22028-15-5

Basic information

• Product Name: 2,3-Dimethoxy-5-(hydroxymethyl)-2,5-cyclohexadiene-1,4-dione
• Synonyms: 2,3-Dimethoxy-5-(hydroxymethyl)-2,5-cyclohexadiene-1,4-dione
• CAS NO: 22028-15-5
• Molecular Weight: 198.175
• Mol File: 22028-15-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,3-Dimethoxy-5-(hydroxymethyl)-2,5-cyclohexadiene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dimethoxy-5-(hydroxymethyl)-2,5-cyclohexadiene-1,4-dione(22028-15-5)
• EPA Substance Registry System: 2,3-Dimethoxy-5-(hydroxymethyl)-2,5-cyclohexadiene-1,4-dione(22028-15-5)

Safety Data

• Hazardous Substances Data: 22028-15-5(Hazardous Substances Data)

Upstream product

• 5435-28-9 (3,4,5-trimethoxy-2-nitrophenyl)methanol 
• 122271-46-9 3-hydroxy-4,5-dimethoxybenzyl alcohol 
• 5582-62-7 1-trimethylsilyloxy-2-propyne 
• 5222-73-1 3,4-dimethoxy-3-cyclobutene-1,2-dione 
• 727-73-1 3,4-Dimethoxy-2,5-dinitro-benzylalkohol 
• 127998-58-7 2,3-dimethoxy-5-((trimethylsilyl)methyl)-1,4-benzoquinone 
• 111394-55-9 3-<(tert-butyldimethylsilyl)oxy>-4,5-dimethoxybenzyl alcohol 
• 22028-03-1 2,5-Dinitro-vanillin-dimethylacetal 
• 22028-02-0 3,4-Dimethoxy-2,5-dinitro-benzaldehyd 

Downstream Products

• 122271-54-9 3'-<(tert-butyldimethylsilyl)oxy>-3,4,4'-trimethoxy-2,5-bis(benzyloxy)-(E)-stilbene 
• 122271-49-2 3'-<(tert-butyldimethylsilyl)oxy>-3,4,4'-trimethoxy-2,5-bis(benzyloxy)-(Z)-stilbene 
• 122271-44-7 3,4-dimethoxy-2,5-bis(benzyloxy)benzyl tert-butyldimethylsilyl ether 
• 89635-21-2 3,4-dimethoxy-2,5-bis(benzyloxy)benzaldehyde 
• 122271-45-8 3,4-dimethoxy-2,5-bis(benzyloxy)benzyl alcohol 
• 122271-48-1 2-<<(tert-butyldimethylsilyl)oxy>methyl>-5,6-dimethoxy-1,4-benzoquinone 

Relevant articles and documents

Formation of reactive o-quinone methides from the reaction of trimethylsilyl(methyl)-substituted 1,4-benzoquinones with nucleophiles

o-Quinone methides are formed from the reaction of nucleophiles with trimethylsilyl(methyl)-1,4-benzoquinones. These reactive intermediates are trapped by excess nucleophile to form substituted quinones following oxidation. In addition, varying amounts of a symmetrical dimer and a xanthen derivative were observed. The influence of different nucleophiles and ring substituents on the rate of reaction have been studied, and are consistent with rate-limiting formation of a vinylogous enolate initiated by attack of the nucleophile on the silyl group. Graphical Abstract.

Isolation, Structure, and Synthesis of Combretastatin C-1

A new cell growth inhibitory (PS ED50 2.2 μg/mL) phenanthraquinone designated combretastatin C-1 (2) has been isolated from the African tree Combretum caffrum.The structure (2) assigned combretastatin C-1 was based on high-resolution mass and NMR spectral analyses and confirmed by total syntheses.Synthetic routes 5b -> 6b -> 2 and especially 5c -> 6c -> 2 proved to be quite practical.