Heterocyclic Building Blocks-Quinuclidine

Catalytic enantioselective cascade Michael/cyclization reaction of 3-isothiocyanato oxindoles with exocyclic α,β-unsaturated ketones en route to 3,2′-pyrrolidinyl bispirooxindoles was written by Kayal, Satavisha;Mukherjee, Santanu. And the article was included in Organic & Biomolecular Chemistry in 2016.Product Details of 1256245-79-0 This article mentions the following:

Cascade Michael/cyclization reactions between 3-isothiocyanato oxindoles and exocyclic α,β-unsaturated ketones are shown to proceed efficiently in the presence of a quinine-derived tertiary amino-squaramide catalyst and furnish 3,2′-pyrrolidinyl bispirooxindoles containing two spiro-quaternary and three contiguous stereocenters, e.g., I as a single diastereomer with excellent enantioselectivities (up to 99 : 1 er). 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. 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 1256245-79-0

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Perfectly green organocatalysis. Quaternary ammonium base triggered cyanosilylation of aldehydes was written by Wen, Yeqian;Liang, Mengwei;Wang, Yiming;Ren, Weimin;Lue, Xiaobing. And the article was included in Chinese Journal of Chemistry in 2012.Quality Control of (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride This article mentions the following:

Quaternary ammonium bases, such as aqueous Me₄NOH or Bu₄NOH, were an extraordinarily efficient catalyst for cyanosilylation of aldehydes. The addition reaction of trimethylsilyl cyanide to equivalent aldehydes could proceed smoothly with turnover frequency (TOF) up to 3000000 h^-1 and in near 100% yield under solvent-free conditions. These organic catalysts also tolerated various aldehydes including aromatic, aliphatic and α,β-unsaturated aldehydes. This process perfectly conforms to the features of green chem.: no waste regarding side-products and unconverted reactants, solvent-free, excellent catalytic activity, and no requirement for separation 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: 69221-14-3Quality Control 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 exists in a number of naturally occurring compounds, biologically active agents, and privileged catalysts and ligands for asymmetric catalysis. 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.Quality Control of (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Synthetic studies towards (-)-lemonomycin, synthesis of fused tetracycles was written by Couturier, Cedric;Schlama, Thierry;Zhu, Jieping. And the article was included in Synlett in 2006.Category: quinuclidine This article mentions the following:

The asym. synthesis of 1,3-lactol-bridged tetrahydroisoquinolines I [R = SiMe₂CMe₃, CH₂Ph; R¹ = CH₂CH(CO₂Me)₂; R² = CO₂CH₂Ph] was developed. Subsequent cyclizations of I (R = SiMe₂CMe₃, CH₂Ph) under acidic conditions lead to the formation of a tricyclic enamides II [R = SiMe₂CMe₃, CH₂Ph; R¹ = CH₂CH(CO₂Me)₂; R² = CO₂CH₂Ph]. II [R = CH₂Ph, R¹ = CH₂CH(CO₂Me)₂, R² = CO₂CH₂Ph] was in turn converted to a tetracyclic compound III. 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: 200132-54-3Category: quinuclidine).

(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.Category: quinuclidine

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

The cinchona alkaloid squaramide catalyzed asymmetric Pictet-Spengler reaction and related theoretical studies was written by Qi, Liang;Hou, Huacui;Ling, Fei;Zhong, Weihui. And the article was included in Organic & Biomolecular Chemistry in 2018.HPLC of Formula: 1256245-79-0 This article mentions the following:

The asym. Pictet-Spengler reaction between tryptamine derivatives and aldehydes has been developed with a cinchona alkaloid squaramide as the catalyst, affording the corresponding tetrahedron-β-carbolines in good to excellent yields and ee values. A rational mechanistic pathway has also been proposed based on DFT calculations 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: 1256245-79-0HPLC of Formula: 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. It is employed to prepare quinine and alkaloids. 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.HPLC of Formula: 1256245-79-0

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Divergent Asymmetric Reactions of ortho-Quinone Methides with α-Thiocyanato Indanones for the Synthesis of Spiro- and Fused-Indanones was written by Liu, Xianghui;Wang, Kai;Liu, Yan;Li, Can. And the article was included in Chemistry – A European Journal in 2021.COA of Formula: C32H28F6N4O3 This article mentions the following:

Reported in this work is a water triggered chemo-divergent enantioselective spiro-annulation and cascade reaction of ortho-quinone methides (o-QMs) with α-thiocyanato indanones catalyzed by a chiral organic base. In the case of spiro-annulation, the use of trace amount of water as additive is critical to achieve high enantioselectivity (up to 96% ee). We found that a cascade reaction was enabled by just tuning the ratio of water in solvent. Accordingly, two new highly efficient asym. reactions for the divergent synthesis of spiro- and fused-indanone scaffolds, i.e., I and II, with excellent enantioselectivities (up to 99% ee) were developed. Mechanistic investigations suggest that interfacial hydrogen bonding may play an important role in achieving the switchable reaction pathways. 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: 1256245-79-0COA of Formula: C32H28F6N4O3).

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 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.COA of Formula: C32H28F6N4O3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Thiol-ene Click Reaction as a General Route to Functional Trialkoxysilanes for Surface Coating Applications was written by Tucker-Schwartz, Alexander K.;Farrell, Richard A.;Garrell, Robin L.. And the article was included in Journal of the American Chemical Society in 2011.Electric Literature of C7H16Cl2N2 This article mentions the following:

Functionalized trialkoxysilanes are widely used to modify the surface properties of materials and devices. It will be shown that the photoinitiated radical-based thiol-ene “click” reaction provides a simple and efficient route to diverse trialkoxysilanes. A total of 15 trialkoxysilanes were synthesized by reacting either alkenes with 3-mercaptopropyltrialkoxysilane or thiols with allyltrialkoxysilanes in the presence of a photoinitiator. The functionalized trialkoxysilanes were obtained in quant. to near-quant. yields with high purity. The photochem. reactions can be run neat in standard borosilicate glassware using a low power 15 W blacklight. A wide range of functional groups is tolerated in this approach, and even complex alkenes click with the silane precursors. To demonstrate that these silanes can be used as surface coating agents, several were reacted with iron oxide superparamagnetic nanoparticles and the loadings quantified. The photoinitiated thiol-ene reaction thus offers a facile and efficient method for preparing surface-active functional trialkoxysilanes. In the experiment, the researchers used many compounds, for example, 3-Aminoquinuclidine dihydrochloride (cas: 6530-09-2Electric Literature of C7H16Cl2N2).

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

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Asymmetric induction in the synthesis of α-amino acid under phase transfer catalysis conditions was written by Jin, Chunxue;Xiong, Lizeng;Chen, Zikang;Yu, Lingchong. And the article was included in Beijing Shifan Daxue Xuebao, Ziran Kexueban in 1993.Computed Properties of C26H29ClN2O This article mentions the following:

Gabriel reaction of potassium phthalimide and (-)-menthyl α-bromocarboxylates are studied under solid-liquid chiral and nonchiral phase transfer catalysis conditions. Four optically active 2-phthalimido esters are synthesized under varied phase transfer catalysis conditions. Four L-predominant α-amino acids with optical yields 3% ∼ 13.5% are obtained by hydrazinolysis and hydrolysis of these N-substituted phthalimides. 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: 69221-14-3Computed Properties 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 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.Computed Properties of C26H29ClN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Catalytic Atropenantioselective Heteroannulation between Isocyanoacetates and Alkynyl Ketones: Synthesis of Enantioenriched Axially Chiral 3-Arylpyrroles was written by Zheng, Sheng-Cai;Wang, Qian;Zhu, Jieping. And the article was included in Angewandte Chemie, International Edition in 2019.Application In Synthesis of 2-(Diphenylphosphino)-N-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)benzamide This article mentions the following:

In the presence of Ag₂O and a quinine- or quinidine-derived phosphine, arylethynyl aryl ketones such as I (R = Ph, 4-BrC₆H₄, 4-ClC₆H₄, 4-MeOC₆H₄, 4-MeC₆H₄, 4-t-BuC₆H₄, 3-MeOC₆H₄; R¹ = Me, Et, i-Pr, Ac) underwent enantioselective cycloaddition reactions with isocyanoacetates such as Et isocyanoacetate to yield (aryl)aroylpyrrolecarboxylates such as II (R = Ph, 4-BrC₆H₄, 4-ClC₆H₄, 4-MeOC₆H₄, 4-MeC₆H₄, 4-t-BuC₆H₄, 3-MeOC₆H₄; R¹ = Me, Et, i-Pr, Ac) in 46-98% yields and in 82-96% ee. In the experiment, the researchers used many compounds, for example, 2-(Diphenylphosphino)-N-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)benzamide (cas: 1630973-03-3Application In Synthesis of 2-(Diphenylphosphino)-N-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)benzamide).

2-(Diphenylphosphino)-N-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)benzamide (cas: 1630973-03-3) belongs to quinuclidine derivatives. Quinuclidine is found as a structural component of some biomolecules including quinine. 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.Application In Synthesis of 2-(Diphenylphosphino)-N-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)benzamide

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Asymmetric Catalysis Using Modularly Designed Organocatalysts: Synthesis of Fused Tricyclic Pyrano[3′,2′:5,6]pyrano[2,3-c]pyrrole Derivatives was written by Lu, Xue;Zhang, Yili;Wang, Yichen;Chen, Yuzhen;Chen, Weiwen;Zhan, Ruoting;Zhao, John C.-G.;Huang, Huicai. And the article was included in Advanced Synthesis & Catalysis in 2019.Category: quinuclidine This article mentions the following:

A highly enantioselective organocatalytic Michael addition-acetalation/oxa-Michael reaction involving aldehydes and dioxopyrrolidines has been discovered. The asym. reaction is mediated by modularly designed organocatalysts (MDOs) self-assembled from cinchona alkaloid derivatives and amino acids providing a range of optically active tricyclic hexahydro-2H-pyrano[3′,2′:5,6]pyrano[2,3-c]pyrrole derivatives in high yields (up to 99%) with good to excellent enantioselectivities (up to 99% ee) under mild reaction conditions. 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: 1256245-79-0Category: quinuclidine).

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 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.Category: quinuclidine

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Hydrolytic enantioselective protonation of cyclic dienyl esters and a β-diketone with chiral phase-transfer catalysts was written by Yamamoto, Eiji;Gokuden, Daichi;Nagai, Ayano;Kamachi, Takashi;Yoshizawa, Kazunari;Hamasaki, Akiyuki;Ishida, Tamao;Tokunaga, Makoto. And the article was included in Organic Letters in 2012.Product Details of 69221-14-3 This article mentions the following:

Hydrolytic enantioselective protonation of dienyl esters and a β-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active α,β-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er). 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: 69221-14-3Product Details 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 acts as a catalyst, a chemical building block and is used in organic synthesis. It is employed to prepare quinine and alkaloids. 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 69221-14-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider