Month: February 2023

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

A remarkably efficient phase-transfer catalyzed amination of 伪-bromo-伪, 尾-unsaturated ketones in water was written by Mekonnen, Alemayehu;Tesfaye, Alemu. And the article was included in Heteroatom Chemistry in 2021.Formula: C26H29ClN2O This article mentions the following:

Tandem conjugate addition-alkylation reaction of various amines with 伪-bromo-伪, 尾-unsaturated ketones resulted in near-quant. conversions into the corresponding aziridines when the reaction was carried out in the presence of 10 mol% of phase-transfer, PT catalysts in water. Some chiral quaternary ammonium salts derived from Cinchona alkaloids were investigated as water-stable PT catalysts. The scope and limitations of the reaction have also been investigated. The catalytic performances were significantly improved in comparison with the corresponding ordinary quaternary ammonium salt catalysts, and excellent yields (81%-96%) were obtained. Although an increase in the rate of aziridination has been accomplished, no stereoselectivity was observed The pos. values of the protocol have been confirmed. 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: 69221-14-3Formula: C26H29ClN2O).

(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 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. Processes involving the fragmentation of quinuclidines in chemical reactions and under electron impact and reactions involving expansion of the quinuclidine ring and intermediate cleavage of the bicyclic system are examined.聽 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).Formula: C26H29ClN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

New quinoline derivatives as nicotinic receptor modulators was written by Manetti, Dina;Bellucci, Cristina;Dei, Silvia;Teodori, Elisabetta;Varani, Katia;Spirova, Ekaterina;Kudryavtsev, Denis;Shelukhina, Irina;Tsetlin, Victor;Romanelli, Maria Novella. And the article was included in European Journal of Medicinal Chemistry in 2016.COA of Formula: C7H16Cl2N2 This article mentions the following:

As a continuation of previous work on quinoline derivatives, which showed some preference (2-3 times) for the 伪7 with respect to 伪4尾2 acetylcholine nicotinic receptors (nAChRs),the authors synthesized a series of novel azabicyclic or diazabicyclic compounds carrying a quinoline or isoquinoline ring, with the aim of searching for more selective 伪7 nAChR compounds Radioligand binding studies on 伪7* and 伪4尾2* nAChRs (rat brain homogenate) revealed one compound with a 2-fold higher affinity for the 伪4尾2*-subtype, and four compounds with at least 3-fold higher affinity for 伪7* nAChR. The most promising compound showed a K_i鈭?00 nM and over 10-fold selectivity for 伪7* nAChR. Other compounds at 50 渭M suppressed ion currents induced in the rat 伪4尾2 nAChR and the chimeric nAChR composed of the ligand-binding domain of the chick 伪7 and transmembrane domain of the 伪1 glycine receptor, expressed in Xenopus oocytes. Calcium imaging experiments on the human 伪7 nAChR expressed in the Neuro2a cells and potentiated by PNU-120596 confirmed the antagonistic activity for one compound and on the contrary other compounds were agonists with the EC₅₀ values in the range of 1.0-1.6 渭M. Thus, the introduced modifications allowed us to enhance the selectivity of quinolines towards 伪7 nAChR and to get novel compounds with agonistic activity. The synthesis of the target compounds was achieved by a reaction of 1,4-diazabicyclo[3.2.2]nonane, 1,4-diazabicyclo[3.2.1]octane dihydrochloride, 1-Azabicyclo[2.2.2]octan-3-amine, hydrochloride (1:2) with (bromo)quinoline derivatives, quinolinecarboxylic acid derivatives, isoquinolinecarboxylic acid derivatives The title compounds thus formed included . In the experiment, the researchers used many compounds, for example, 3-Aminoquinuclidine dihydrochloride (cas: 6530-09-2COA of Formula: C7H16Cl2N2).

3-Aminoquinuclidine dihydrochloride (cas: 6530-09-2) 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. 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: C7H16Cl2N2

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

New method and reagents in organic synthesis. 75. Asymmetric synthesis of 伪-hydroxy ketones using chiral phase transfer catalysts was written by Masui, Moriyasu;Ando, Akira;Shioiri, Takayuki. And the article was included in Tetrahedron Letters in 1988.HPLC of Formula: 69221-14-3 This article mentions the following:

Optically active 伪-hydroxy ketones are obtained by oxidation of achiral ketones with mol. O in a 2 phase system using chiral phase transfer catalysts. Thus, hydroxylation of tetralones I (R = H, R¹ = Me, Et) in the presence of cinchonine derivative II gave hydroxy derivatives (S)-I (R = OH, R¹ = Me, Et) in 95-98% yields and 70-72% enantiomeric excess. 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: 69221-14-3HPLC of Formula: 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 acts as a catalyst, a chemical building block and is used in organic synthesis. It is employed to prepare quinine and alkaloids. 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).HPLC of Formula: 69221-14-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider