Asymmetric hydrogenation (original) (raw)
الهدرجة غير المتماثلة (بالإنجليزية: Asymmetric hydrogenation) هي تفاعل كيميائي يضيف ذرتين من الهيدروجين بشكل تفضيلي إلى أحد وجهين لجزيء ركيزة غير مشبع ، مثل ألكين أو كيتون. الانتقائية مشتقة من الطريقة التي ترتبط بها الركيزة بالمحفزات اللولبية. في المصطلحات ، ينقل هذا الارتباط المعلومات المكانية (ما يشير إليه الكيميائيون باسم chirality) من المحفز إلى الهدف ، ويفضل المنتج باعتباره متماثلًا واحدًا. يتم تطبيق هذه «الانتقائية الشبيهة بالإنزيم» على تخليق بعض العوامل الصيدلانية التجارية والكيماويات الزراعية.
.svg?width=300)
| Property | Value |
|---|---|
| dbo:abstract | الهدرجة غير المتماثلة (بالإنجليزية: Asymmetric hydrogenation) هي تفاعل كيميائي يضيف ذرتين من الهيدروجين بشكل تفضيلي إلى أحد وجهين لجزيء ركيزة غير مشبع ، مثل ألكين أو كيتون. الانتقائية مشتقة من الطريقة التي ترتبط بها الركيزة بالمحفزات اللولبية. في المصطلحات ، ينقل هذا الارتباط المعلومات المكانية (ما يشير إليه الكيميائيون باسم chirality) من المحفز إلى الهدف ، ويفضل المنتج باعتباره متماثلًا واحدًا. يتم تطبيق هذه «الانتقائية الشبيهة بالإنزيم» على تخليق بعض العوامل الصيدلانية التجارية والكيماويات الزراعية. (ar) Asymetrická hydrogenace je chemická reakce, při které se dva atomy vodíku navážou na molekulu substrátu s trojrozměrnou prostorovou selektivitou. Příčina této selektivity by neměla pocházet ze samotné molekuly substrátu, ale z jiných reaktantů nebo z katalyzátoru. Tímto se může chiralita přenést z reaktantu na substrát, čímž vznikne produkt obsahující pouze jeden enantiomer. Chiralitu obvykle zajišťuje katalyzátor, díky čemuž jedna molekula může přenést informaci o chiralitě na mnoho molekul substrátu, čímž se množství přítomné chirality navyšuje. Podobné procesy probíhají i v přírodě, kde chirální molekuly, jako jsou některé enzymy, katalyzují tvorbu chirálních center a produktů, například aminokyselin v jednom enantiomeru, který je potřebný ke správné funkci buňky. Napodobením těchto dějů lze připravit mnoho nových syntetických sloučenin interagujících s biologickými systémy konkrétním způsobem, například při vývoji léčiv a agrochemikálií. O rozvoj asymetrické hydrogenace ve výzkumu i průmyslu se zasloužili William Standish Knowles a Rjódži Nojori, kteří v roce 2001 společně obdrželi Nobelovu cenu za chemii. (cs) Asymmetric hydrogenation is a chemical reaction that adds two atoms of hydrogen to a target (substrate) molecule with three-dimensional 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 many novel synthetic molecules that interact with biological systems in specific ways, leading to new pharmaceutical agents and agrochemicals. The importance of asymmetric hydrogenation in both academia and industry contributed to two of its pioneers — William Standish Knowles and Ryōji Noyori — being awarded one half of the 2001 Nobel Prize in Chemistry. (en) |
| dbo:thumbnail | wiki-commons:Special:FilePath/3,4-Dihydroxy-L-phenylalanin_(Levodopa).svg?width=300 |
| dbo:wikiPageID | 19425312 (xsd:integer) |
| dbo:wikiPageLength | 70516 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1124102115 (xsd:integer) |
| dbo:wikiPageWikiLink | dbr:Pyrrolidine dbr:Enamine dbr:Enantiomer dbr:Enantioselective_synthesis dbr:Nobel_Prize_in_Chemistry dbr:Benzofuran dbr:Benzothiophene dbr:Alkene dbr:Hydrogen_atom dbr:Pharmaceutical_drug dbr:Rhodium dbr:Vinyl_group dbr:Ruthenium dbr:Noyori_asymmetric_hydrogenation dbr:Quinolines dbr:1,1'-Bi-2-naphthol dbr:Ryōji_Noyori dbr:Stereochemistry dbr:Cinchona dbr:Enantiomeric_excess dbr:Enzyme dbr:Furan dbr:Thiophene dbr:Homogeneous_catalyst dbr:Organocatalysis dbr:Prochiral dbr:Aromaticity dbr:Leopold_Horner dbr:Ligand dbr:Chirality dbr:Steric_hindrance dbr:Dendrimer dbr:Denticity dbr:Phosphinooxazolines dbr:Pi_bond dbr:Persistent_carbene dbr:BINAP dbr:William_Standish_Knowles dbr:Ion_exchange dbr:Alkaloids dbr:Amino_acids dbr:DIOP dbr:DIPAMP dbr:Ferrocene dbr:Oxazoline dbr:Palladium dbr:Friedel-Crafts_reaction dbr:Hantzsch_ester dbr:Heterogeneous dbr:Asymmetric_hydrogenation dbc:Hydrogenation dbr:Iridium dbr:Iron dbr:Tert-Butyloxycarbonyl_protecting_group dbr:Phosphoramidite dbc:Asymmetry dbc:Organic_reactions dbc:Chemical_processes dbr:Adsorption dbc:Green_chemistry dbr:Agrochemicals dbr:Ketones dbr:L-DOPA dbr:Bisoxazoline_ligand dbr:Trimer_(chemistry) dbr:Imines dbr:Tetrakis(3,5-bis(trifluoromethyl)phenyl)borate dbr:Aryl dbr:C2-Symmetric_ligands dbr:Phosphine dbr:Pyridines dbr:DPEN dbr:Enantiotopic dbr:Indole dbr:Mibefradil dbr:Brønsted–Lowry_acid–base_theory dbr:Nanoparticles dbr:Olefin dbr:Reagents dbr:Reaction_mechanism dbr:Regioselectivity dbr:Turnover_number dbr:Imine dbr:Tridentate_ligand dbr:Tautomers dbr:Heteroaromatic dbr:Non-coordinating_anion dbr:Transfer_hydrogenation dbr:Molecular_Symmetry dbr:Racemic dbr:Brønsted_acid dbr:Parkinson's dbr:Catalysts dbr:Diphosphine_ligand dbr:N-heterocyclic_carbene dbr:Privileged_ligand dbr:Pyrroles dbr:Pyrrolidines dbr:Pyrrolines dbr:Henri_Kagan dbr:Olefins dbr:File:(S,S)-4_Ro_67-8867.svg dbr:File:3,4-Dihydroxy-L-phenylalanin_(Levodopa).svg dbr:File:Asymmetric_Hydrogenation_of_2,3,5-substituted_N-Boc_Pyrroles.tif dbr:File:Asymmetric_Hydrogenation_of_Benzofuran.png dbr:File:Asymmetric_Hydrogenation_of_Thiophenes.tif dbr:File:Burgess's_Asymmetric_Hydrogenation_Catalyst.tif dbr:File:ChiralMonodentate.png dbr:File:Cinchonidine2d.png dbr:File:Convergent_Mechanisms_for_Asymmetric_Hydrogenation.svg dbr:File:Efficient_Asymmetric_Ketone_Hydrogenation_with_SpiroPAP.png dbr:File:Heterogeneous_Asymmetric_Hydrogenation_Pyridines.png dbr:File:Historic_Diphosphines.tif dbr:File:Indoles_Boc.tif dbr:File:Indoles_Tandem.tif dbr:File:Noyori_DiamineCatalyst.png dbr:File:OrganocatalyticAsymmetricHydrogenation_Quinoline.tif dbr:File:Partial_Roche_Synthesis_of_Mibefradil.tif dbr:File:Quadrants_Diagram_for_Asymmetric_Hydrogenation.tif dbr:File:Substrate_Specificity_in_Asymmetr...ation_of_Unfunctionalized_Olefins.png dbr:File:ZrPhosphonate_Heterogeneous_Catal...ric_Hydrogenation_of_Aryl_Ketones.png |
| dbp:align | center (en) right (en) |
| dbp:alt | A chiral monophosphine derived from BINOL (en) A chiral monophosphine derived from ferrocene (en) The historically important CAMP ligand (en) |
| dbp:b | 4 (xsd:integer) |
| dbp:caption | Effective ligand for various asymmetric-hydrogenation processes (en) A BINOL derivative (en) A ferrocene derivative (en) Generic PHOX ligand architecture (en) The CAMP ligand (en) |
| dbp:image | CAMP.tif (en) ChiralMonophosphine.tif (en) ChiralMonophosphine2.tif (en) Generic PHOX Ligand.svg (en) PO Ligand Asymmetric Hydrogenation.tif (en) |
| dbp:p | F (en) |
| dbp:width | 100 (xsd:integer) 125 (xsd:integer) 160 (xsd:integer) (31.5*3) round 0 (en) (48.2*3) round 0 (en) |
| dbp:wikiPageUsesTemplate | dbt:Anchor dbt:Center dbt:Multiple_image dbt:Reflist dbt:Use_British_English dbt:Su |
| dct:subject | dbc:Hydrogenation dbc:Asymmetry dbc:Organic_reactions dbc:Chemical_processes dbc:Green_chemistry |
| gold:hypernym | dbr:Reaction |
| rdf:type | yago:WikicatChemicalProcesses yago:ChemicalProcess113446390 yago:NaturalProcess113518963 yago:PhysicalEntity100001930 yago:Process100029677 dbo:Disease |
| rdfs:comment | الهدرجة غير المتماثلة (بالإنجليزية: Asymmetric hydrogenation) هي تفاعل كيميائي يضيف ذرتين من الهيدروجين بشكل تفضيلي إلى أحد وجهين لجزيء ركيزة غير مشبع ، مثل ألكين أو كيتون. الانتقائية مشتقة من الطريقة التي ترتبط بها الركيزة بالمحفزات اللولبية. في المصطلحات ، ينقل هذا الارتباط المعلومات المكانية (ما يشير إليه الكيميائيون باسم chirality) من المحفز إلى الهدف ، ويفضل المنتج باعتباره متماثلًا واحدًا. يتم تطبيق هذه «الانتقائية الشبيهة بالإنزيم» على تخليق بعض العوامل الصيدلانية التجارية والكيماويات الزراعية. (ar) Asymetrická hydrogenace je chemická reakce, při které se dva atomy vodíku navážou na molekulu substrátu s trojrozměrnou prostorovou selektivitou. Příčina této selektivity by neměla pocházet ze samotné molekuly substrátu, ale z jiných reaktantů nebo z katalyzátoru. Tímto se může chiralita přenést z reaktantu na substrát, čímž vznikne produkt obsahující pouze jeden enantiomer. Chiralitu obvykle zajišťuje katalyzátor, díky čemuž jedna molekula může přenést informaci o chiralitě na mnoho molekul substrátu, čímž se množství přítomné chirality navyšuje. Podobné procesy probíhají i v přírodě, kde chirální molekuly, jako jsou některé enzymy, katalyzují tvorbu chirálních center a produktů, například aminokyselin v jednom enantiomeru, který je potřebný ke správné funkci buňky. Napodobením těchto děj (cs) Asymmetric hydrogenation is a chemical reaction that adds two atoms of hydrogen to a target (substrate) molecule with three-dimensional 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 chir (en) |
| rdfs:label | هدرجة غير متماثلة (ar) Asymetrická hydrogenace (cs) Asymmetric hydrogenation (en) |
| owl:sameAs | freebase:Asymmetric hydrogenation yago-res:Asymmetric hydrogenation wikidata:Asymmetric hydrogenation dbpedia-ar:Asymmetric hydrogenation dbpedia-cs:Asymmetric hydrogenation https://global.dbpedia.org/id/4TM2h |
| prov:wasDerivedFrom | wikipedia-en:Asymmetric_hydrogenation?oldid=1124102115&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/3,4-Dihydroxy-L-phenylalanin_(Levodopa).svg wiki-commons:Special:FilePath/(S,S)-4_Ro_67-8867.svg wiki-commons:Special:FilePath/Asymmetric_Hydrogenation_of_Benzofuran.png wiki-commons:Special:FilePath/ChiralMonodentate.png wiki-commons:Special:FilePath/Cinchonidine2d.png wiki-commons:Special:FilePath/Convergent_Mechanisms_for_Asymmetric_Hydrogenation.svg wiki-commons:Special:FilePath/Efficient_Asymmetric_Ketone_Hydrogenation_with_SpiroPAP.png wiki-commons:Special:FilePath/Generic_PHOX_Ligand.svg wiki-commons:Special:FilePath/Heterogeneous_Asymmetric_Hydrogenation_Pyridines.png wiki-commons:Special:FilePath/Noyori_DiamineCatalyst.png wiki-commons:Special:FilePath/Substrate_Specificity...ation_of_Unfunctionalized_Olefins.png wiki-commons:Special:FilePath/ZrPhosphonate_Heterog...ric_Hydrogenation_of_Aryl_Ketones.png |
| foaf:isPrimaryTopicOf | wikipedia-en:Asymmetric_hydrogenation |
| is dbo:wikiPageRedirects of | dbr:Asymmetric_catalytic_reduction |
| is dbo:wikiPageWikiLink of | dbr:Enantioselective_synthesis dbr:Metal-ligand_cooperativity dbr:Ben_Feringa dbr:Biferrocene dbr:Brice_Bosnich dbr:Dehydroamino_acid dbr:Ruthenium dbr:Noyori_asymmetric_hydrogenation dbr:(S)-iPr-PHOX dbr:Ryōji_Noyori dbr:Timeline_of_Monsanto dbr:Monsanto dbr:Organorhodium_chemistry dbr:Ligand dbr:Chiral_auxiliary dbr:Slayton_A._Evans_Jr. dbr:Josiphos_ligands dbr:Phosphinooxazolines dbr:2-Methylbutanoic_acid dbr:William_Standish_Knowles dbr:DuPhos dbr:Cyclooctadiene_rhodium_chloride_dimer dbr:DIPAMP dbr:History_of_science_and_technology_in_Japan dbr:List_of_Nobel_laureates_in_Chemistry dbr:Asymmetric_hydrogenation dbr:Iridium dbr:Tetrahydroquinoline dbr:Hydrogenation dbr:Albert_Sun-Chi_Chan dbr:Diphenylethylenediamine dbr:Artificial_metalloenzyme dbr:C2-Symmetric_ligands dbr:Phospholane dbr:Process_chemistry dbr:P-Chiral_phosphine dbr:Asymmetric_catalytic_reduction |
| is foaf:primaryTopic of | wikipedia-en:Asymmetric_hydrogenation |
