- Two-step synthesis of 2-(9-Hydroxynonyl)-5,6-dimethoxy-3-methyl-1,4- benzoquinone
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2-(9-Hydroxynonyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone was readily synthesized from commercially available 3,4,5-trimethoxytoluene in two steps. First, 2,3-dimethoxy-5-methyl-1,4-benzoquinone (coenzyme Q0) was obtained in one step by treatment of 3,4,5-trimethoxytoluene with hydrogen peroxide under metal-free conditions, followed by free-radical alkylation with 10-hydroxydecanoic acid in the presence of potassium peroxodisulfate and silver nitrate in a mixed solvent (MeCN-H2O, 1:1) to afford the title compound in good yields (60%, based on coenzyme Q0). Georg Thieme Verlag Stuttgart. New York.
- Wang, Jin,Hu, Xiao,Yang, Jian
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- AgNO3-catalyzed decarboxylative cross-coupling reaction: an approach to coenzyme Q
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An efficient and general method for the synthesis of coenzyme Q compounds through the activation of the 1,4-benzoquinone Csp2-H bond has been developed. This C-C bond formation reaction proceeds readily in an open flask by the direct cross-coupling reaction of coenzyme Q0with commercially available aliphatic carboxylic acids utilizing AgNO3as a catalyst and K2S2O8as an oxidant in aqueous solution. This radical reaction is operationally simple and amenable to gram-scale synthesis.
- Luo, Wan-Yue,Lu, Bin,Qiu, Yong-Fu,Zhou, Rong-Ye,He, Yong-Jing,Wang, Jin
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supporting information
p. 8702 - 8704
(2020/06/08)
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- Synthesis and antioxidant activities of Coenzyme Q analogues
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A series of 2,3-dimethoxy-5-methyl-1,4-benzoquinones (Coenzyme Q) substituted at the C-6 position with various groups were designed and synthesized based on the Coenzyme Q10 as potent antioxidant. In vitro antioxidant activities of these compounds were evaluated and compared with commercial antioxidant Coenzyme Q10 employing DPPH assay. All these synthesized Coenzyme Q analogues are found to exhibit good antioxidant activities. Of which Compound 8b bearing a N-benzoylpiperazine group at the C-6 position showed more potent inhibition of DPPH radical than Coenzyme Q10. All these results suggested the applicability of the Coenzyme Q analogues as potent antioxidants for combating oxidative stress.
- Wang, Jin,Li, Shuo,Yang, Tao,Yang, Jian
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p. 710 - 713
(2015/02/19)
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