Triketones
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Triketones
In organic chemistry, a triketone or trione is an organic compound containing three ketone () groups. The simplest triketones, such as cyclopropanetrione and 2,3,4-pentanetrione, are only of occasional theoretical interest. More pertinent are triacetylmethane and 2,4,6-heptanetrione. Both species exist predominantly in the enol () forms. Image:Croconic_acid.svg, Croconic acid Image:Ac3CH.svg, Triacetylmethane Image:2,4,6-heptanetrione.svg, 2,4,6-Heptanetrione Occurrence and significance Tri- and polyketones are of practical importance as intermediates in the biosynthesis of polyketides. These natural products are a major source of antibiotic An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of ...s. See also * Diketone References External links *{{Commonscatinline, Trik ...
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Cyclopropanetrione
Cyclopropanetrione or trioxocyclopropane is a little-known oxide of carbon with formula C3O3. It consists of a ring of three carbon atoms each attached to an oxygen atom with a double bond. Alternately, it can be thought as a trimer of carbon monoxide. This compound is thermodynamically unstable and has not been produced in bulk. However, it has been detected using mass spectrometry Mass spectrometry (MS) is an analytical technique that is used to measure the mass-to-charge ratio of ions. The results are presented as a ''mass spectrum'', a plot of intensity as a function of the mass-to-charge ratio. Mass spectrometry is use .... It is the neutral equivalent of the deltate anion C3O32−, known since 1975. An equivalent hydrate hexahydroxycyclopropane or cyclopropane-1,1,2,2,3,3-hexol, (-C(OH)2-)3 also exists. This contains geminal hydroxy groups. References {{Oxides of carbon Oxocarbons Cyclopropanes Triketones Cyclic ketones Conjugated ketones ...
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Triacetylmethane
Triacetylmethane is the organic compound with the formula . It is a colorless liquid that is soluble in organic solvents and in alkaline water. It readily forms an enolate. The enolate forms a variety of metal complexes related to the metal acetylacetonate Metal acetylacetonates are coordination complexes derived from the acetylacetonate anion () and metal ions, usually transition metals. The bidentate ligand acetylacetonate is often abbreviated acac. Typically both oxygen atoms bind to the metal t ...s.{{cite journal , doi=10.1016/j.ica.2008.11.017, title=Coordinating Properties of the Anionic Ligand (MeCO)2C(−)C(X)Me (X=O or NH) Toward Transition Metal(II) Centers , year=2009 , last1=Basato , first1=Marino , last2=Caneva , first2=Elisabetta , last3=Tubaro , first3=Cristina , last4=Veronese , first4=Augusto Cesare , journal=Inorganica Chimica Acta , volume=362 , issue=8 , pages=2551–2555 References Triketones Chelating agents Tridentate ligands 3-Hydroxypropena ...
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Croconic Acid
Croconic acid or 4,5-dihydroxycyclopentenetrione is a chemical compound with formula or . It has a cyclopentene backbone with two hydroxyl groups adjacent to the double bond and three ketone groups on the remaining carbon atoms. It is sensitive to light, soluble in water and ethanol and forms yellow crystals that decompose at 212 °C. The compound is acidic and loses the protons from the hydroxyl groups (p''K''a1 = and p''K''a2 = at 25 °C). The resulting anions, hydrogencroconate and croconate are also quite stable. The croconate ion, in particular, is aromatic and symmetric, as the double bond and the negative charges become delocalized over the five CO units (with two electrons, Hückel's rule means this is an aromatic configuration). The lithium, sodium and potassium croconates crystallize from water as dihydrates but the orange potassium salt can be dehydrated to form a monohydrate. The croconates of ammonium, rubidium and caesium crystallize in ...
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Triacetylmethane
Triacetylmethane is the organic compound with the formula . It is a colorless liquid that is soluble in organic solvents and in alkaline water. It readily forms an enolate. The enolate forms a variety of metal complexes related to the metal acetylacetonate Metal acetylacetonates are coordination complexes derived from the acetylacetonate anion () and metal ions, usually transition metals. The bidentate ligand acetylacetonate is often abbreviated acac. Typically both oxygen atoms bind to the metal t ...s.{{cite journal , doi=10.1016/j.ica.2008.11.017, title=Coordinating Properties of the Anionic Ligand (MeCO)2C(−)C(X)Me (X=O or NH) Toward Transition Metal(II) Centers , year=2009 , last1=Basato , first1=Marino , last2=Caneva , first2=Elisabetta , last3=Tubaro , first3=Cristina , last4=Veronese , first4=Augusto Cesare , journal=Inorganica Chimica Acta , volume=362 , issue=8 , pages=2551–2555 References Triketones Chelating agents Tridentate ligands 3-Hydroxypropena ...
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2,4,6-Heptanetrione
2,4,6-Heptanetrione is the organic compound with the formula . It is a white or colorless solid. The molecule, which exists mainly in the enol form, undergoes condensation with 1,2- diketones. The compound contributes to the flavor of strawberries. It forms a variety of metal complexes. See also *Triacetylmethane Triacetylmethane is the organic compound with the formula . It is a colorless liquid that is soluble in organic solvents and in alkaline water. It readily forms an enolate. The enolate forms a variety of metal complexes related to the metal ..., an isomer Refercences {{DEFAULTSORT:Heptanetrione, 2,4,6- Triketones Chelating agents Ligands 3-Hydroxypropenals Enols Tridentate ligands ...
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Organic Chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical ( in silico) study. The range of chemicals studied in organic chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but also containing other elements, especially oxygen, nitrogen, sulfur, phosphorus (included in ...
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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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Ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' is methyl), with the formula . Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone. Nomenclature and etymology The word ''ketone'' is derived from ''Aketon'', an old German word for ''acetone''. According to the rules of IUPAC nomenclature, ketone names are derived by changing the suffix ''-ane'' of the parent alkane to ''-anone''. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example acetone and benzophenone. These nonsystematic names are considere ...
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Functional Group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis. A functional group is a group of atoms in a molecule with distinctive chemical properties, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by covalent bonds. For repeating units of polymers, functional groups attach to their nonpolar core of carbon atoms and thus add chemical character to carbon chains. Fun ...
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Enol
In organic chemistry, alkenols (shortened to enols) are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene ( olefin) with a hydroxyl group attached to one end of the alkene double bond (). The terms ''enol'' and ''alkenol'' are portmanteaus deriving from "-ene"/"alkene" and the "-ol" suffix indicating the hydroxyl group of alcohols, dropping the terminal "-e" of the first term. Generation of enols often involves removal of a hydrogen adjacent (α-) to the carbonyl group—i.e., deprotonation, its removal as a proton, . When this proton is not returned at the end of the stepwise process, the result is an anion termed an enolate (see images at right). The enolate structures shown are schematic; a more modern representation considers the molecular orbitals that are formed and occupied by electrons in the enolate. Similarly, generation of the enol often is accompanied by "trapping" or masking of the hydroxy group as an ether, such as ...
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Polyketide
Polyketides are a class of natural products derived from a precursor molecule consisting of a chain of alternating ketone (or reduced forms of a ketone) and methylene groups: (-CO-CH2-). First studied in the early 20th century, discovery, biosynthesis, and application of polyketides has evolved. It is a large and diverse group of secondary metabolites caused by its complex biosynthesis which resembles that of fatty acid synthesis. Because of this diversity, polyketides can have various medicinal, agricultural, and industrial applications. Many polyketides are medicinal or exhibit acute toxicity. Biotechnology has enabled discovery of more naturally-occurring polyketides and evolution of new polyketides with novel or improved bioactivity. History Naturally produced polyketides by various plants and organisms have been used by humans since before studies on them began in the 19th and 20th century. In 1893, J. Norman Collie synthesized detectable amounts of orcinol by heating dehy ...
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Natural Product
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis (both semisynthesis and total synthesis) and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets. The term natural product has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients. Within the field of organic chemistry, the definition of natural products is usually restricted to organic compounds isolated from natural sources that are produced by the pathways of primary or secondary metabolism. Within the field of medicinal chemistry, the definition is often further restricted to secondary metabolites. Secondary metabolites (or specialized metabolites ...
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