Heterocyclic Building Blocks-Quinuclidine

Catalytic enantioselective Michael addition of 1-fluoro-bis(phenylsulfonyl)methane to α,β-unsaturated ketones catalyzed by cinchona alkaloids was written by Furukawa, Tatsuya;Shibata, Norio;Mizuta, Satoshi;Nakamura, Shuichi;Toru, Takeshi;Shiro, Motoo. And the article was included in Angewandte Chemie, International Edition in 2008.HPLC of Formula: 69221-14-3 This article mentions the following:

The ammonium salts of cinchona alkaloids possessing sterically demanding substituents effectively catalyzed the enantioselective 1,4-conjugate addition of 1-fluorobis(phenylsulfonyl)methane to α,β-unsaturated ketones to furnish the Michael adducts in high yield with excellent enantioselectivity. The adducts are useful for the synthesis of chiral monofluoromethylated mols. 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. 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.HPLC of Formula: 69221-14-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Organocatalytic regioselective Michael additions of cyclic enones via asymmetric phase transfer catalysis was written by Ceccarelli, Roberto;Insogna, Susanna;Bella, Marco. And the article was included in Organic & Biomolecular Chemistry in 2006.Reference of 69221-14-3 This article mentions the following:

Cyclohexanone and cycloheptanone can be enantioselectively functionalized in the 3-position with up to 92% ee and 87% ee, resp., by the base-promoted dimerization of the corresponding enones using 3,4,5-tri(benzyloxy)benzyl cinchoninium bromide as a new effective catalyst. The enantioselective addition of 2-cyclohexenone with tert-Bu cinnamyl ketone under similar conditions is also studied. 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. In alkane solvents quinuclidine is a Lewis base that forms adducts with a variety of Lewis acids. 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

A General Strategy for the Synthesis of Cyclic N-Aryl Hydroxamic Acids via Partial Nitro Group Reduction was written by McAllister, Laura A.;Bechle, Bruce M.;Dounay, Amy B.;Evrard, Edelweiss;Gan, Xinmin;Ghosh, Somraj;Kim, Ji-Young;Parikh, Vinod D.;Tuttle, Jamison B.;Verhoest, Patrick R.. And the article was included in Journal of Organic Chemistry in 2011.Computed Properties of C37H37BrN2O This article mentions the following:

We describe a generalized approach to stereocontrolled synthesis of substituted cyclic hydroxamic acids (3-amino-1-hydroxy-3,4-dihydroquinolinones), e.g. I (R = F₃CO, MeO, Me, Cl), by selective reduction of substituted 2-nitrophenylalanine substrates. Compounds in this series have antibacterial properties and have also recently been reported as KAT II inhibitors. The key nitrophenyl alanine intermediates are prepared enantioselectively in excellent yield by phase transfer catalyzed alkylation of the corresponding nitrobenzyl bromides. The scope and limitations of the reductive cyclization transformation have been explored with attention to the effects of substitution pattern and electronics on reaction efficiency and byproduct formation. In addition, a novel activated trifluoroethyl ester cyclization strategy has been developed as an alternate approach to the most sterically demanding systems in this series. 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. The development of synthetic approaches for efficient construction of novel quinuclidine derivatives is of great significance. 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.Computed Properties of C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Organocatalytic asymmetric [4+2] cyclization of 2-benzothiazolimines with azlactones: access to chiral benzothiazolopyrimidine derivatives was written by Ni, Qijian;Wang, Xuyang;Xu, Fangfang;Chen, Xiaoyun;Song, Xiaoxiao. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.Name: 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 organocatalytic asym. domino Mannich/cyclization reaction between 2-benzothiazolimines I (R = H, 6-OMe, 5-Br, etc.; R¹ = Ph, 4-MeC₆H₄, 2-thienyl, etc.) with azlactones II (R² = Me, Bn, 4-FC₆H₄CH₂, etc.; R³ = Ph, 4-MeC₆H₄, 1-naphthyl, etc.) has been successfully developed. With the bifunctional squaramide catalyst, this formal [4+2] cyclization occurs with good to high yields and excellent stereoselectivities (up to 99% ee, >20 : 1 dr), providing an efficient and mild access to chiral benzothiazolopyrimidines III (R = H, 6-OMe, 5-Br, etc.; R¹ = Ph, 4-MeC₆H₄, 2-thienyl, etc.; R² = Me, Bn, 4-FC₆H₄CH₂, etc.; R³ = Ph, 4-MeC₆H₄, 1-naphthyl, etc.) bearing adjacent tertiary and quaternary stereogenic centers. 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: 1256245-79-0Name: 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.Name: 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

Flexible total synthesis of biphenomycin B was written by Waldmann, Herbert;He, Yu-Peng;Tan, Hao;Arve, Lars;Arndt, Hans-Dieter. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2008.Formula: C37H37BrN2O This article mentions the following:

A total synthesis of the biaryl antibiotic biphenomycin B in 11 steps and 14% yield from benzyl bromide is reported. The key steps were a clean Suzuki-Miyaura coupling of a free acid iodide, a novel 4-hydroxyornithine synthesis, and a high-yielding macrolactamization. A practical deprotection protocol allowed isolation of the target compound with excellent recovery and purity. 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. 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.Formula: C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Cumyl Ester as the C-Terminal Protecting Group in the Enantioselective Alkylation of Glycine Benzophenone Imine was written by Respondek, Tomasz;Cueny, Eric;Kodanko, Jeremy J.. And the article was included in Organic Letters in 2012.Product Details of 200132-54-3 This article mentions the following:

Cumyl ester is an optimal C-terminal protecting group for glycine benzophenone imine in asym. alkylation reactions catalyzed by Cinchona chiral phase-transfer catalysts. High levels of enantioselectivity have been obtained (up to 94% ee) with this substrate, which provides an attractive alternative to the analogous tert-Bu ester. N-terminal imines and the C-terminal esters can be cleaved from alkylation products by hydrogenolysis, while maintaining acid-labile side chain protecting groups. 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. 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.Product Details of 200132-54-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Organocatalytic Enantioselective Synthesis of Tetrahydrofluoren-9-ones via Vinylogous Michael Addition/Henry Reaction Cascade of 1,3-Indandione-Derived Pronucleophiles was written by Mohlmann, Lennart;Chang, Geng-Hua;Madhusudhan Reddy, G.;Lee, Chia-Jui;Lin, Wenwei. And the article was included in Organic Letters in 2016.SDS of cas: 1256245-79-0 This article mentions the following:

An unprecedented organocatalytic enantioselective vinylogous Michael addition and Henry cyclization cascade is presented for the synthesis of highly substituted tetrahydrofluoren-9-ones employing novel 1,3-indandione-derived pronucleophiles and nitroalkenes. Following a very simple protocol, a wide range of products were obtained in good to excellent yields and with excellent enantioinduction (43-98% yields, up to 98% ee). The reaction proceeded with excellent diastereocontrol despite the simultaneous generation of four stereogenic centers. Surprisingly, when 2-(1-phenylethylidene)-1H-indandione was used as a pronucleophile, no cyclization was observed, and only Michael addition adducts were furnished in very good yields and excellent enantioselectivities. 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: 1256245-79-0SDS of cas: 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 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.SDS of cas: 1256245-79-0

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Synthesis of (+)-N-benzylcinchoninium chloride under microwave irradiation and its application in the resolution of racemic BINOL was written by Ding, Ying-hong;Liang, Xiang;Zhang, Guang-wen;Chen, Ya-xing. And the article was included in Huaxue Shiji in 2004.Category: quinuclidine This article mentions the following:

The mixture of benzyl chloride and cinchonine was heated at 100-104° in DMF for about 15 min under microwave irradiation to give (+)-N-benzylcinchoninium chloride in 55.1% yield, the efficient resolution of racemic BINOL has been achieved with (+)-N-benzylcinchoninium chloride. 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: 69221-14-3Category: quinuclidine).

(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. 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%–96%), diastereoselectivity (up to >20/1 dr), and enantioselectivity (up to >99% ee).Category: quinuclidine

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Regiodivergent Vinylogous-Cyclization Reactions of Cyclic α-Amide Enone Acceptors: Synthesis of Highly Enantioenriched Heterobicyclic Structures was written by Zhang, Yili;Lu, Xue;Wang, Yichen;Xu, Hui;Zhan, Ruoting;Chen, Weiwen;Huang, Huicai. And the article was included in Organic Letters in 2019.Related Products of 1256245-79-0 This article mentions the following:

A vinylogous addition-cyclization reaction of cyclic α-amide enones with good yields and excellent regioselectivity catalyzed by cinchona squaramides has been reported. Using 4-aryl-3-butenyl N-acylpyrazoles as nucleophiles led to 1,4-selective γ-addition of enones, and 1,2-selective γ-addition of enones took place when 3-aryl-3-butenyl N-acylpyrazoles was used as the donors. The 1,4- and 1,2-selective γ-adducts are then formed into the corresponding highly stereoselective and enantioselective fused bicyclic and spirocyclic products by intramol. cyclization. The synthetic utility of the products has also been demonstrated through further transformations of the products. 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: 1256245-79-0Related Products 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. 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%–96%), diastereoselectivity (up to >20/1 dr), and enantioselectivity (up to >99% ee).Related Products of 1256245-79-0

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider