Tetrahydroquinoline
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Tetrahydroquinoline
Tetrahydroquinoline is an organic compound that is the semi-hydrogenated derivative of quinoline. It is a colorless oil. Use Substituted derivatives of tetrahydroquinoline are common in medicinal chemistry. Oxamniquine, dynemycin, viratmycin, and nicainoprol are bioactive tetrahydroquinolines. Typically tetrahydroquinoline derivatives are prepared by hydrogenation of the corresponding quinoline using heterogeneous catalysts. Synthesis Tetrahydroquinolines are produced by hydrogenation of quinolines. Because the hydrogenation is reversible, tetrahydroquinoline has been often examined as a hydrogen-donor solvent in coal liquifaction. Using homogeneous catalysts, asymmetric hydrogenation has been demonstrated. It can also be prepared from 1-indanone 1-Indanone is the organic compound with the formula C6H4(CH2)2CO. It is one of two isomeric benzocyclopentanones, the other being 2-indanone. It is a colorless solid. 1-Indanone is a substrate for the enzyme indanol dehydr ...
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Oxamniquine
Oxamniquine, sold under the brand name Vansil among others, is a medication used to treat schistosomiasis due to '' Schistosoma mansoni''. Praziquantel, however, is often the preferred treatment. It is given by mouth and used as a single dose. Common side effects include sleepiness, headache, nausea, diarrhea, and reddish urine. It is typically not recommended during pregnancy, if possible. Seizures may occur and therefore caution is recommended in people with epilepsy. It works by causing paralysis of the parasitic worms. It is in the anthelmintic family of medications. Oxamniquine was first used medically in 1972. It is on the World Health Organization's List of Essential Medicines. It is not commercially available in the United States. It is more expensive than praziquantel. Medical uses Oxamniquine is used for treatment of schistosomiasis. According to one systematic review, praziquantel is the standard treatment for '' S. mansoni'' infections and oxamniquine also app ...
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Chromane
Chromane (benzodihydropyran) is a heterocyclic chemical compound with the chemical formula C9H10O. Chromane is a structural feature of more complex compounds including E vitamins (tocopherols and tocotrienols), Dianin's compound, and the pharmaceutical drugs troglitazone, ormeloxifene, and nebivolol. Such compounds are sometimes described as chromans. See also * Chromene Benzopyran is a polycyclic organic compound that results from the fusion of a benzene ring to a heterocyclic pyran ring. According to current IUPAC nomenclature, the name chromene used in previous recommendations is retained; however, systemati ... (benzopyran) External links * * {{heterocyclic-stub ...
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Quinoline
Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found in plants. Over 200 biologically active quinoline and quinazoline alkaloids are identified. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance. Occurrence and isolation Quinoline was first extracted from coal tar in 1834 by German chemist Friedlieb Ferdinand Runge; he called quinoline ''leukol'' ("white oil" in Greek). Coal tar remains the principal source of commercial quinoline. In 1842, French chemist Charles Gerhardt obtained a compound by dry distilling quinine, stry ...
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Tetralin
Tetralin (1,2,3,4-tetrahydronaphthalene) is a hydrocarbon having the chemical formula C10H12. It is a partially hydrogenated derivative of naphthalene. It is a colorless liquid that is used as a hydrogen-donor solvent. Production Tetralin is produced by the catalytic hydrogenation of naphthalene. Although nickel catalysts are traditionally employed, many variations have been evaluated. Over-hydrogenation converts tetralin into decahydronaphthalene (decalin). Rarely encountered is dihydronaphthalene (dialin). Laboratory methods In a classic named reaction called the Darzens tetralin synthesis, named for Auguste Georges Darzens (1926), derivatives can be prepared by intramolecular electrophilic aromatic substitution reaction of a 1-aryl-4-pentene using concentrated sulfuric acid, Uses Tetralin is used as a hydrogen-donor solvent, for example in coal liquifaction. It functions as a source of H2, which is transferred to the coal. The partially hydrogenated coal is more solu ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Quinoline
Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found in plants. Over 200 biologically active quinoline and quinazoline alkaloids are identified. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance. Occurrence and isolation Quinoline was first extracted from coal tar in 1834 by German chemist Friedlieb Ferdinand Runge; he called quinoline ''leukol'' ("white oil" in Greek). Coal tar remains the principal source of commercial quinoline. In 1842, French chemist Charles Gerhardt obtained a compound by dry distilling quinine, stry ...
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Medicinal Chemistry
Medicinal or pharmaceutical chemistry is a scientific discipline at the intersection of chemistry and pharmacy involved with designing and developing pharmaceutical drugs. Medicinal chemistry involves the identification, synthesis and development of new chemical entities suitable for therapeutic use. It also includes the study of existing drugs, their biological properties, and their quantitative structure-activity relationships (QSAR). Medicinal chemistry is a highly interdisciplinary science combining organic chemistry with biochemistry, computational chemistry, pharmacology, molecular biology, statistics, and physical chemistry. Compounds used as medicines are most often organic compounds, which are often divided into the broad classes of small organic molecules (e.g., atorvastatin, fluticasone, clopidogrel) and "biologics" (infliximab, erythropoietin, insulin glargine), the latter of which are most often medicinal preparations of proteins (natural and recombinant ant ...
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Hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a Catalysis, catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated and unsaturated compounds, saturate organic compounds. Hydrogenation typically constitutes the addition of pairs of hydrogen atoms to a molecule, often an alkene. Catalysts are required for the reaction to be usable; non-catalytic hydrogenation takes place only at very high temperatures. Hydrogenation reduces Double bond, double and Triple bond, triple bonds in hydrocarbons. Process Hydrogenation has three components, the Saturated and unsaturated compounds, unsaturated substrate, the hydrogen (or hydrogen source) and, invariably, a catalyst. The redox, reduction reaction is carried out at different temperatures and pressures depending upon the substrate and the activity of the catalyst. Related or competing reactions The same ca ...
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Hydrogen-donor Solvent
A hydrogen-donor solvent is hydrocarbon that transfers hydrogen to hydrogen-poor substrates, such as coal. The hydrogen-poor substrates could be a solute or suspension. The classic hydrogen-donor solvent (or just donor solvent) is tetrahydronaphthalene, which converts to naphthalene by transfer of two equivalents of H2 to the substrate. The enthalpy of hydrogenation of naphthalene is relatively low, which allows the tetrahydronaphthalene to be regenerated in the presence of high pressure H2. Catalysts are often used, such as molybdenum disulfide. Related hydrogen donor solvents or solvent components are dihydrophenanthrene and tetrahydroquinoline Tetrahydroquinoline is an organic compound that is the semi-hydrogenated derivative of quinoline. It is a colorless oil. Use Substituted derivatives of tetrahydroquinoline are common in medicinal chemistry. Oxamniquine, dynemycin, viratmycin, a .... {{cbignore, bot=medic References Coal Synthetic fuel technologies ...
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Coal Liquifaction
Coal liquefaction is a process of converting coal into liquid hydrocarbons: liquid fuels and petrochemicals. This process is often known as "Coal to X" or "Carbon to X", where X can be many different hydrocarbon-based products. However, the most common process chain is "Coal to Liquid Fuels" (CTL). Historical background Coal liquefaction originally was developed at the beginning of the 20th century. The best-known CTL process is Fischer–Tropsch synthesis (FT), named after the inventors Franz Fischer and Hans Tropsch from the Kaiser Wilhelm Institute in the 1920s. The FT synthesis is the basis for indirect coal liquefaction (ICL) technology. Friedrich Bergius, also a German chemist, invented direct coal liquefaction (DCL) as a way to convert lignite into synthetic oil in 1913. Coal liquefaction was an important part of Adolf Hitler's four-year plan of 1936, and became an integral part of German industry during World War II. During the mid-1930s, companies like IG Farben and ...
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Homogeneous Catalyst
In chemistry, homogeneous catalysis is catalysis by a soluble catalyst in a solution. Homogeneous catalysis refers to reactions where the catalyst is in the same phase as the reactants, principally in solution. In contrast, heterogeneous catalysis describes processes where the catalysts and substrate are in distinct phases, typically solid-gas, respectively. The term is used almost exclusively to describe solutions and implies catalysis by organometallic compounds. Homogeneous catalysis is an established technology that continues to evolve. An illustrative major application is the production of acetic acid. Enzymes are examples of homogeneous catalysts. Examples Acid catalysis The proton is a pervasive homogeneous catalyst because water is the most common solvent. Water forms protons by the process of self-ionization of water. In an illustrative case, acids accelerate (catalyze) the hydrolysis of esters: :CH3CO2CH3 + H2O CH3CO2H + CH3OH At neutral pH, aqueous solutions of most e ...
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Asymmetric Hydrogenation
Asymmetric hydrogenation is a chemical reaction that adds two atoms of Hydrogen atom, hydrogen to a target (substrate) molecule with three-dimensional Enantioselective synthesis, spatial selectivity. Critically, this selectivity does not come from the target molecule itself, but from other reagents or catalysts present in the reaction. This allows spatial information (what chemists refer to as chirality) to transfer from one molecule to the target, forming the product as a single enantiomer. The chiral information is most commonly contained in a catalyst and, in this case, the information in a single molecule of catalyst may be transferred to many substrate molecules, amplifying the amount of chiral information present. Similar processes occur in nature, where a chiral molecule like an enzyme can catalyse the introduction of a chiral centre to give a product as a single enantiomer, such as amino acids, that a cell needs to function. By imitating this process, chemists can generate ...
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