Iodolactonization (original) (raw)

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dbo:abstract Halogenlaktonizace je druh chemické reakce, při které vzniká lakton adicí kyslíku a halogenu na dvojnou vazbu; jedná se o vnitromolekulární obdobu syntézy halogenhydrinů. Reakci objevil M. J. Bougalt v roce 1904 a stal se z ní jeden z nejúčinnějších způsobů přípravy laktonů. Nejčastěji se provádí jodlaktonizace, kdy produkt obsahuje atom či atomy jodu. Využití nachází při syntéze mnoha přírodních látek, z nichž mají některé, jako jsou vernolepin a (používané jako cytostatika) a (inhibitor pankreatické lipázy používaný při léčbě obezity) medicínské využití. Jodlaktonizaci použil také Elias James Corey při přípravě řady prostaglandinů. (cs) Iodolactonization (or, more generally, halolactonization) is an organic reaction that forms a ring (the lactone) by the addition of an oxygen and iodine across a carbon-carbon double bond. It is an intramolecular variant of the halohydrin synthesis reaction. The reaction was first reported by M. J. Bougalt in 1904 and has since become one of the most effective ways to synthesize lactones. Strengths of the reaction include the mild conditions and incorporation of the versatile iodine atom into the product. Iodolactonization has been used in the synthesis of many natural products including those with medicinal applications such as vernolepin and vernomenin, two compounds used in tumor growth inhibition, and vibralactone, a pancreatic lipase inhibitor. Iodolactonization has also been used by Elias James Corey to synthesize numerous prostaglandins. (en)
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dbp:name Halolactonization (en)
dbp:type Ring forming reaction (en)
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rdfs:comment Halogenlaktonizace je druh chemické reakce, při které vzniká lakton adicí kyslíku a halogenu na dvojnou vazbu; jedná se o vnitromolekulární obdobu syntézy halogenhydrinů. Reakci objevil M. J. Bougalt v roce 1904 a stal se z ní jeden z nejúčinnějších způsobů přípravy laktonů. (cs) Iodolactonization (or, more generally, halolactonization) is an organic reaction that forms a ring (the lactone) by the addition of an oxygen and iodine across a carbon-carbon double bond. It is an intramolecular variant of the halohydrin synthesis reaction. The reaction was first reported by M. J. Bougalt in 1904 and has since become one of the most effective ways to synthesize lactones. Strengths of the reaction include the mild conditions and incorporation of the versatile iodine atom into the product. (en)
rdfs:label Halogenlaktonizace (cs) Iodolactonization (en)
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