24123-89-5

Basic information

• Product Name: 2-benzylidene-1-azabicyclo[2.2.2]octan-3-one
• Synonyms: 1-azabicyclo[2.2.2]octan-3-one, 2-(phenylmethylene)-; 2-Benzylidenequinuclidin-3-one
• CAS NO: 24123-89-5
• Molecular Formula: C₁₄H₁₅NO
• Molecular Weight: 213.275
• Mol File: 24123-89-5.mol

Chemical Properties

• Boiling Point: 388.2°C at 760 mmHg
• Flash Point: 159.3°C
• Density: 1.17g/cm³
• Vapor Pressure: 3.12E-06mmHg at 25°C
• Refractive Index: 1.616
• CAS DataBase Reference: 2-benzylidene-1-azabicyclo[2.2.2]octan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-benzylidene-1-azabicyclo[2.2.2]octan-3-one(24123-89-5)
• EPA Substance Registry System: 2-benzylidene-1-azabicyclo[2.2.2]octan-3-one(24123-89-5)

Safety Data

• Hazardous Substances Data: 24123-89-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Benzylidene-1-azabicyclo[2.2.2]octan-3-one is used as a potential pharmacological agent for various therapeutic applications. Its unique molecular structure allows it to be a promising candidate for drug design and development, with studies showing its potential in treating various medical conditions.
Used in Medicinal Chemistry Research:
2-Benzylidene-1-azabicyclo[2.2.2]octan-3-one is used as a subject of active research in medicinal chemistry. Its unique molecular structure and potential biological and pharmacological activities make it an interesting compound to study and develop for future drug applications.

Upstream product

• 3731-38-2 3-Quinuclidinone 
• 100-52-7 benzaldehyde 
• 1193-65-3 3-quinuclidinone hydrochloride 

Downstream Products

• 78961-51-0 4-<(3'-Indolyl)benzyl>-3-hydroxyquinuclidine 
• 52455-72-8 2-benzylidenequinuclidin-3-one 
• 172035-65-3 2-(1,2-diphenylethyl)-3-oxo-1-azabicyclo<2.2.2>octane 
• 78961-46-3 syn-(E)-2-phenylmethylene-3-quinuclidone oxime hydrochloride 
• 78130-07-1 anti-(Z)-2-phenylmethylene-3-quinuclidone oxime 
• 78121-28-5 syn-(Z)-2-phenylmethylene-3-quinuclidone oxime 
• 716-79-0 2-phenyl-1H-benzoimidazole 
• 81164-27-4 3,5-diphenyl-1,6-diazatricyclo[6.2.2.0^2,7]dodeca-2⁽⁷⁾,3,5-triene 

Relevant articles and documents

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.

QUINOLINE DERIVATIVES USEFUL AS TYROSINE KINASE INHIBITORS

Disclosed are imidazole compounds, as well as pharmaceutical compositions and methods of use thereof. One embodiment is a compound having the structure (I) and pharmaceutically acceptable salts, prodrugs and N-oxides thereof (and solvates and hydrates thereof), wherein R1, X, Y1, Y2, Y3 and Z are as described herein. In certain embodiments, a compound disclosed herein inhibits a cellular TAM receptor, and can be used to treat disease mediated by or involving the TAM receptor family.

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.

Scale-up of an enantioselective Overman rearrangement for an asymmetric synthesis of a glycine transporter 1 inhibitor

An enantioselective Overman 3,3-sigmatropic rearrangement on a quinuclidine skeleton was developed for the pilot-plant synthesis of a glycine transporter 1 inhibitor. The first stereocenter was produced by a Ru-catalyzed asymmetric transfer hydrogenation process followed by chirality transfer using the Overman rearrangement. The second stereocenter was generated by a diastereoselective hydrogenation reaction.

BRIDGED BICYCLIC HETEROARYL SUBSTITUTED TRIAZOLES USEFUL AS AXL INHIBITORS

Bridged bicyclic heteroaryl substituted triazoles and pharmaceutical compositions containing the compounds are disclosed as being useful in inhibiting the activity of the receptor protein tyrosine kinase AxI. Methods of using the compounds in treating diseases or conditions associated with AxI activity are also disclosed

POLYCYCLIC ARYL SUBSTITUTED TRIAZOLES AND POLYCYCLIC HETEROARYL SUBSTITUTED TRIAZOLES USEFUL AS AXL INHIBITORS

Polycyclic aryl and polycyclic heteroaryl substituted triazoles and pharmaceutical compositions containing the compounds are disclosed as being useful in inhibiting the activity of the receptor protein tyrosine kinase Axl. Methods of using the compounds in treating diseases or conditions associated with Axl catalytic activity are also disclosed.

BRIDGED BICYCLIC ARYL AND BRIDGED BICYCLIC HETEROARYL SUBSTITUTED TRIAZOLES USEFUL AS AXL INHIBITORS

Bridged bicyclic aryl or heteroaryl substituted triazoles and pharmaceutical compositions containing the compounds are disclosed as being useful in inhibiting the activity of the receptor protein tyrosine kinase Axl. Methods of using the compounds in treating diseases or conditions associated with Axl activity are also disclosed.

Synthetic entry to tricyclic and tetracyclic quinuclidine derivatives by cycloaddition and ring transformation

The (Z)-2-arylidene-quinuclidines 5-8 were synthesized. Their reaction with aliphatic dibasic functional reagents in both basic and acidic conditions afforded the fused heterocycles 9, 10 and 11. However, the reaction of arylidene derivative 5 with an aromatic dibasic functional reagent gave benzimidazole 13 in lieu of the anticipated tetracyclic system, quinuclidino[3,2-e]benzo[b]-1,4- diazepine 12. Cycloadditions of 5 with different reagents gave the heterocyclic derivatives 17, 19, 22 and 23. Acid-catalyzed cyclization of 5 with excess resorcinol gave 24. Compounds 9a, 19 and 24 showed antibacterial activities.