2-溴-3-甲基-1,4-萘醌与 1,3-丙二硫醇反应中新型环氧化物的形成。
Novel epoxide formation in the reaction of 2-bromo-3-methyl-1,4-naphthoquinone with 1,3-propanedithiol.
机构信息
Department of Chemistry, Occidental College, Los Angeles, CA 90041, USA.
出版信息
Bioorg Med Chem Lett. 2010 Dec 15;20(24):7226-9. doi: 10.1016/j.bmcl.2010.10.098. Epub 2010 Oct 26.
PMID:21067919
Abstract
A novel epoxide 2 was formed as the major product in the reaction of 2-bromo-3-methyl-1,4-naphthoquinone with 1,3-propanedithiol in the presence of triethylamine in 92% yield. Molecular oxygen is suggested to be the source of the added oxygen in 2, an oxidation product of its precursor 3. A strong base such as triethylamine is required to abstract the methyl hydrogen of 1,4-naphthoquinones, leading to the formation of 3 as well as 2.
摘要
在三乙胺的存在下，2-溴-3-甲基-1,4-萘醌与 1,3-丙二硫醇反应，生成主要产物新型环氧化物 2，产率为 92%。分子氧被认为是 2（其前体 3 的氧化产物）中加入氧的来源。强碱如三乙胺需要从 1,4-萘醌中提取甲基氢，从而形成 3 和 2。
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