Tag: 420.9743

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

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

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

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

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

Designing Fluorinated Cinchona Alkaloids for Enantioselective Catalysis: Controlling Internal Rotation by a Fluorine-Ammonium Ion gauche Effect (φ_NCCF) was written by Tanzer, Eva-Maria;Schweizer, W. Bernd;Ebert, Marc-Olivier;Gilmour, Ryan. And the article was included in Chemistry – A European Journal 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:

The C9 position of cinchona alkaloids functions as a mol. hinge, with internal rotations around the C8-C9 (τ₁) and C9-C4′ (τ₂) bonds giving rise to four low energy conformers (1; anti-closed, anti-open, syn-closed, and syn-open). By substituting the C9 carbinol center by a configurationally defined fluorine substituent, a fluorine-ammonium ion gauche effect (σ_C-H→σ_C-F*; F^δ-···N⁺) encodes for two out of the four possible conformers (2). This constitutes a partial solution to the long-standing problem of governing internal rotations in cinchonium-based catalysts relying solely on a fluorine conformational effect. 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. 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.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

A new enantioselective synthesis of N-arylaziridines by phase-transfer catalysis was written by Aires-de-Sousa, Joao;Lobo, Ana M.;Prabhakar, Sundaresan. And the article was included in Tetrahedron Letters in 1996.Name: (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride This article mentions the following:

Chiral N-arylaziridines I (R² = CO₂CMe₃, SOPh, X = H, 4-Me, 4-Br, 3-Me, 3-Br, 4-NO₂) are obtained from N-acyl-N-arylhydroxylamines II and H₂C:CHR² using quaternary salts of Cinchona alkaloids as phase-transfer catalysts. 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: 69221-14-3Name: (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 acts as a catalyst, a chemical building block and is used in organic synthesis. 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.Name: (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride

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

Asymmetric C-alkylation with chiral phase-transfer catalysis. Synthesis of optically active derivatives of 2-indolinone was written by Chen, Banghua;Ji, Qinge. And the article was included in Huaxue Xuebao in 1989.Formula: C26H29ClN2O This article mentions the following:

By using different chiral quaternary ammonium salts as phase-transfer catalysts, the asym. C-alkylation of 1,3-dimethyl-5-methoxy-2-indolinone with various alkyl bromides is carried out. The effects of the catalysts, alkylating agents, solvents, and reaction temperatures on the optical activity of the products are 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: 69221-14-3Formula: 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 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).Formula: C26H29ClN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Cation-induced chirality in a bifunctional metal-organic framework for quantitative enantioselective recognition was written by Han, Zongsu;Wang, Kunyu;Guo, Yifan;Chen, Wenjie;Zhang, Jiale;Zhang, Xinran;Siligardi, Giuliano;Yang, Sihai;Zhou, Zhen;Sun, Pingchuan;Shi, Wei;Cheng, Peng. And the article was included in Nature Communications in 2019.Recommanded Product: 69221-14-3 This article mentions the following:

The integration of luminescence and chirality in easy-scalable metal-organic frameworks gives rise to the development of advanced luminescent sensors. To date, the synthesis of chiral metal-organic frameworks is poorly predictable and their chirality primarily originates from components that constitute the frameworks. By contrast, the introduction of chirality into the pores of metal-organic frameworks has not been explored to the best of our knowledge. Here, we demonstrate that chirality can be introduced into an anionic Zn-based metal-organic framework via simple cation exchange, yielding dual luminescent centers comprised of the ligand and Tb³⁺ ions, accompanied by a chiral center in the pores. This bifunctional material shows enantioselectivity luminescent sensing for a mixture of stereoisomers, demonstrated for Cinchonine and Cinchonidine epimers and amino alc. enantiomers, from which the quant. determination of the stereoisomeric excess has been obtained. This study paves a pathway for the design of multifunctional metal-organic framework systems as a useful method for rapid sensing of chiral 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: 69221-14-3Recommanded Product: 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. 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.Recommanded Product: 69221-14-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider