Heterocyclic Building Blocks-Quinuclidine

A Ruthenium(II) Tris(bipyridyl) Amino Acid: Synthesis and Direct Incorporation into an α-Helical Peptide by Solid-Phase Synthesis was written by Kise, Kenneth J. Jr.;Bowler, Bruce E.. And the article was included in Inorganic Chemistry in 2002.Safety of (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide This article mentions the following:

The synthesis of a ruthenium(II) tris(bipyridyl) amino acid is described along with its incorporation into a helix-forming peptide using standard solid-phase peptide synthesis methods. The phys. properties of the metalloamino acid sep. and in the context of the peptide are reported. The electrochem. potential, absorption spectrum, emission and excitation spectra, and emission lifetime data for the ruthenium(II) tris(bipyridyl) amino acid are similar to those of ruthenium(II) tris(bipyridine), indicating that the amino acid functionality introduced on one of the bipyridine rings does not strongly perturb the properties of the metal complex. The ruthenium(II) tris(bipyridyl) amino acid is amenable to direct incorporation into a synthetic peptide using solid-phase methods and BOC/benzyl chem. The 22 amino acid alanine-based peptide produced is 67% helical at 0° in aqueous buffer, as measured by CD spectroscopy. The 2,2,2-trifluoroethanol helix induction curve and the temperature dependence of the helicity are typical for alanine-based peptides. The Lifson-Roig helix propagation parameter, w, derived from CD and NMR-monitored kinetic hydrogen-deuterium exchange is 0.5 ± 0.1 at 0°, indicating a moderate helix propensity for this metalloamino acid. 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: 200132-54-3Safety of (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide).

(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 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.  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.Safety of (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Enantioselective [3+2] annulation of 4-isothiocyanato pyrazolones and alkynyl ketones under organocatalysis was written by Wang, Wenyao;Wei, Shiqiang;Bao, Xiaoze;Nawaz, Shah;Qu, Jingping;Wang, Baomin. And the article was included in Organic & Biomolecular Chemistry in 2021.SDS of cas: 1256245-79-0 This article mentions the following:

An asym. [3+2] annulation reaction of 4-isothiocyanato pyrazolones with alkynyl ketones in the presence of an organic catalyst derived from a cinchona alkaloid under mild conditions was realized. This protocol provided unprecedented expeditious accessed to a wide range of optically active spiro[pyrroline-pyrazolones] with various electronic properties in high yields with good to 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. 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).SDS of cas: 1256245-79-0

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Solid-liquid phase transfer catalysis without solvent: an improvement for chiral Michael addition of N-acetylaminomalonate to chalcone was written by Loupy, Andre;Sansoulet, Jean;Zaparucha, Anne;Merienne, Claude. And the article was included in Tetrahedron Letters in 1989.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:

The reaction of chalcone with AcNHCH(CO₂Et)₂ to give PhCOCH₂CHPhC(CO₂Et)₂NHAc in the absence of solvent was catalyzed by PhCH(OH)CHMeN⁺R¹Me₂ X^– (R¹ = alkyl, PhCH₂, substituted benzyl; X = Br, Cl). Also used were cinchonines I (R¹ = H, NO₂; R² = OMe, H; X = Cl, Br). 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.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.  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

Efficient unified synthesis of diverse bridged polycyclic scaffolds using a complexity-generating ‘stitching’ annulation approach was written by Rice, Scott;Cox, Daniel J.;Marsden, Stephen P.;Nelson, Adam. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2021.Computed Properties of C7H16Cl2N2 This article mentions the following:

Regioselective and stereospecific directed C-H arylation of simple amine substrates e.g., exo-2-aminonorbornane, and cyclisation, delivered three-dimensional scaffolds e.g., (1R,3aR,4R,10bS)-2,3,3a,4,5,10b-hexahydro-1,4-methanobenzo[c]cyclopenta[e]azepin-6(1H)-one. The unified approach significantly expanded the range of bridged ring systems that contain both a nitrogen atom and an aromatic ring. In the experiment, the researchers used many compounds, for example, 3-Aminoquinuclidine dihydrochloride (cas: 6530-09-2Computed Properties 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. 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).Computed Properties of C7H16Cl2N2

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Organocatalytic Cascade Sulfa-Michael/Aldol Reaction of β,β-Disubstituted Enones: Enantioselective Synthesis of Tetrahydrothiophenes with a Trifluoromethylated Quaternary Center was written by Su, Yu;Ling, Jun-Bing;Zhang, Shuang;Xu, Peng-Fei. And the article was included in Journal of Organic Chemistry in 2013.Application of 1256245-79-0 This article mentions the following:

A bifunctional squaramide-catalyzed sulfa-Michael/aldol cascade reaction initiated by sulfa-Michael addition of mercaptoacetaldehyde to β-aryl-β-trifluoromethylated enones is successfully developed. The functionalized tetrahydrothiophenes with three continuous stereocenters including a trifluoromethylated quaternary carbon are readily obtained with moderate to good yields and high enantioselectivities. Thus, e.g., cascade reaction of mercaptoacetaldehyde (generated in situ from is dimer 1,4-dithiane-2,5-diol) with enone (E)-PhCOCH:C(Ph)(CF₃) in presence of cinchona alkaloid-derived bifunctional squaramide afforded tetrahydrothiophene I (85% yield, dr 4:1 ee 84%). 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: 1256245-79-0Application 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. It is employed to prepare quinine and alkaloids. Quinuclidine is an organic compound and a bicyclic amine and used as a catalyst and a chemical building block. It is a strong base with pKa of the conjugate acid of 19.5. It can be prepared by reduction of quinuclidone.Application of 1256245-79-0

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Cinchona-derived quaternary ammonium salts-improved asymmetric cycloaddition of CO₂ to epoxides was written by Zhang, Suling;Song, Yingying;Jing, Huanwang;Yan, Peng;Cai, Qiang. And the article was included in Cuihua Xuebao in 2009.Application of 69221-14-3 This article mentions the following:

A new catalyst system, salenCoX/cinchona-derived quaternary ammonium compound, was developed to catalyze a cycloaddition of CO₂ to epoxides under extremely mild reaction conditions. Chiral propylene carbonate was obtained with good enantioselectivity in the presence of the above-mentioned catalyst. The anions of the catalysts and the co-catalysts evidently affect the activity and enantioselectivity of the reaction. The activity of (S,S)-catalysts in terms of anions was confirmed to be in the order 2-nitrophenoxy > 2,4,6-trinitrophenoxy > NO₃^–> OAc^–> CF₃CO₂^– ≈ Br^–> Cl^–> OTs^–. A cocatalyst with a Cl^– anion gives the highest ee value for propylene carbonate. In contrast, a cocatalyst with a bromide (Br^–) anion has higher activity. The highest enantiomeric excess observed for the enantioselective preparation of propylene carbonate was 73%. 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 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. 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 of 69221-14-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Organocatalytic asymmetric cascade Michael/hemiketalization/retro-aldol reaction of 3-acetyl-oxindole with β,γ-unsaturated ketoesters catalyzed by bifunctional amino-squaramides was written by Zhou, Jing;Jia, Li-Na;Wang, Qi-Lin;Peng, Lin;Tian, Fang;Xu, Xiao-Ying;Wang, Li-Xin. And the article was included in Tetrahedron in 2014.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:

α-Ketoesters R¹CH:CHCOCO₂R² undergo an unprecedented organocatalytic asym. Michael/Hemiketalization/retro-aldol cascade sequence with 1-R³-3-(COR⁴)-2-indolones, yielding products I (R¹ = aryl, 2-thienyl, ⁱPr; R² = Me, Et, ⁱPr; R³ = H, Et, ⁱPr, PhCH₂, Me; R⁴ = Me, Et, Ph) catalyzed by bifunctional amino-squaramides and thioureas I (R = H, OMe; X = CS, 3,4-dioxo-1-cyclobuten-1,2-diyl) is described. The corresponding adducts I were generally obtained in high yields (up to 97%) with moderate diastereo- (up to 79:21 dr) and good enantioselectivities (up to 90% ee). 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.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.  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.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

Stereoselective Organo-catalyzed Synthesis of α-Fluorinated β-Amino Thioesters and Their Application in Peptide Synthesis was written by Cosimi, Elena;Engl, Oliver D.;Saadi, Jakub;Ebert, Marc-Olivier;Wennemers, Helma. And the article was included in Angewandte Chemie, International Edition in 2016.SDS of cas: 1256245-79-0 This article mentions the following:

α-Fluorinated β-amino thioesters were obtained in high yields and stereoselectivities by organo-catalyzed addition reactions of α-fluorinated mono-thiomalonates to N-Cbz- and N-Boc-protected imines. The transformation requires catalyst loadings of only 1 mol % and proceeds under mild reaction conditions. The obtained addition products were readily used for coupling-reagent-free peptide synthesis in solution and on solid phase. The α-fluoro-β-(carb)amido moiety showed distinct conformational preferences, as determined by crystal structure and NMR spectroscopic anal. 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. 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.SDS of cas: 1256245-79-0

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

An efficient homogeneous catalytic enantioselective synthesis of α-amino acid derivatives was written by O’Donnell, Martin J.;Delgado, Francisca;Hostettler, Curt;Schwesinger, Reinhard. And the article was included in Tetrahedron Letters in 1998.Name: (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide This article mentions the following:

The catalytic enantioselective alkylation of glycinate imine Ph₂C:NCH₂CO₂CMe₃ is realized by an efficient homogeneous reaction with alkyl halides, the neutral, non-ionic phosphazene bases I (BEMP) or II (BTPP), and chiral quaternary ammonium salts derived from cinchona alkaloids. 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: 200132-54-3Name: (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide).

(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. 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).Name: (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Synthesis of 6-fluoro-L-Dopa was written by Zhang, Lan;Tang, Ganghua;Yin, Duanzhi;Tang, Xiaolan;Wang, Yongxian. And the article was included in Zhongguo Yaowu Huaxue Zazhi in 2001.Computed Properties of C37H37BrN2O This article mentions the following:

Title compound, an important positron-emission tomog. (PET) tracer, was synthesized from 4-amino-1,2-dimethoxybenzene via phase transfer catalysis nucleophilic substitution, in nine steps, giving the product with satisfied yield. . 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. Quinuclidine is an organic compound and a bicyclic amine and used as a catalyst and a chemical building block. It is a strong base with pKa of the conjugate acid of 19.5. It can be prepared by reduction of quinuclidone.Computed Properties of C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider