cas 81-53-8, 2-chloro-1,4-dihydroxyanthraquinone | Articles data ｜lookchem

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81-53-8

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Polycyclic Hydroxyquinones. Part 18. Diels-Alder Cycloadditions with Chloronaphthazarins as Model Reactions for Regiospecific Construction of the D ring of Anthracyclinones
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Echavarren, Antonio,Prados, Pilar,Farina, Francisco
p. 3162 - 3188
(2007/10/02)

Polycyclic Hydroxyquinones. Part 22. Diels-Alder Reaction with Chloro Derivatives of Anthracene-1,4,9,10-tetraone
The Diels-Alder reaction of 2-chloro- and 2,3-dichloro-anthracene-1,4,9,10-tetraones (8) and (9) with substituted buta-1,3-dienes occured at the internal double bond and gave angular adducts.The reaction of quinizarin (4) with chlorine in glacial acetic acid afforded the 2,3,4a,9a-tetrachloro-4a,9a-dihydroanthracene-1,4,9,10-tetraone (17).The cycloaddition of (17) with 2,3-dimethylbuta-1,3-diene (10) gave the fully aromatised linear adduct (19) whereas a reactive diene such as 1-methoxy-3-trimethylsilyloxybuta-1,3-diene (12) afforded the ketone (22), originating from the angular adduct.An explanation for the last result involves the ready halogen elimination in compound (17) to give (9) in the presence of a strongly nucleophilic diene.
Cano, Pilar,Farina, Francisco,Parellada, M. Dolores,Pascual, Conrado,Prados, Pilar
p. 1923 - 1928
(2007/10/02)

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17648-03-2
9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione

Chemical Properties

Boiling Point: 489.2 °C at 760 mmHg
Flash Point:249.7 °C
Density: 1.636 g/cm³
Vapor Pressure: 3.39E-10mmHg at 25°C
Refractive Index: 1.734
PSA: 74.60000
LogP: 2.52660

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