Day: February 22, 2023

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

Catalytic asymmetric cycloetherification via intramolecular oxy-Michael addition of enols was written by Murata, Ryuichi;Asano, Keisuke;Matsubara, Seijiro. And the article was included in Tetrahedron in 2021.Reference of 1256245-79-0 This article mentions the following:

In this study, the asym. cycloetherification of enols were presented, which were generated in situ from enone-bearing ketones, using chiral bifunctional organocatalysts bearing amino and squaramide groups. This transformation chemo- and enantioselectively afforded dihydropyran derivatives I [R¹ = Ph, 4-BrC₆H₄, 2-naphthyl, etc.; R² = CF₃, CF₂Br, CO₂Et, Ph; R³ = H, C(O)Ph], which were the core structures of building blocks for synthesizing glycans. 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.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).Reference of 1256245-79-0

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Stereoselective synthesis of epoxyisoprostanes: an organocatalytic and “pot-economy” approach was written by Weng, Jiang;Wang, Sheng;Huang, Lin-Jie;Luo, Zhang-Yi;Lu, Gui. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2015.Electric Literature of C26H29ClN2O This article mentions the following:

An efficient and direct synthetic route to epoxyisoprostane EC Me ester (I) has been accomplished in 8 steps (10% overall yield) from readily available starting materials using a series of asym. organocatalytic reactions and one-pot operations. 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: 69221-14-3Electric Literature of 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. 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.Electric Literature of C26H29ClN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Polymeric pseudo-liquid membranes from poly(octadecyl methacrylate) was written by Tsujimoto, Hiroki;Yoshikawa, Masakazu. And the article was included in Journal of Membrane Science in 2013.SDS of cas: 200132-54-3 This article mentions the following:

The novel liquid membrane system, which is named polymeric pseudo-liquid membrane, was constructed from poly(octadecyl methacrylate) (PC18MA), which showed a rubbery state under operating conditions, as a membrane matrix, and dibenzo-18-crown-6 (DB18C6) for the transport of KCl or O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide (AAMC) for that of racemic mixture of phenylglycine (Phegly) as a carrier. The results of KCl transport revealed that KCl transport was attained by carrier-diffusion mechanism even though membrane matrix was composed of polymeric material. The polymeric pseudo-liquid membrane containing chiral carrier AAMC showed optical resolution ability, in other words, the membrane selectively transported L-Phegly and its permselectivity toward L-Phegly reached 1.48 at the operating temperature of 40 掳C. Chiral separation ability was greatly dependent on the operating temperature and a wide range of permselectivity from L-isomer to D-isomer permselectivity was attained by adjusting the operating temperature The present study revealed that the polymeric pseudo-liquid membrane is a promising membrane system in membrane 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: 200132-54-3SDS of cas: 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. It is employed to prepare quinine and alkaloids. 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.SDS of cas: 200132-54-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Enantioselective Synthesis of Benzofuran-Fused N-Heterocycles via Chiral Squaramide Catalyzed [4 + 2] Cyclization of Azadienes with Azlactones was written by Li, Xiaoping;Yan, Juzhang;Qin, Jialiang;Lin, Shilin;Chen, Weiwen;Zhan, Ruoting;Huang, Huicai. And the article was included in Journal of Organic Chemistry in 2019.Quality Control of 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 This article mentions the following:

An asym. cyclization reaction of azadienes and azlactones was investigated by employing a Cinchona squaramide catalyst, which could afford a series of benzofuran-fused six-membered heterocycles containing a 伪,伪-disubstituted amino acid unit in a highly diastereoselective (>20:1 dr) and enantioselective (up to 99% ee) manner with good to excellent yields (up to 92%). A plausible pathway was proposed to explain the reaction process. 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: 1256245-79-0Quality Control of 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).

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. 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.Quality Control of 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

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Nucleophilic enantioselective synthesis of 6-fluoro-L-dopa via chiral catalytic phase-transfer alkylation was written by Tang, Ganghua;Tang, Xiaolan;Zhang, Lan;Wang, Yongxian. And the article was included in Zhongguo Yaowu Huaxue Zazhi in 2002.Formula: C37H37BrN2O This article mentions the following:

6-Fluoro-L-dopa was synthesized from 6-nitropiperonal via nucleophilic fluorination, reductive iodination, chiral catalytic phase-transfer alkylation, and hydrolysis reactions. The enantiomeric purity of 6-fluoro-L-dopa was determined by HPLC method using a chiral mobile phase and reversed-phase C₁₈ column. The overall yield from 6-nitropiperonal was 38%, and enantiomeric purity of 6-fluoro-L-dopa was above 95%. 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 is found as a structural component of some biomolecules including quinine. 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.Formula: C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Organocatalytic Regio- and Asymmetric C-Selective S_NAr Reactions-Stereoselective Synthesis of Optically Active Spiro-pyrrolidone-3,3′-oxoindoles was written by Bella, Marco;Kobbelgaard, Sara;Jorgensen, Karl Anker. And the article was included in Journal of the American Chemical Society in 2005.Product Details of 200132-54-3 This article mentions the following:

The first example of catalytic enantioselective nucleophilic aromatic substitution of 尾-dicarbonyl compounds is presented. An O-benzoylated cinchona alkaloid derivative catalyst gave a selective C-arylation reaction compared to, e.g., the corresponding benzylated catalyst which provided a 1:1 mixture of the C- and O-arylation products. The reaction proceeds well for various aromatic compounds with different 1,3-dicarbonyl compounds, and the optically active products are obtained in very high yields and with up to 92% ee. One further scope of this reaction is demonstrated by the synthesis of the optically active spiro-pyrrolidone-3,3′-oxoindole structure. 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. Quinuclidine is found as a structural component of some biomolecules including quinine. 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.Product Details of 200132-54-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider