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McMillan Catalyst
In organic chemistry, organocatalysis is a form of catalysis in which the rate of a chemical reaction is increased by an organic catalyst. This "organocatalyst" consists of carbon, hydrogen, sulfur and other nonmetal elements found in organic compounds.Special Issue: Because of their similarity in composition and description, they are often mistaken as a misnomer for enzymes due to their comparable effects on reaction rates and forms of catalysis involved. Organocatalysts which display secondary amine functionality can be described as performing either enamine catalysis (by forming catalytic quantities of an active enamine nucleophile) or iminium catalysis (by forming catalytic quantities of an activated iminium electrophile). This mechanism is typical for covalent organocatalysis. Covalent binding of substrate normally requires high catalyst loading (for proline-catalysis typically 20–30 mol%). Noncovalent interactions such as hydrogen-bonding facilitates low ca ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Liebig Oxamid Synthese Erste Organokat Reaktion
Justus Freiherr von Liebig (12 May 1803 – 20 April 1873) was a German scientist who made major contributions to agricultural and biological chemistry, and is considered one of the principal founders of organic chemistry. As a professor at the University of Giessen, he devised the modern laboratory-oriented teaching method, and for such innovations, he is regarded as one of the greatest chemistry teachers of all time. He has been described as the "father of the fertilizer industry" for his emphasis on nitrogen and trace minerals as essential plant nutrients, and his formulation of the law of the minimum, which described how plant growth relied on the scarcest nutrient resource, rather than the total amount of resources available. He also developed a manufacturing process for beef extracts, and with his consent a company, called Liebig Extract of Meat Company, was founded to exploit the concept; it later introduced the Oxo brand beef bouillon cube. He popularized an ear ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Proline
Proline (symbol Pro or P) is an organic acid classed as a proteinogenic amino acid (used in the biosynthesis of proteins), although it does not contain the amino group but is rather a secondary amine. The secondary amine nitrogen is in the protonated form (NH2+) under biological conditions, while the carboxyl group is in the deprotonated −COO− form. The "side chain" from the α carbon connects to the nitrogen forming a pyrrolidine loop, classifying it as a aliphatic amino acid. It is non-essential in humans, meaning the body can synthesize it from the non-essential amino acid L-glutamate. It is encoded by all the codons starting with CC (CCU, CCC, CCA, and CCG). Proline is the only proteinogenic secondary amino acid which is a secondary amine, as the nitrogen atom is attached both to the α-carbon and to a chain of three carbons that together form a five-membered ring. History and etymology Proline was first isolated in 1900 by Richard Willstätter who obtained the amino ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hajos–Parrish–Eder–Sauer–Wiechert Reaction
The Hajos–Parrish–Eder–Sauer–Wiechert reaction in organic chemistry is a proline catalysed asymmetric aldol reaction. The reaction is named after its principal investigators, Zoltan Hajos others, from Hoffmann-La RocheZ. G. Hajos, D. R. Parrish, German Patent DE 2102623 1971 and Schering AG. Discovered in the 1970s the original Hajos-Parrish catalytic procedure – shown in the reaction equation, leading to the optically active bicyclic ketol – paved the way of asymmetric organocatalysis. The Eder-Sauer-Wiechert modification lead directly to the optically active enedione, through the loss of water from the bicyclic ketol shown in figure. It has been used extensively as a tool in the synthesis of steroids and other enantiomerically pure molecules. In the original reaction shown in the figure above naturally occurring chiral proline is the chiral catalyst in an Aldol reaction. The starting material is an achiral triketone and it requires just 3% of proline to obtain ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Stetter Reaction
The Stetter reaction is a reaction used in organic chemistry to form carbon-carbon bonds through a 1,4-addition reaction utilizing a nucleophilic catalyst.Stetter, H. ''Angew. Chem. Int. Ed.'' 1976, ''15'', 639. While the related 1,2-addition reaction, the benzoin condensation, was known since the 1830s, the Stetter reaction was not reported until 1973 by Dr. Hermann Stetter.Stetter, H. and Schreckenberg, M. ''Angew. Chem. Int. Ed. Engl.'' 1973, ''12'', 81. The reaction provides synthetically useful 1,4-dicarbonyl compounds and related derivatives from aldehydes and Michael acceptors. Unlike 1,3-dicarbonyls, which are easily accessed through the Claisen condensation, or 1,5-dicarbonyls, which are commonly made using a Michael reaction, 1,4-dicarbonyls are challenging substrates to synthesize, yet are valuable starting materials for several organic transformations, including the Paal–Knorr synthesis of furans and pyrroles. Traditionally utilized catalysts for the Stetter reactio ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Thiazolium Salt
Thiazole, or 1,3-thiazole, is a heterocyclic compound that contains both sulfur and nitrogen. The term 'thiazole' also refers to a large family of derivatives. Thiazole itself is a pale yellow liquid with a pyridine-like odor and the molecular formula C3H3NS. The thiazole ring is notable as a component of the vitamin thiamine (B1). Molecular and electronic structure Thiazoles are members of the azoles, heterocycles that include imidazoles and oxazoles. Thiazole can also be considered a functional group. Oxazoles are related compounds, with sulfur replaced by oxygen. Thiazoles are structurally similar to imidazoles, with the thiazole sulfur replaced by nitrogen. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. This aromaticity is evidenced by the chemical shift of the ring protons in proton NMR spectroscopy (between 7.27 and 8.77 ppm), clearly indicating ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
DABCO
DABCO (1,4-diazabicyclo .2.2ctane), also known as triethylenediamine or TEDA, is a bicyclic organic compound with the formula N2(C2H4)3. This colorless solid is a highly nucleophilic tertiary amine base, which is used as a catalyst and reagent in polymerization and organic synthesis. It is similar in structure to quinuclidine, but the latter has one of the nitrogen atoms replaced by a carbon atom. Reactions The p''K''a of DABCOsup>+ (the protonated derivative) is 8.8, which is almost the same as ordinary alkylamines. The nucleophilicity of the amine is high because the amine centers are unhindered. It is sufficiently basic to promote C–C coupling of terminal acetylenes, for example, phenylacetylene couples with electron-deficient iodoarenes. : Catalyst DABCO is used as a base-catalyst for: *formation of polyurethane from alcohol and isocyanate functionalized monomers and pre-polymers. * Baylis-Hillman reactions of aldehydes and unsaturated ketones and aldehydes. : Lewis ba ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Esterification
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. They perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties. '' Nomenclature Etymology The ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Knoevenagel Condensation
In organic chemistry, the Knoevenagel condensation () reaction is a type of chemical reaction named after German chemist Emil Knoevenagel. It is a modification of the aldol condensation. A Knoevenagel condensation is a nucleophilic addition of an active hydrogen compound to a carbonyl group followed by a dehydration reaction in which a molecule of water is eliminated (hence ''condensation''). The product is often an α,β-unsaturated ketone (a conjugated enone). In this reaction the carbonyl group is an aldehyde or a ketone. The catalyst is usually a weakly basic amine. The active hydrogen component has the form * or for instance diethyl malonate, Meldrum's acid, ethyl acetoacetate or malonic acid, or cyanoacetic acid. * , for instance nitromethane. where Z is an electron withdrawing group. Z must be powerful enough to facilitate deprotonation to the enolate ion even with a mild base. Using a strong base in this reaction would induce self-condensation of the aldehyde o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Piperidine
Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic compound, heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, and typical of amines. The name comes from the genus name ''Piper (genus), Piper'', which is the Latin word for Black pepper, pepper. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring Solenopsin, solenopsins. Production Piperidine was first reported in 1850 by the Scottish chemist Thomas Anderson (chemist), Thomas Anderson and again, independently, in 1852 by the French chemist Auguste André Thomas Cahours, Auguste Cahours, who named it. Both of them obtained piperidine by reacting piperine with nitric acid. Industrially, piperidine is produced by the hydrogenation o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
