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Electrosynthesis of cholesta-4,6-dien-3-one from cholesterol on a laboratory synthetic scale
Tetrahedron Letters ( IF 1.5 ) Pub Date : 6 January 2010 , DOI: 10.1016/j.tetlet.2009.10.106
Yu-Ya Hosokawa , Hideki Hakamata , Tomonori Murakami , Fumiyo Kusu

Cholesterol has been shown to be electrochemically oxidized at a carbon electrode to form cholesta-4,6-dien-3-one in acetonitrile [Hosokawa, Y. Y.; Hakamata, H.; Murakami, T.; Aoyagi, S.; Kuroda, M.; Mimaki, Y.; Itoh, A.; Morosawa, S.; Kusu, F. Electrochim. Acta, 2009, 54, 6412–6416]. To further expand on this reaction in the field of organic synthesis, the electrolysis conditions of cholesterol were optimized on a laboratory synthetic scale. Using a flow-through column electrolysis system, cholesta-4,6-dien-3-one was efficiently produced at the applied potential of 1.9 V versus Ag/AgCl with a flow rate of 2.5 mL/min, providing a green tool for the synthesis of cholesta-4,6-dien-3-one.

中文翻译:

在实验室合成规模上由胆固醇电合成胆甾醇4,6-dien-3-one

已显示胆固醇在碳电极上被电化学氧化,形成乙腈中的cholesta-4,6-dien-3-one [Hosokawa,YY; Hakamata,H .; 村上,T。青柳,S .; M.黑田田; Yimaki;伊藤,A。S.Morosawa; Kusu,F。Electrochim。ACTA2009年54,6412-6416。为了在有机合成领域进一步扩大该反应,在实验室合成规模上优化了胆固醇的电解条件。使用流通式柱电解系统,在2.5 V / min的流速下,相对于Ag / AgCl,在1.9 V的施加电势下有效地产生了cholesta-4,6-dien-3-one,为合成cholesta-4,6-dien-3-one。
更新日期:2017-01-31
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