Diethylsuccinoylsuccinate (original) (raw)
Diethylsuccinoylsuccinate is an organic compound with the formula [CH2C(OH)=C(CO2Et)]2 (Et = ethyl). A tetrasubstituted derivative of 1,4-cyclohexadiene, the compound is the enol tautomer of the corresponding cyclohexadione. It is produced by base-induced condensation of diethyl succinate: 2 EtO2CCH2CH2CO2Et [CH2C(OH)=C(CO2Et)]2 + 2 EtOH Diethylsuccinylsuccinate is valued as a precursor to the quinacridone pigments. For example, it reacts with two equiv of anilines to give the diamines [CH2C(N(H)Ar)=C(CO2Et)]2, which undergoes cyclization upon treatment with acid to give dihydroquinacridone.
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| dbo:abstract | Diethylsuccinoylsuccinate is an organic compound with the formula [CH2C(OH)=C(CO2Et)]2 (Et = ethyl). A tetrasubstituted derivative of 1,4-cyclohexadiene, the compound is the enol tautomer of the corresponding cyclohexadione. It is produced by base-induced condensation of diethyl succinate: 2 EtO2CCH2CH2CO2Et [CH2C(OH)=C(CO2Et)]2 + 2 EtOH Diethylsuccinylsuccinate is valued as a precursor to the quinacridone pigments. For example, it reacts with two equiv of anilines to give the diamines [CH2C(N(H)Ar)=C(CO2Et)]2, which undergoes cyclization upon treatment with acid to give dihydroquinacridone. When heated in the presence of acid, diethylsuccinoylsuccinate converts to 1,4-cyclohexanedione via hydrolysis of the esters followed by decarboxylation. (en) |
| dbo:alternativeName | 2,5-Dihydroxy-1,4-cyclohexadiene-1,4-dicarboxylic acid (en) 1,4-Bis(ethoxycarbonyl)-2,5-dihydroxy-1,4-cyclohexadiene (en) |
| dbo:iupacName | Diethyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate (en) |
| dbo:thumbnail | wiki-commons:Special:FilePath/Et2succinoylsuccinate.svg?width=300 |
| dbo:wikiPageID | 61965099 (xsd:integer) |
| dbo:wikiPageLength | 3147 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1106612775 (xsd:integer) |
| dbo:wikiPageWikiLink | dbr:Quinacridone dbc:Cyclohexadienes dbr:1,4-Cyclohexanedione dbr:1,4-cyclohexadiene dbr:Organic_compound dbr:Enol dbr:Aniline dbr:Diethyl_succinate dbr:Ethyl_group dbr:Tautomer |
| dbp:imagefile | Et2succinoylsuccinate.svg (en) |
| dbp:othernames | 14 (xsd:integer) 25 (xsd:integer) |
| dbp:pin | Diethyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate (en) |
| dbp:wikiPageUsesTemplate | dbt:Chembox dbt:Chembox_Hazards dbt:Chembox_Identifiers dbt:Chembox_Properties dbt:Fdacite |
| dct:subject | dbc:Cyclohexadienes |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q11173 dbo:ChemicalCompound |
| rdfs:comment | Diethylsuccinoylsuccinate is an organic compound with the formula [CH2C(OH)=C(CO2Et)]2 (Et = ethyl). A tetrasubstituted derivative of 1,4-cyclohexadiene, the compound is the enol tautomer of the corresponding cyclohexadione. It is produced by base-induced condensation of diethyl succinate: 2 EtO2CCH2CH2CO2Et [CH2C(OH)=C(CO2Et)]2 + 2 EtOH Diethylsuccinylsuccinate is valued as a precursor to the quinacridone pigments. For example, it reacts with two equiv of anilines to give the diamines [CH2C(N(H)Ar)=C(CO2Et)]2, which undergoes cyclization upon treatment with acid to give dihydroquinacridone. (en) |
| rdfs:label | Diethylsuccinoylsuccinate (en) |
| owl:sameAs | wikidata:Diethylsuccinoylsuccinate https://global.dbpedia.org/id/AdhQo |
| prov:wasDerivedFrom | wikipedia-en:Diethylsuccinoylsuccinate?oldid=1106612775&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/Et2succinoylsuccinate.svg |
| foaf:isPrimaryTopicOf | wikipedia-en:Diethylsuccinoylsuccinate |
| is dbo:wikiPageRedirects of | dbr:2,5-Dicarbethoxy-1,4-cyclohexanedione |
| is dbo:wikiPageWikiLink of | dbr:Quinacridone dbr:C12H16O6 dbr:1,4-Cyclohexanedione dbr:2,5-Dicarbethoxy-1,4-cyclohexanedione |
| is foaf:primaryTopic of | wikipedia-en:Diethylsuccinoylsuccinate |
