Radical-initiated oxygenation of flavonols by dioxygen

被引:19
作者
Kaizer, J
Speier, G [1 ]
机构
[1] Univ Veszprem, Dept Organ Chem, H-8201 Veszprem, Hungary
[2] Hungarian Acad Sci, Res Grp Petrochem, H-8201 Veszprem, Hungary
基金
匈牙利科学研究基金会;
关键词
quercetinase; flavonol oxidation; TEMPO; galvinoxyl; dioxygenase model;
D O I
10.1016/S1381-1169(01)00095-4
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In the presence of free radicals, such as 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) and 2,6-di-tert-butyl-a-(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien- 1-ylidene)-p-tolyloxyl (galvinoxyl), flavonols undergo catalytic oxygenation to the corresponding depsides (phenolic carboxylic acid eaters), with concomitant evolution of CO. The oxygenolysis was performed in aprotic solvents (DMF, MeCN) and was followed by Glc. The results of oxygenation of 4 ' -substituted flavonols show that the formation of flavonoxy species is the key step in the activation process of the substrate, and that electron-releasing substituents enhance the reaction rate. (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:33 / 36
页数:4
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