Abstract: The study on the new synthesis method of 6-(4-methylpent-3-enyl)-2,3-epoxy-2,3-dihydronaphthalene-1,4-dione has an important theoretical and practical significance, as it can cause inhibition of the tumor cells. The target product, 6-(4-methylpent-3-enyl)-2,3-epoxy-2,3-dihydronaphthalene-1,4-dione, was synthesized by epoxidation reaction with 6-(4-methyl-3-pentenyl) naphthalene-1,4-quinone as starting material and hydrogen peroxide as oxidizing agent. The structure of the product was identified by FT-IR, GC-MS and ¹H-NMR. The effects of amount of oxidant, reaction time, dosage of anhydrous sodium carbonate and types of solvent on reaction rate and percentage yield of the product were discussed. The optimum condition was obtained as follows:hydrogen peroxide as the oxidant, n(naphthalene-quinone):n(hydrogen peroxide):n(anhydrous sodium carbonate) = 1:8:0.5, solvent (ethanol), the reaction temperature (30℃), reaction time (2h). Under the above condition, the product yield was 83.9%.

Key words: naphthalene-quinone, alkaline hydrogen peroxide, epoxidation reaction, synthesis

摘要： 6-(4-甲基-3-戊烯基)-2,3-环氧基-2,3-二氢萘-1,4-二醌对肿瘤细胞有一定的抑制作用,研究其新的合成方法具有较重要的理论和实践意义。本文以6-(4-甲基-3-戊烯基)萘-1,4-二醌为原料,过氧化氢为氧化剂,通过环氧化反应制备了目标产物6-(4-甲基-3-戊烯基)-2,3-环氧基-2,3-二氢萘-1,4-二醌。采用FT-IR、GC-MS和¹H NMR等手段对产物进行了表征,确定了产物结构。探讨了氧化剂用量、反应时间、溶剂种类和无水碳酸钠用量对反应转化率和得率的影响,得到适宜的工艺条件为:以过氧化氢为氧化剂,n(萘二醌):n(过氧化氢):n(无水碳酸钠)=1:8:0.5,溶剂为乙醇,反应温度为30℃,反应时间为2h。在上述条件下,产物得率为83.9%。

关键词: 萘二醌, 碱性双氧水, 环氧化反应, 合成