Heterocyclic Building Blocks-Quinuclidine

Organocatalytic Enantioselective Cascade Aza-Michael/Michael Addition Sequence for Asymmetric Synthesis of Chiral Spiro[pyrrolidine-3,3′-oxindole]s was written by Zhao, Bo-Liang;Du, Da-Ming. And the article was included in Asian Journal of Organic Chemistry in 2015.Reference of 1256245-79-0 This article mentions the following:

An organocatalytic asym. cascade aza-Michael/Michael addition between tosylaminomethyl enones or enoates and 3-ylideneoxindoles catalyzed by a chiral squaramide that afforded complex and flexible spiro[pyrrolidine-3,3′-oxindole]s was developed. Single-step construction of mols. with three contiguous stereocenters including one quaternary center in excellent yields with highly diastereo- and enantioselectivity are rare and should be useful in medicinal chem. and diversity oriented synthesis of this intriguing class of compounds In the experiment, the researchers used many compounds, for example, 3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1256245-79-0Reference of 1256245-79-0).

3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1256245-79-0) belongs to quinuclidine derivatives. In alkane solvents quinuclidine is a Lewis base that forms adducts with a variety of Lewis acids. The reactions of quinuclidine compounds that lead to opening of the 1-azabi-cyclic system at the N-C and C-C bonds to give piperidine derivatives or, via subsequent rearrangements, derivatives of other heterocyclic systems, are correlated.Reference of 1256245-79-0

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Interfacial adsorption and micellization behaviour of alkaloid based chiral compounds in aqueous medium was written by Maiti, Kajari;Prasad, Madhumita;Chatterjee, Amrita;Bhattacharya, P. K.;Moulik, S. P.. And the article was included in Journal of Surface Science and Technology in 2004.Application In Synthesis of (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride This article mentions the following:

Chiral compounds I, II, III and IV were synthesized and characterized. Their interfacial (at air/solution interface) adsorption and self-association in aqueous medium were studied by tensiometric, conductometric and spectrophotometric methods. The compounds formed micelles in solution with low CMC values. The results were analyzed and thermodn. of the micellization of the chiral compounds and their adsorption at the air/solution interface were evaluated and discussed. In the experiment, the researchers used many compounds, for example, (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3Application In Synthesis of (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride).

(1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3) belongs to quinuclidine derivatives. Quinuclidine acts as a catalyst, a chemical building block and is used in organic synthesis. The reactions of quinuclidine compounds that lead to opening of the 1-azabi-cyclic system at the N-C and C-C bonds to give piperidine derivatives or, via subsequent rearrangements, derivatives of other heterocyclic systems, are correlated.Application In Synthesis of (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Enantioselective synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester (Vinyl-ACCA-OEt) by asymmetric phase-transfer catalyzed cyclopropanation of (E)-N-phenylmethyleneglycine ethyl ester was written by Belyk, Kevin M.;Xiang, Bangping;Bulger, Paul G.;Leonard, William R.;Balsells, Jaume;Yin, Jingjun;Chen, Cheng-yi. And the article was included in Organic Process Research & Development in 2010.Computed Properties of C37H37BrN2O This article mentions the following:

A concise asym. synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid Et ester, a key intermediate in the preparation of many hepatitis C virus inhibitors, is described. Stereoselective cyclopropanation of (E)-N-phenylmethyleneglycine Et ester was effected by treatment with trans-1,4-dibromo-2-butene in the presence of a catalytic amount of a chiral phase-transfer catalyst. Microscale high-throughput experimentation techniques were successfully used to identify a cinchonidine-derived catalyst that provided (1R,2S)-1-(E)-N-phenylmethyleneamino-2-vinylcyclopropanecarboxylic acid Et ester in up to 84% ee. This was translated to a lab scale process to attain 78% yield and 77.4% ee. Chiral purity upgrade and isolation of the ester was accomplished via preparatory supercritical fluid chromatog. followed by crystallization of the ester as its tosylate salt. The improved synthesis described herein represents a potentially more economical preparation of this valuable intermediate. In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3Computed Properties of C37H37BrN2O).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. In alkane solvents quinuclidine is a Lewis base that forms adducts with a variety of Lewis acids. Quinuclidine derivatives can also be formed conveniently by introducing substituents into the quinuclidine ring, but the scope of this method is rather limited by the available source of starting materials.Computed Properties of C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Production at the Curie level of no-carrier-added 6-¹⁸F-fluoro-L-dopa was written by Libert, Lionel C.;Franci, Xavier;Plenevaux, Alain R.;Ooi, Takashi;Maruoka, Keiji;Luxen, Andre J.;Lemaire, Christian F.. And the article was included in Journal of Nuclear Medicine in 2013.Product Details of 200132-54-3 This article mentions the following:

6-¹⁸F-fluoro-L-dopa (¹⁸F-FDOPA) has proven to be a useful radiopharmaceutical for the evaluation of presynaptic dopaminergic function using PET. In comparison to electrophilic synthesis, the no-carrier-added (NCA) nucleophilic method has several advantages. These include much higher available activity and specific activity. Recently, we have described an NCA enantioselective synthesis using a chiral phase-transfer catalyst. However, some chems. were difficult to implement into a com. available synthesizer, restricting access to this radiopharmaceutical to only a few PET centers. Methods: In this paper, 2 important chem. improvements are proposed to simplify production of ¹⁸F-FDOPA, resulting in straightforward automation of the synthesis in a com. available module. Results: First, a fast, simple, and reliable synthesis of 2-¹⁸F-fluoro-4,5-dimethoxybenzyl iodide on a solid-phase support was developed. Second, a phase-transfer catalyst alkylation of a glycine derivative at room temperature was used to enable enantioselective carbon-carbon bond formation. After hydrolysis and high-performance liquid chromatog. purification, a high enantiomeric excess of ¹⁸F-FDOPA (鈭?7%) was obtained using a chiral catalyst available from a biphenyl 3 substrate. The total synthesis time was 63 min, and the decay-corrected radiochem. yield was 36% 卤 3% (n = 8). Conclusion: By exploiting the advantages of this NCA approach, using a starting activity of 185 GBq of NCA ¹⁸F-fluoride, high activities of ¹⁸F-FDOPA (>45 GBq) with high specific activity (鈮?53 GBq/渭mol) are now available at the end of synthesis for use in clin. investigations. In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3Product Details of 200132-54-3).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. In alkane solvents quinuclidine is a Lewis base that forms adducts with a variety of Lewis acids. Quinuclidine derivatives can also be formed conveniently by introducing substituents into the quinuclidine ring, but the scope of this method is rather limited by the available source of starting materials.Product Details of 200132-54-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Enantioselective synthesis of ammonium cations was written by Walsh, Mark P.;Phelps, Joseph M.;Lennon, Marc E.;Yufit, Dmitry S.;Kitching, Matthew O.. And the article was included in Nature (London, United Kingdom) in 2021.Reference of 69221-14-3 This article mentions the following:

Here showed that control of the chirality of ammonium cations was easily achieved through a supramol. recognition process. By combining enantioselective ammonium recognition mediated by 1,1′-bi-2-naphthol scaffolds with conditions that allow the nitrogen stereocentre to racemize, chiral ammonium cations could be produced in excellent yields and selectivities. Mechanistic investigations demonstrate that, through a combination of solution and solid-phase recognition, a thermodynamically driven adductive crystallization process was responsible for the observed selectivity. Distinct from processes based on dynamic and kinetic resolution, which were under kinetic control, this allows for increased selectivity over time by a self-corrective process. The importance of nitrogen stereocentres could be revealed through a stereoselective supramol. recognition, which was not possible with naturally occurring pseudoenantiomeric Cinchona alkaloids. In the experiment, the researchers used many compounds, for example, (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3Reference of 69221-14-3).

(1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3) belongs to quinuclidine derivatives. Quinuclidine exists in a number of naturally occurring compounds, biologically active agents, and privileged catalysts and ligands for asymmetric catalysis. As a ligand, quinuclidine is useful in the studies of OsO4-catalyzed dihydroxylation of olefins. It plays an important role in the formation of onium salts used testing of PAC-antagonist activity.Reference of 69221-14-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Diastereoselective Aziridination of Chiral Electron-Deficient Olefins with N-Chloro-N-sodiocarbamates Catalyzed by Chiral Quaternary Ammonium Salts was written by Murakami, Yuta;Takeda, Youhei;Minakata, Satoshi. And the article was included in Journal of Organic Chemistry in 2011.Application of 200132-54-3 This article mentions the following:

Chiral quaternary ammonium salt-catalyzed diastereoselective aziridination of electron-deficient olefins that possess a chiral auxiliary with N-chloro-N-sodiocarbamates was developed. The key to high stereoselectivity was found to be the employment of the “matching” stereochem. combination of chiral auxiliary/ammonium salt. For example, when 3-phenyl-(4R,7S)-4-methyl-7-isopropyl-4,5,6,7-tetrahydroindazole (L-menthopyrazole) as a chiral auxiliary and a cinchonidine-derived chiral ammonium salt as a catalyst were applied to the reaction system, perfect diastereoselectivity was realized. Furthermore, the preparation of enantiomerically pure aziridines by removal of the chiral auxiliary was demonstrated. In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3Application of 200132-54-3).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. Quinuclidine acts as a catalyst, a chemical building block and is used in organic synthesis. The configuration at C-8 (quinuclidine attachment) and C-9 position (bearing hydroxy group) are important as they help in the orientation of hydroxy group and nitrogen atom of quinuclidine.Application of 200132-54-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Highly Enantioselective Addition of N-2,2,2-Trifluoroethylisatin Ketimines to Ethylene Sulfonyl Fluoride was written by Chen, Jie;Zhu, Dong-yu;Zhang, Xue-jing;Yan, Ming. And the article was included in Journal of Organic Chemistry in 2021.Product Details of 1256245-79-0 This article mentions the following:

An enantioselective Michael addition between N-2,2,2-trifluoroethylisatin ketimines I (R¹ = Me, allyl, Bn, etc.; R² = H, 7-Cl, 6-Cl, 5,7-(CH₃)₂, etc.) and ethylene sulfonyl fluoride has been disclosed. This method provides a facile strategy to access a range of structurally diverse isatin-derived 伪-(trifluoromethyl)imine derivatives II with excellent yields and enantioselectivities. The intriguing combination of 伪-(trifluoromethyl)amine and sulfonyl fluoride groups leads to the valuable candidates for the drug discovery. In the experiment, the researchers used many compounds, for example, 3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1256245-79-0Product Details of 1256245-79-0).

3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1256245-79-0) belongs to quinuclidine derivatives. Quinuclidine acts as a catalyst, a chemical building block and is used in organic synthesis. Traditionally, quinuclidine scaffolds can be constructed by second-order nucleophilic substitution (SN2) reaction or condensation reaction of piperidine derivatives. However, most of these reactions are racemic or chiral auxiliary-assisted processes.Product Details of 1256245-79-0

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Enantioselective Phase-Transfer Catalyzed 伪-Sulfanylation of Isoxazolidin-5-ones: An Entry to 尾^2,2-Amino Acid Derivatives was written by Cadart, Timothee;Berthonneau, Clement;Levacher, Vincent;Perrio, Stephane;Briere, Jean-Francois. And the article was included in Chemistry – A European Journal in 2016.COA of Formula: C37H37BrN2O This article mentions the following:

An unprecedented enantioselective 伪-functionalization of C4-substituted N-alkoxycarbonyl isoxazolidin-5-ones, readily available platforms from Meldrum’s acid derivatives, by N-sulfanylphthalimide (PhthSR) electrophiles was achieved upon an efficient phase-transfer catalytic approach, mediated by a com. N-spiro quaternary ammonium catalyst. Two catalytic activities of the in situ formed R₄N⁺Phth^– species were highlighted, the phtalimidate being involved in the anion metathesis event and likely as a Bronsted base. This sequence offers a straightforward access to 伪,伪-disubstituted isoxazolidinones, which turned out to be useful precursors of 伪-sulfanyl-尾^2,2-amino acid derivatives In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3COA of Formula: C37H37BrN2O).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. Quinuclidine acts as a catalyst, a chemical building block and is used in organic synthesis. Asymmetric construction of quinuclidine derivatives has been realized by an iridium-catalyzed allylic dearomatization reaction. The catalytic system, derived from [Ir(cod)Cl]2 and the Feringa ligand, tolerates a broad range of substrates. A large array of quinuclidine derivatives can be obtained under mild conditions in good to excellent yields (68%鈥?6%), diastereoselectivity (up to >20/1 dr), and enantioselectivity (up to >99% ee).COA of Formula: C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Highly enantioselective monofluoromethylation of C2-arylindoles using FBSM under chiral phase-transfer catalysis was written by Matsuzaki, Kohei;Furukawa, Tatsuya;Tokunaga, Etsuko;Matsumoto, Takashi;Shiro, Motoo;Shibata, Norio. And the article was included in Organic Letters in 2013.Reference of 69221-14-3 This article mentions the following:

The highly enantioselective addition of 1-fluoro-1,1-bis(phenylsulfonyl)methane (FBSM) to vinylogous imines generated in situ from 2-aryl-3-(1-arylsulfonylmethyl)indoles was achieved using chiral ammonium salts derived from cinchona alkaloids. One-pot conversion from 2-arylindoles e. g., I with FBSM was also adaptable under the same reaction conditions. The key for this transformation is the effective use of the arylsulfonyl group. In the experiment, the researchers used many compounds, for example, (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3Reference of 69221-14-3).

(1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3) belongs to quinuclidine derivatives. The development of synthetic approaches for efficient construction of novel quinuclidine derivatives is of great significance. Carbamoyl boranes are generally prepared as adducts with tertiary amines, such as trialkyl amines, pyridine, or quinuclidine, via two synthetic approaches based either on amidation of amine-carboxyborane adducts or on hydrolysis of amine-cyanoboranes.Reference of 69221-14-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Polymeric pseudo-liquid membranes from polymethacrylate derivative bearing oligodimethylsiloxane unit was written by Tsujimoto, Hiroki;Yoshikawa, Masakazu. And the article was included in Journal of Membrane and Separation Technology in 2017.Formula: C37H37BrN2O This article mentions the following:

Novel liquid membrane system, which is named polymeric pseudo-liquid membrane was constructed from polymethacrylate derivative bearing oligodimethylsiloxane (PDMSMA), showing rubbery state under operating conditions, as a membrane matrix. In the present study, dibenzo-18-crown-6 (DB18C6), dibenzo-21-crown-7 (DB21C7) or O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide (AMCC) was adopted as a carrier for KCl transport, CsCl transport or optical resolution of racemic mixture of phenylglycine (Phegly), resp. The results of KCl and CsCl transports revealed that the membrane transport was attained by carrier-diffusion mechanism like conventional liquid membranes. The present study led the conclusion that PDMSMA can be applicable not only to membrane transport of alkali metal ions, such as K⁺ and Cs⁺, but also to chiral separation In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3Formula: C37H37BrN2O).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. Quinuclidine derivatives are also widely utilized as homogeneous or heterogeneous catalysts in various asymmetric processes such as Morita鈥揃aylis鈥揌illman reactions, Sharpless dihydroxylation reactions, and phase-transfer catalytic reactions. As a ligand, quinuclidine is useful in the studies of OsO4-catalyzed dihydroxylation of olefins. It plays an important role in the formation of onium salts used testing of PAC-antagonist activity.Formula: C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider