32531-66-1

Basic information

• Product Name: 2-(DIPHENYLMETHYL)-QUINUCLIDIN-3-ONE
• Synonyms: 2-(DIPHENYLMETHYL)-QUINUCLIDIN-3-ONE;2-benzhydrylquinuclidin-3-one(WXG03235)
• CAS NO: 32531-66-1
• Molecular Formula: C₂₀H₂₁NO
• Molecular Weight: 291.39
• Mol File: 32531-66-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 432.8°C at 760 mmHg
• Flash Point: 163.2°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 1.08E-07mmHg at 25°C
• Refractive Index: 1.628
• PKA: 6.19±0.40(Predicted)
• Water Solubility: 26mg/L at 25℃
• CAS DataBase Reference: 2-(DIPHENYLMETHYL)-QUINUCLIDIN-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(DIPHENYLMETHYL)-QUINUCLIDIN-3-ONE(32531-66-1)
• EPA Substance Registry System: 2-(DIPHENYLMETHYL)-QUINUCLIDIN-3-ONE(32531-66-1)

Safety Data

• Hazardous Substances Data: 32531-66-1(Hazardous Substances Data)

Usage

Description

2-(DIPHENYLMETHYL)-QUINUCLIDIN-3-ONE is a chemical compound with the molecular formula C28H29NO. It is a quinuclidine derivative that acts as a potent and selective negative allosteric modulator of the muscarinic acetylcholine M1 receptor. 2-(DIPHENYLMETHYL)-QUINUCLIDIN-3-ONE has been studied for its potential therapeutic applications, particularly in the treatment of conditions such as Alzheimer's disease and schizophrenia, where modulation of the M1 receptor has shown promise. Research has also focused on its potential role in cognitive enhancement and improving memory function. As a negative allosteric modulator, it blocks the binding of acetylcholine to the M1 receptor, thereby altering its activity and potentially leading to beneficial effects in specific brain functions.

Uses

Used in Pharmaceutical Industry:
2-(DIPHENYLMETHYL)-QUINUCLIDIN-3-ONE is used as a therapeutic agent for the treatment of neurological disorders such as Alzheimer's disease and schizophrenia. Its modulation of the M1 receptor has shown promise in managing the symptoms and progression of these conditions.
Used in Cognitive Enhancement:
2-(DIPHENYLMETHYL)-QUINUCLIDIN-3-ONE is used as a cognitive enhancer to improve memory function. By blocking the binding of acetylcholine to the M1 receptor, it can potentially lead to beneficial effects on specific brain functions, enhancing cognitive performance.
Used in Research and Development:
2-(DIPHENYLMETHYL)-QUINUCLIDIN-3-ONE is used as a research compound for studying the role of the M1 receptor in various cognitive and neurological processes. This can help in the development of new therapeutic strategies and interventions for related conditions.

InChI:InChI=1/C20H21NO/c22-20-17-11-13-21(14-12-17)19(20)18(15-7-3-1-4-8-15)16-9-5-2-6-10-16/h1-10,17-19H,11-14H2

Upstream product

• 24123-89-5 2-benzylidene-3-quinuclidinone 
• 100-58-3 phenylmagnesium bromide 
• 100-59-4 phenylmagnesium chloride 
• 1193-65-3 3-quinuclidinone hydrochloride 
• 24123-89-5 (Z)-2-benzylidene-1-azabicyclo[2.2.2]octan-3-one 
• 100-52-7 benzaldehyde 
• 3731-38-2 3-Quinuclidinone 

Downstream Products

• 52321-77-4 (+/-)-cis-2-(diphenylmethyl)-1-azabicyclo<2.2.2>octan-3-ol 
• 32531-19-4 (-)-cis-2-(diphenylmethyl)-1-azabicyclo<2.2.2>octan-3-amine 
• 141958-08-9 2-(diphenylmethyl)-N-<(2-methoxyphenyl)methyl>-1-azabicyclo<2.2.2>octan-3-imine 
• 683206-53-3 (S)-2-diphenylmethylquinuclidin-3-one 
• 142035-23-2 (-)-(2S,3S)-cis-2-(diphenylmethyl)-1-azabicyclo[2.2.2]octane-3-amine 
• 683206-54-4 (2S)-benzhydryl-3-quinuclidinone L-tartaric acid salt 
• 129912-34-1 (2S,3S/2R,3R)-cis-2-(diphenylmethyl)-N-((2-methoxyphenyl)methyl)-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride 
• 129912-34-1 (+/-)-CP 93846 
• 141957-98-4 cis-2-(diphenylmethyl)-N-<(2-ethoxyphenyl)methyl>-1-azabicyclo<2.2.2>octan-3-amine 
• 141958-04-5 cis-2-(diphenylmethyl)-N-<(2-methoxyphenyl)methyl>-N-methyl-1-azabicyclo<2.2.2>octan-3-amine 
• 129912-36-3 cis-2-(diphenylmethyl)-N-<(4-methoxyphenyl)methyl>-1-azabicyclo<2.2.2>octan-3-amine 
• 129912-43-2 cis-2-(diphenylmethyl)-N-<(3-methoxyphenyl)methyl>-1-azabicyclo<2.2.2>octan-3-amine 

Relevant articles and documents

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.

Preparation method of quinuclidine-containing compound

The present invention relates to a preparation method of a quinuclidine-containing compound, and the method comprises the following steps: 1) reacting compound IIIa, compound IV with L-camphorsulfonicacid to form compound VIb; and 2) reacting the compound VIb obtained in the step 1) with L-camphorsulfonic acid to obtain compound VIa. The preparation method has mild reaction conditions, easy operation and simple post-treatment. During the reaction, by simple changing of the feeding order, the amounts of a reducing agent and a Lewis acid used are greatly reduced, and the temperature control range is more extensive during the feeding process. In addition, through reaction of the L-camphorsulfonic acid and an isomer mixture, a product with high optical purity can be obtained by simple recrystallization operation, the ee value of a target configuration can be as high as 99.3%, and the method is suitable for promotion in industry.

Overcoming chloroquine resistance in malaria: Design, synthesis and structure-activity relationships of novel chemoreversal agents

Malaria remains a significant infectious disease with even artemisinin-based therapies now facing resistance in the field. Development of new therapies is urgently needed, either by finding new compounds with unique modes of action, or by reversing resistance towards known drugs with 'chemosensitizers' or 'chemoreversal' agents (CRA). Concerning the latter, we have focused on the resistance mechanisms developed against chloroquine (CQ). We have synthesized a series of compounds related to previously identified CRAs, and found promising novel compounds. These compounds show encouraging results in a coumarin labeled chloroquine uptake assay, exhibiting a dose response in resensitising parasites to the antimalarial effects of chloroquine. Selected compounds show consistent potency across a panel of chloroquine and artemisinin sensitive and resistant parasites, and a wide therapeutic window. This data supports further study of CRAs in the treatment of malaria and, ultimately, their use in chloroquine-based combination therapies.