| dbo:abstract |
NOBIN (2-amino-2'-hydroxy-1,1'-binaphthyl) is an organic molecule used for asymmetric catalysis. NOBIN is related to BINOL and other analogs by both having a chiral axis and being a scaffold for certain chemical reactions. NOBIN is an excellent catalyst for the aldol reaction producing reliable products, good yields, and excellent diastereoselectivity. Though rotation around the bond joining the rings is limited by the hydrogen atoms, enantiomerically pure NOBIN may racemize upon heating. NOBIN is prepared by oxidative cross coupling of 2-naphthol and 2-naphthylamine. The oxidative source is metal ions in solution such as Fe2+ or a Cu2+ amine complex. Once racemic NOBIN is produced, it needs to be resolved. One method for this is the use of camphorsulfonic acid, in which the basic group of NOBIN is used to form a diastereomeric salt of one enantiomer. The other enantiomer however will stay in solution. (en) |
| dbo:alternativeName |
2-Amino-2'-hydroxy-1,1'-binaphthyl (en) |
| dbo:iupacName |
2′-Amino[1,1′-binaphthalen]-2-ol (en) |
| dbo:thumbnail |
wiki-commons:Special:FilePath/NOBIN.png?width=300 |
| dbo:wikiPageID |
12060033 (xsd:integer) |
| dbo:wikiPageLength |
2780 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID |
1027076933 (xsd:integer) |
| dbo:wikiPageWikiLink |
dbr:Camphorsulfonic_acid dbr:Enantiomer dbc:Catalysts dbc:Naphthylamines dbr:Racemization dbr:Chiral_resolution dbr:2-Naphthol dbr:2-Naphthylamine dbr:BINOL dbr:Aldol_reaction dbc:2-Naphthols dbr:Asymmetric_catalysis dbr:Racemic dbr:Diastereoselectivity dbr:File:NOBIN_enantiomers.svg |
| dbp:imagefile |
NOBIN.png (en) |
| dbp:imagesize |
180 (xsd:integer) |
| dbp:othernames |
2 (xsd:integer) |
| dbp:pin |
2 (xsd:integer) |
| dbp:verifiedfields |
changed (en) |
| dbp:verifiedrevid |
440512804 (xsd:integer) |
| dbp:watchedfields |
changed (en) |
| dbp:wikiPageUsesTemplate |
dbt:Chembox dbt:Chembox_Hazards dbt:Chembox_Identifiers dbt:Chembox_Properties dbt:Clear-left dbt:Cascite dbt:Chemspidercite dbt:Stdinchicite |
| dcterms:subject |
dbc:Catalysts dbc:Naphthylamines dbc:2-Naphthols |
| gold:hypernym |
dbr:Molecule |
| rdf:type |
owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q11173 yago:WikicatCatalysts yago:Abstraction100002137 yago:Activator114723079 yago:Catalyst114723628 yago:Matter100020827 yago:Part113809207 yago:PhysicalEntity100001930 yago:Relation100031921 dbo:ChemicalCompound yago:Substance100019613 umbel-rc:ChemicalSubstanceType |
| rdfs:comment |
NOBIN (2-amino-2'-hydroxy-1,1'-binaphthyl) is an organic molecule used for asymmetric catalysis. NOBIN is related to BINOL and other analogs by both having a chiral axis and being a scaffold for certain chemical reactions. NOBIN is an excellent catalyst for the aldol reaction producing reliable products, good yields, and excellent diastereoselectivity. Though rotation around the bond joining the rings is limited by the hydrogen atoms, enantiomerically pure NOBIN may racemize upon heating. (en) |
| rdfs:label |
NOBIN (en) |
| owl:sameAs |
freebase:NOBIN yago-res:NOBIN wikidata:NOBIN wikidata:NOBIN dbpedia-sh:NOBIN dbpedia-sr:NOBIN https://global.dbpedia.org/id/4ruhP |
| prov:wasDerivedFrom |
wikipedia-en:NOBIN?oldid=1027076933&ns=0 |
| foaf:depiction |
wiki-commons:Special:FilePath/NOBIN.png wiki-commons:Special:FilePath/NOBIN_enantiomers.svg |
| foaf:isPrimaryTopicOf |
wikipedia-en:NOBIN |
| is dbo:wikiPageWikiLink of |
dbr:Organocatalysis |
| is foaf:primaryTopic of |
wikipedia-en:NOBIN |
