SEGPHOS (original) (raw)
SEGPHOS（セグフォス、IUPAC名:5,5'-ビス(ジフェニルホスフィノ)－4,4'-ビ-1,3-ベンゾジオキソール）は、不斉合成に用いられる光学活性な配位子。
| Property | Value |
|---|---|
| dbo:abstract | SEGPHOS (systematický název 4,4'-bi-1,3-benzodioxol-5,5'-diylbis(difenylfosfan), sumární vzorec C38H28O4P2), je organická sloučenina fosforu, chirální ligand vyvinutý společností Takasago k použití v asymetrické syntéze. Byl vyvinut později než BINAP a zkoumán z důvodu menšího diedrálního úhlu mezi aromatickými jádry. Bylo předpovězeno a následně potvrzeno zvýšení enantioselektivity a aktivity u kovových komplexů SEGPHOS. Komerčně jsou dostupné rovněž deriváty DM-SEGPHOS (kde jsou fenylové skupiny nahrazeny 3,5-dimethylfenylovými) a DTBM-SEGPHOS (fenyly jsou nahrazeny 3,5-di-t-butyl-4-methoxyfenyly). (cs) SEGPHOS is a chiral ligand developed by Takasago that is used in asymmetric synthesis. It was developed after BINAP and was investigated since it has a narrower dihedral angle between the aromatic faces. This was predicted and then confirmed to increase the enantioselectivity and activity of metal complexes of SEGPHOS. After its commercialization, SEGPHOS and its substituted derivatives have been found to constitute a privileged ligand class for a variety of transition metal catalysts and chemical transformations beyond its original application in ruthenium-catalyzed enantioselective hydrogenation. In addition to the parent ligand bearing phenyl groups on the phosphorus atoms, the bulkier derivatives DM-SEGPHOS and DTBM-SEGPHOS are also commercially available. In DM-SEGPHOS and DTBM-SEGPHOS, the phenyl groups of SEGPHOS are replaced by 3,5-dimethylphenyl and 3,5-di-tert-butyl-4-methoxyphenyl groups, respectively. According to Takasago, as BINAP is likened to a butterfly, SEGPHOS is like a seagull that "flies higher and faster" than a butterfly. Thus the ligand was name SE(A)G(ULL) + PHOS. (en) SEGPHOS（セグフォス、IUPAC名:5,5'-ビス(ジフェニルホスフィノ)－4,4'-ビ-1,3-ベンゾジオキソール）は、不斉合成に用いられる光学活性な配位子。 (ja) SEGPHOS是一种用于不对称合成的手性配体。 它是继BINAP之后被发现的配体。SEGPHOS被测量出其芳香环之间具有较狭窄的二面角。因此SEGPHOS被预测能增加金属络合物的对映选择性与活性，以上推测后经实验被证实。 (zh) |
| dbo:alternativeName | SEGPHOS (en) 5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole (en) |
| dbo:iupacName | (2H,2′H-[4,4′-Bi-1,3-benzodioxole]-5,5′-diyl)bis(diphenylphosphane) (en) |
| dbo:thumbnail | wiki-commons:Special:FilePath/R-SEGPHOS.svg?width=300 |
| dbo:wikiPageID | 17610655 (xsd:integer) |
| dbo:wikiPageLength | 3613 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1016254817 (xsd:integer) |
| dbo:wikiPageWikiLink | dbc:Diphosphines dbr:Ligand dbr:Chirality_(chemistry) dbr:BINAP dbr:Takasago_International_Corporation dbr:Asymmetric_synthesis dbr:File:Segphos_family.png |
| dbp:imagealt | Skeletal formula of SEGPHOS (en) Space-filling model of the SEGPHOS molecule (en) |
| dbp:imagefile | R-SEGPHOS.svg (en) SEGPHOS-3D-spacefill.png (en) |
| dbp:othernames | 55 (xsd:integer) SEGPHOS (en) |
| dbp:pin | bis (en) |
| dbp:verifiedfields | changed (en) |
| dbp:verifiedrevid | 428222586 (xsd:integer) |
| dbp:watchedfields | changed (en) |
| dbp:wikiPageUsesTemplate | dbt:Chembox dbt:Chembox_Hazards dbt:Chembox_Identifiers dbt:Chembox_Properties dbt:Cascite dbt:Chemspidercite dbt:Stdinchicite |
| dcterms:subject | dbc:Diphosphines |
| gold:hypernym | dbr:Ligand |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q11173 yago:WikicatNamedPhosphines yago:Abstraction100002137 yago:Chemical114806838 yago:Fluid114939445 yago:Gas114877585 yago:Material114580897 yago:Matter100020827 yago:Part113809207 yago:Pesticide114980215 yago:Phosphine114982129 yago:PhysicalEntity100001930 yago:Relation100031921 dbo:ChemicalCompound yago:Substance100019613 |
| rdfs:comment | SEGPHOS（セグフォス、IUPAC名:5,5'-ビス(ジフェニルホスフィノ)－4,4'-ビ-1,3-ベンゾジオキソール）は、不斉合成に用いられる光学活性な配位子。 (ja) SEGPHOS是一种用于不对称合成的手性配体。 它是继BINAP之后被发现的配体。SEGPHOS被测量出其芳香环之间具有较狭窄的二面角。因此SEGPHOS被预测能增加金属络合物的对映选择性与活性，以上推测后经实验被证实。 (zh) SEGPHOS (systematický název 4,4'-bi-1,3-benzodioxol-5,5'-diylbis(difenylfosfan), sumární vzorec C38H28O4P2), je organická sloučenina fosforu, chirální ligand vyvinutý společností Takasago k použití v asymetrické syntéze. Byl vyvinut později než BINAP a zkoumán z důvodu menšího diedrálního úhlu mezi aromatickými jádry. Bylo předpovězeno a následně potvrzeno zvýšení enantioselektivity a aktivity u kovových komplexů SEGPHOS. (cs) SEGPHOS is a chiral ligand developed by Takasago that is used in asymmetric synthesis. It was developed after BINAP and was investigated since it has a narrower dihedral angle between the aromatic faces. This was predicted and then confirmed to increase the enantioselectivity and activity of metal complexes of SEGPHOS. After its commercialization, SEGPHOS and its substituted derivatives have been found to constitute a privileged ligand class for a variety of transition metal catalysts and chemical transformations beyond its original application in ruthenium-catalyzed enantioselective hydrogenation. (en) |
| rdfs:label | SEGPHOS (cs) SEGPHOS (ja) SEGPHOS (en) SEGPHOS (zh) |
| owl:sameAs | freebase:SEGPHOS yago-res:SEGPHOS wikidata:SEGPHOS http://azb.dbpedia.org/resource/اسایجیپیاچاواس dbpedia-cs:SEGPHOS dbpedia-fa:SEGPHOS dbpedia-ja:SEGPHOS dbpedia-zh:SEGPHOS https://global.dbpedia.org/id/AED3 |
| prov:wasDerivedFrom | wikipedia-en:SEGPHOS?oldid=1016254817&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/R-SEGPHOS.svg wiki-commons:Special:FilePath/SEGPHOS-3D-spacefill.png wiki-commons:Special:FilePath/Segphos_family.png |
| foaf:isPrimaryTopicOf | wikipedia-en:SEGPHOS |
| is dbo:wikiPageWikiLink of | dbr:Organogold_chemistry dbr:Krische_allylation dbr:BINAP dbr:Diphosphines |
| is foaf:primaryTopic of | wikipedia-en:SEGPHOS |
