18797-86-9Relevant academic research and scientific papers
Synthesis and biological activity of fatty acid derivatives of quinine
Kumura, Naokazu,Izumi, Minoru,Nakajima, Shuhei,Shimizu, Sakayu,Kim, Hye-Sook,Wataya, Yusuke,Baba, Naomichi
, p. 2250 - 2253 (2005)
Derivatives of quinine with fatty acids including polyunsaturated fatty acids were prepared. They showed moderate antimalarial activity as compared with quinine itself using Plasmodium falciparum. The activities were not dependent on whether the fatty acyl group was saturated or unsaturated. On the other hand, the derivatives showed significantly higher cytotoxicity against a mammary tumor cell line FM3A than quinine itself. Calculating from these data, an acetyl derivative of quinine with the shortest acyl group was found to give the highest selectivity.
Insight into the Mechanism of the Acylation of Alcohols with Acid Anhydrides Catalyzed by Phosphoric Acid Derivatives
Hayashi, Hiroyuki,Yasukochi, Shotaro,Sakamoto, Tatsuhiro,Hatano, Manabu,Ishihara, Kazuaki
, p. 5197 - 5212 (2021/04/12)
Insight into the mechanism of a safe, simple, and inexpensive phosphoric acid (H3PO4)-catalyzed acylation of alcohols with acid anhydrides is described. The corresponding in situ-generated diacylated mixed anhydrides, unlike traditionally proposed monoacylated mixed anhydrides, are proposed as the active species. In particular, the diacylated mixed anhydrides act as efficient catalytic acyl transfer reagents rather than as Br?nsted acid catalysts simply activating acid anhydrides. Remarkably, highly efficient phosphoric acid (1-3 mol %)-catalyzed acylation of alcohols with acid anhydrides was achieved and a 23 g scale synthesis of an ester was demonstrated. Also, phosphoric acid catalyst was effective for synthetically useful esterification from carboxylic acids, alcohols, and acid anhydride. Moreover, with regard to recent developments in chiral 1,1′-bi-2-naphthol (BINOL)-derived phosphoric acid diester catalysts toward asymmetric kinetic resolution of alcohols by acylation, some phosphate diesters were examined. As a result, a 31P NMR study and a kinetics study strongly supported not only the acid-base cooperative mechanism as previously proposed by other researchers but also the mixed anhydride mechanism as presently proposed by us.
9R-acyloxy quinine derivatives, preparation method therefor, application of quinine or derivatives thereof and botanical insecticides
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Paragraph 0051-0055; 0060-0066, (2020/02/17)
The invention relates to 9R-acyloxy quinine derivatives, a preparation method therefor, an application of quinine or derivatives thereof and botanical insecticides and belongs to the technical field of botanical pesticides. The 9R-acyloxy quinine derivatives disclosed by the invention are prepared through subjecting the quinine and R-COOH to an esterification reaction, have remarkable insecticidalactivity to Lepidoptera agricultural insect pests and have a remarkable control efficiency to armyworms of Lepidoptera, and part of the 9R-acyloxy quinine derivatives have an armyworm control efficiency already exceeding that of a commercialized botanical insecticide, i.e., toosendanin and can be applied to preparation of botanical insecticides for the Lepidoptera agricultural insect pests. In the prior art, the quinine is mainly used for treating human diseases induced by Plasmodium falciparum; and in the invention, discovered through researches, the quinine also has a relatively good control action on the Lepidoptera agricultural insect pests and has a remarkable control efficiency to the armyworms.
Origin of and a Solution for Uneven Efficiency by Cinchona Alkaloid-Derived, Pseudoenantiomeric Catalysts for Asymmetric Reactions
Hu, Bin,Bezpalko, Mark W.,Fei, Chao,Dickie, Diane A.,Foxman, Bruce M.,Deng, Li
supporting information, p. 13913 - 13920 (2018/10/20)
Cinchona alkaloid-derived chiral catalysts represent one of the most widely applied classes of organocatalysts, which have been successfully utilized in the promotion of a wide variety of asymmetric reactions. Cinchona alkaloids exist in nature as pseudoe
Catalytic Difluorination of Olefins
Molnár, István Gábor,Gilmour, Ryan
supporting information, p. 5004 - 5007 (2016/05/19)
Molecular editing with fluorine is a validated strategy for modulating the structure and function of organic systems. In the current arsenal of catalytic dihalogenation technologies, the direct generation of the vicinal difluoride moiety from simple olefins without a prefunctionalization step remains conspicuously absent. Herein we report a catalytic, vicinal difluorination of olefins displaying broad functional group tolerance, using inexpensive p-iodotoluene as the catalyst. Preliminary efforts toward the development of an enantioselective variant are also disclosed.
Stereodivergent organocatalytic intramolecular michael addition/ lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans
Belmessieri, Dorine,De La Houpliere, Alix,Calder, Ewen D. D.,Taylor, James E.,Smith, Andrew D.
supporting information, p. 9762 - 9769 (2014/08/18)
A stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported. Commercially available (S)-(-)-tetramisole hydrochloride gives products with hi
Recyclable fluorous cinchona alkaloid ester as a chiral promoter for asymmetric fluorination of β-ketoesters
Yi, Wen-Bin,Huang, Xin,Zhang, Zijuan,Zhu, Dian-Rong,Cai, Chun,Zhang, Wei
experimental part, p. 1233 - 1240 (2012/09/21)
A fluorous cinchona alkaloid ester has been developed as a chiral promoter for the asymmetric fluorination of β-ketoesters. It has comparable reactivity and selectivity to the nonfluorous versions of cinchona alkaloids and can be easily recovered from the
Organocatalytic activity of cinchona alkaloids: Which nitrogen is more nucleophilic?
Baidya, Mahiuddin,Horn, Markus,Zipse, Hendrik,Mayr, Herbert
supporting information; experimental part, p. 7157 - 7164 (2009/12/09)
(Chemical Equation Presented) The cinchona alkaloids 1a-d react selectively at the quinuclidine ring with benzyl bromide and at the quinoline ring with benzhydrylium ions (diarylcarbenium ions). The kinetics of these reactions have been determined photometrically or conductimetrically and are compared with analogous reactions of quinuclidine and quinoline derivatives. Quantum chemical calculations [MP2/6-31+G(2d,p)//B3LYP/6-31G(d)] show that the products obtained by attack at the quinuclidine ring (Nsp3) of quinine are thermodynamically more stable when small alkylating agents (primary alkyl) are used, while the products arising from attack at the quinoline ring (N sp2) are more stable for bulkier electrophiles (Ar2CH). In some cases, rate and equilibrium constants for their reactions with benzhydrylium ions could be determined. These data gave access to the Marcus intrinsic barriers, which are approximately 20 kJ mol-1 lower for attack at the Nsp3-center than at the Nsp2-center.
Liquid/liquid separation of polysiloxane-supported catalysts
Grunlan, Melissa A.,Regan, Katherine R.,Bergbreiter, David E.
, p. 1715 - 1717 (2008/10/09)
Liquid/liquid separation after monophasic reactions is a viable way to use and recover polysiloxane-supported catalysts. The Royal Society of Chemistry 2006.
Electrophilic fluorination mediated by cinchona alkaloids: Highly enantioselective synthesis of α-fluoro-α-phenylglycine derivatives
Mohar, Barbara,Baudoux, Jerome,Plaquevent, Jean-Christophe,Cahard, Dominique
, p. 4214 - 4216 (2007/10/03)
A decisive step forward: A one step fluorination on modified cinchona alkaloids produced a new range of enantiopure fluorinating agents that display high enantioselectivities in electrophilic fluorination. The first enantioselective synthesis of N-protect
