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Ⅰ:联二萘酚、联二萘胺、联萘酚胺的合成及拆分研究 Ⅱ:辅酶Q10的合成研究

Ⅰ: The Synthesis and Resolution Research on 2, 2’-Dihydroxy-1, 1’-Binaphthyl and 2, 2’-Diamino-1, 1’-Binaphthyl and 2-Amino-2’-Hydroxy-1, 1’-Binaphthyl Ⅱ: The Synthesis Research on Coenzyme Q10

【作者】 杨会来

【导师】 李景华;

【作者基本信息】 浙江工业大学 , 药物化学, 2006, 硕士

【摘要】 本论文主要包含两部分的内容:(1)联二萘酚、联二萘胺、联萘酚胺的合成及拆分研究(2)辅酶Q10的合成研究。第一部分我们首先讨论了联萘类化合物联二萘酚、联二萘胺、联萘酚胺及其衍生物的意义和应用价值,在阐明了它们在有机合成反应中的重要性之后,我们对它们这三种物质的合成以及拆分作了详细的讨论与分析,通过比较合成与拆分方法的优劣,我们分别确定了它们各自的合成路线和拆分方法,在确定了既定方法之后,我们对其进行了合成后的化学拆分并且得到了理想的对映体e.e.值,此外我们还同时对联二萘酚、联二萘胺和联萘酚胺进行了联合拆分,达到了良好的对映体分离效果。第二部分我们综述了辅酶Q10的用途、应用前景及其合成进展,经过认真考虑和筛选我们在参考Fujita的合成方法的基础上对辅酶Q10进行了合成研究,最终得到了辅酶Q10。其中在最后两步脱砜(脱苯磺酰基)脱苄基反应和氧化后所生成的几何异构体比例方面我们作了大量的研究和分析工作,对辅酶Q10的合成具有一定的参考价值。

【Abstract】 This paper contains two parts basically:(l) The synthesis and resolution on 2,2’-dihydroxy-1,1’-binaphthyl, 2,2’-diamino-l, 1 ’-binaphthyl and 2,2’-diamino-1,1’-binaphthyl (2) The explore on how to synthesize Coenzyme Q10.In part one, we introduced the significance and application of 2,2’-dihydroxy-l,1 ’-binaphthyl,2,2’-diamino-l,r-binaphthyl and2-amino-2’-hydroxy-1,1’-binaphthyl and their racemate first, after the illumination, we maked detailed discussion and analysis about three compouds mentioned above, then we confirmed their own route of synthesis and resolution through comparison of every route’s merit and disadvantage. After finishing synthesized them, we resolved them by chemical method, the enantiomeric excess results were good, furthermore, we used High Performance Liquid Chromatography method to enantioseparate them at the same time, the results of enantioseparation were also satisfying. In part two, we summarized the use, applications foreground and preparation methods evolvement about Coenzyme Q10, after considering the synthesis methods circumspectly, we investigated the preparation of Coenzyme Q10 according to Fujita’s methods and we achieved. During the course, we did a lot of work in two aspects: how to remove benzenesulfonyl and benzyl groups, then analyzed the ratio of geometrical isomers after oxidation. It has great consult value on synthesis of Coenzyme Q10.

  • 【分类号】R914
  • 【下载频次】209
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