., the α4β2 of the CNS, and the muscle and ganglionic subtypes) and is functionally tunable at α7. One member of the series, (+)-N-(1-azabicyclo[2.2.2]oct-3-yl)benzo[b]furan-2-carboxamide (+)-8l), has potent agonistic activity for the α7 nAChR (EC50 = 33 nM, Imax = 1.0), at concentrations below those that result in desensitization.

Mutual Z-/E-isomerization of ferrocenylmethylene- and arylidene-substituted carbo- and heterocycles

The treatment of Z-2-ferrocenylmethylene-, Z-2-arylidene-3-quinuclidinones and 3-methylene-quinuclidines, as well as E-3-ferrocenylmethylenecamphor, -menthone, and -cyclohexanone with NaBPh4 in acetic acid results in their reversible Z-/E-isomerization. The reaction proceeds via hydroxyallyl and crotyl carbocations with a fixed s-cis-conformation.

Quinuclidine chemistry. 2. Synthesis and antiinflammatory properties of 2 substituted benzhydryl 3 quinuclidinols

A number of 2 benzhydryl 3 quinuclidinols were tested for their anti inflammatory activity. The cis isomers were prepared selectively by aluminum isopropoxide reduction of the ketones which were made by the addition of aromatic Grignard reagents to 2 benzylidene 3 quinuclidinones. The most active compound was cis 2 (4,4' difluorobenzhydryl) 3 quinuclidinol. The trans alcohol was less active than the cis isomer. It was made by selectively oxidizing the cis alcohol in a mixture of cis and trans alcohols (formed by NaBH4 reduction of the ketone) followed by chromatography. The two diastereoisomers of the monofluorinated alcohol, 2 (4 fluorobenzhydryl) 3 quinuclidinol, showed activity but were markedly less active than the difluorinated alcohol. The quinuclidine nitrogen was vital for activity for cis 3 (4,4 difluorobenzhydryl) bicyclo [2.2.2] octan 2 one showed only marginal activity.