Category: 522-66-7

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In recent years increasingly stringent environmental constraints have led to a burdgeoning interest in the application of catalytic oxidation methods to fine chemicals manufacture. Whereas with bulk chemicals the choice of oxidant is often limited to molecular oxygen the economics of fine chemicals manufacture allow for a broader choice of primary oxidant. For example, relatively inexpensive single oxygen donors, such as H2O2, RO2H and NaOCI, in combination with a variety of metal catalysts provide a wide range of synthetically and economically useful oxidants. The various types of oxidation processes are outlined on the basis of type of catalyst, primary oxidant, mechanism and functional group transformation. Since fine chemicals are often relatively complex, multifunctional molecules the chemo- regio- and stereoselectivity of such processes are emphasized.

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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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A highly enantioselective approach has been developed for synthesising chiral succinimide derivatives via asymmetric Michael addition of diketones to maleimide using dihydroquinine as a catalyst in brine. The Michael adducts were obtained in yields up to 98% and with enantiomeric excesses up to 98% ee.

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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Molecular scaffolds containing alkylfluorine substituents are desired in many areas of chemical research from materials to pharmaceuticals. Herein, we report the invention of a new reagent (Zn(SO2CF2H) 2, DFMS) for the innate difluoromethylation of organic substrates via a radical process. This mild, operationally simple, chemoselective, and scalable difluoromethylation method is compatible with a range of nitrogen-containing heteroarene substrates of varying complexity as well as select classes of conjugated pi-systems and thiols. Regiochemical comparisons suggest that the CF2H radical generated from the new reagent possesses nucleophilic character.

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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Electron-deficient aromatic heterocycles, such as pyridine, quinoline, and isoquinoline, occupy a vast and rapidly expanding area of chemistry because of the obvious application of their derivatives in medicine, agriculture, polymers, and other fields. These heterocycles are rather poorly reactive towards electrophilic metalation by C?H activation and oxidative C?H activation mechanisms. The catalytic C?H functionalization of electron- deficient heterocycles remains a challenge for the synthetic chemistry community. This Focus Review highlights significant developments made in the area of transition-metal-catalyzed C?H functionalization of pi-deficient heterocycles.

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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Chemistry is the experimental and theoretical study of materials on their properties at both the macroscopic and microscopic levels.In a patent， name: Hydroquinine, Which mentioned a new discovery about 522-66-7

Free silanols on the surface of silica are the “villains”, which are responsible for detrimental interactions of those compounds and the stationary phase (i.e., bad peak shape, low efficiency) as well as low thermal and chemical stability. For these reasons,we began this review describing new silica and hybrid silica stationary phases, which have reduced and/or shielded silanols. At present, in liquid chromatography for the majority of analyses, reversed-phase liquid chromatography is the separationmode of choice. However, the needs for increased selectivity and increased retention of hydrophilic bases have substantially increased the interest in hydrophilic interaction chromatography (HILIC). Therefore, stationary phases and this mode of separation are discussed. Then, non-silica stationary phases (i.e., zirconium oxide, titanium oxide, alumina and porous graphitized carbon), which afford increased thermal and chemical stability and also selectivity different from those obtained with silica and hybrid silica, are discussed. In addition, the use of these materials in HILIC is also reviewed.

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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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The critical point and vapor pressure of pharmaceuticals are required in the calculation of their solubility in supercritical fluids by using an equation of state. The experimental critical point of many pharmaceuticals are not accessible due to their temperature sensitivity, also the experimental vapor pressure of many pharmaceuticals are not available at temperatures at which the supercritical extraction is usually accomplished. In this study, four group contribution methods are used to estimate the critical point and acentric factor of eight pharmaceuticals. The estimated properties are evaluated in predicting the vapor pressure and enthalpy of sublimation of the pharmaceuticals by using the Peng Robinson equation of state. The most accurate critical points are employed to calculate the solubility of the pharmaceuticals in the supercritical CO2 by using the Peng Robinson equation combined with two mixing rules. The AARD of 7.28% indicates the good performance of the Wong Sander mixing rule.

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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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The study of hydroquinine, a Cinchona alkaloid, by analytical TLC (silica gel) in a mixture of dichloromethane and methanol (9/1, v/v) has shown that a new compound, with a higher R(F) value, is formed during the migration. Its structure has been elucidated and was shown to be the hydrochloride salt of the alkaloid, which behaves like a tight ion-pair. X-ray analysis showed the unit cell to contain two independent monoprotonated hydroquinine hydrochloride ion-pairs, as well as two independent benzene molecules from the crystallisation solvent. The chloride ion appeared to be trapped in a positive cavity between the protonated nitrogen of the quinuclidine ring and the methoxy group of the quinoline ring. The geometry of the salt may explain its apparent lipophilicity. (C) 2001 Elsevier Science B.V.

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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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A new method has been developed for the synthesis of 2-alkylidenequinuclidines based on a silver triflate catalysed intramolecular hydroamination of 4-(prop-2-ynyl)piperidines. Monosubstituted piperidines reacted less efficiently than cis-disubstituted piperidines, and the reaction was selective for an alkyne moiety, even in the presence of a vinyl group at the 3-position. The hydroamination occurred readily with a terminal alkyne, as well as with an internal alkyne bearing an aliphatic or aromatic group at the terminal carbon atom. Using this silver-catalysed cyclization, a short procedure was developed for the relay synthesis of the cinchona alkaloids dihydroquinidine and dihydroquinine. We report the synthesis of (enantiomerically pure) 2-alkylidenequinuclidines by an intramolecular hydroamination reaction catalysed by silver triflate. After cyclization to the appropriate quinuclidines, the cinchona alkaloids dihydroquinidine and dihydroquinine were obtained in a two-step procedure.

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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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The present invention relates to a highly enantioselective process for the preparation of enantiomerically pure cyclopentane- and -pentene beta-amino acids of the general formula (I) STR1 in which A and L, A and D or E and L, D and E, R2, R3, T and R1 have the meaning given in the description.

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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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The aminohydroxylation of alkenes provides beta-amino alcohols (vicinal amino alcohols). A number of alkene aminohydroxylation protocols (and those of related reactions termed oxyamination and aminooxygenation), predominantly enabled by transition-metal catalysis, are described in this chapter, which focuses on literature published in the period 1996-2015. Cyclic and acyclic compounds containing vicinal amino alcohols and derivatives thereof can be prepared from alkenes with good regio-, diastereo-, and enantioselectivity.

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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI