化工进展 ›› 2015, Vol. 34 ›› Issue (08): 3113-3117.DOI: 10.16085/j.issn.1000-6613.2015.08.033

• 精细化工 • 上一篇    下一篇

6-(4-甲基-3-戊烯基)-2,3-环氧基-2,3-二氢萘-1,4-二醌的合成

韩莉1, 陆强1, 罗金岳1,2, 柳华锋1, 刘祖广3   

  1. 1 南京林业大学化学工程学院, 江苏 南京 210037;
    2 江苏省生物质绿色燃料与化学品重点实验室, 江苏 南京 210037;
    3 广西林产化学与工程重点实验室, 广西 南宁 530006
  • 收稿日期:2015-02-03 修回日期:2015-03-24 出版日期:2015-08-05 发布日期:2015-08-05
  • 通讯作者: 罗金岳,教授,主要研究方向为林产化学加工。E-mail luojinyue@njfu.com.cn。
  • 作者简介:韩莉(1991—),女,硕士研究生。E-mail 920006597@qq.com。
  • 基金资助:
    广西林产化学与工程重点实验室重点项目(GXFC13-01)及江苏高校优势学科建设工程项目。

Synthesis of 6-(4-methylpent-3-enyl)-2,3-epoxy-2,3-dihydronaphthalene-1,4-dione

HAN Li1, LU Qiang1, LUO Jinyue1,2, LIU Huafeng1, LIU Zuguang3   

  1. 1 College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu, China;
    2 Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, Nanjing 210037, Jiangsu, China;
    3 Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530006, Guangxi, China
  • Received:2015-02-03 Revised:2015-03-24 Online:2015-08-05 Published:2015-08-05

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

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

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