Month: February 2024

Loupy, Andre et al. published their research in Tetrahedron Letters in 1989 | CAS: 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.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

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

 

Rice, Scott et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2021 | CAS: 6530-09-2

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

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