Heterocyclic Building Blocks-Quinuclidine

A short enantioselective synthesis of protected L-3-hydroxy-4-methoxy-5-methyl phenylalanine and its corresponding aldehyde – a common subunit of ecteinascidin-743, safracin and congeners was written by De Paolis, Michael;Chen, Xiaochuan;Zhu, Jieping. And the article was included in Synlett in 2004.Electric Literature of C37H37BrN2O This article mentions the following:

An asym. synthesis of appropriately protected L-3-hydroxy-4-methoxy-5-Me phenylalanine from 3-methylcatechol is described featuring a key enantioselective alkylation step. 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: 200132-54-3Electric Literature 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 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.Electric Literature of C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Total Synthesis of Aurofusarin: Studies on the Atropisomeric Stability of Bis-Naphthoquinones was written by Qi, Chao;Wang, Wenyu;Reichl, Kyle D.;McNeely, James;Porco, John A. Jr.. And the article was included in Angewandte Chemie, International Edition in 2018.Recommanded Product: 200132-54-3 This article mentions the following:

An efficient annulation involving pyrone addition to a quinone and Dieckmann condensation was developed for rapid assembly of a γ-naphthopyrone monomeric precursor to the bis-naphthoquinone natural product aurofusarin. Dimerization was achieved through Pd(II)-catalyzed dehydrogenative coupling. Further studies employing asym. nucleophilic epoxidation indicate that the atropisomers of aurofusarin and derivatives are not configurationally stable at ambient temperature 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: 200132-54-3Recommanded Product: 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. 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.Recommanded Product: 200132-54-3

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

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

Quantum Mechanical Transition-State Analysis Reveals the Precise Origin of Stereoselectivity in Chiral Quaternary Cinchonidinium Phase-Transfer Catalyzed Enolate Allylation was written by Cook, Thomas C.;Andrus, Merritt B.;Ess, Daniel H.. And the article was included in Organic Letters in 2012.Recommanded Product: (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:

D. functional theory was used to model glycinate enolate binding and enantiomeric allylation transition states mediated by the cinchonidinium phase-transfer catalyst 2. Transition states show oxy-anion-ammonium interactions in contrast to π-face interactions in the ground states. The details of stereoselectivity are described within the quaternary ammonium-tetrahedron face model. 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: 200132-54-3Recommanded Product: (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. Quinuclidine is found as a structural component of some biomolecules including quinine. 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.Recommanded Product: (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

Synthetic studies on bioactive natural polyketides: intramolecular nitrile oxide-olefin cycloaddition approach for construction of a macrolactone skeleton of macrosphelide B was written by Paek, Seung-Mann;Suh, Young-Ger. And the article was included in Molecules in 2011.Product Details of 200132-54-3 This article mentions the following:

Studies on the synthesis of macrosphelide B (I) via an intramol. nitrile oxide-olefin cycloaddition (INOC) was described. In particular, an asym. INOC approach using phase transfer catalysts seemed to be a potentially efficient and versatile procedure for the construction of the macrolactone skeleton of macrosphelide B in terms of facial selectivity. This preliminary and unprecedented stereoselective procedure is anticipated to be usefully applied through further studies for the synthesis of the macrosphelide family. 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 acts as a catalyst, a chemical building block and is used in organic synthesis. 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.Product Details of 200132-54-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Organocatalytic, Enantioselective Synthesis of Cyclohexadienone Containing Hindered Spirocyclic Ethers through an Oxidative Dearomatization/Oxa-Michael Addition Sequence was written by Reddy, Reddy Rajasekhar;Gudup, Satish Sonbarao;Ghorai, Prasanta. And the article was included in Angewandte Chemie, International Edition in 2016.Recommanded Product: 1256245-79-0 This article mentions the following:

An unprecedented enantioselective oxa-Michael reaction of α-tertiary alcs. using cinchona-alkaloid-based chiral bifunctional squaramide catalysts is reported. An oxidative dearomatization of phenol followed by an enantioselective oxa-Michael addition sequence provided a broad array of chiral sterically hindered tetrahydrofurans and tetrahydropyrans attached to a cyclohexadienone moiety in spiro fashion. In general, good yields and excellent enantioselectivities (up to 99 %) were observed The chiral oxo-cycles obtained have easily been transformed into chromans without disturbing the enantioselectivity. 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: 1256245-79-0Recommanded Product: 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 derivatives are also widely utilized as homogeneous or heterogeneous catalysts in various asymmetric processes such as Morita–Baylis–Hillman reactions, Sharpless dihydroxylation reactions, and phase-transfer catalytic reactions. 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.Recommanded Product: 1256245-79-0

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Asymmetric synthesis of Rauhut-Currier-type esters via Mukaiyama-Michael reaction to acylphosphonates under bifunctional catalysis was written by Laina-Martin, Victor;del Rio-Rodriguez, Roberto;Diaz-Tendero, Sergio;Fernandez-Salas, Jose A.;Aleman, Jose. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2018.Reference of 1256245-79-0 This article mentions the following:

A highly enantioselective organocatalytic Mukaiyama-Michael reaction of silyloxy dienes and α,β-unsaturated acyl phosphonates under bifunctional organocatalysis is presented. The new reactivity triggered by the catalyst conducted to Rauhut-Currier type esters, via a formal conjugate addition to α,β-unsaturated esters. This protocol proceeds under mild conditions with complete regioselectivity and excellent enantiocontrol. 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. 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.Reference of 1256245-79-0

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider