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摘要金刚烷分子具有和金刚石内部晶格相同的结构，是一个高度对称的环状四面体笼式化合物。独特的物理和化学性质，使其在医药、高分子化工、精细化工等各领域都引起人们的高度重视。随着其合成方法的不断改进，应用前景也越来越广阔。金刚烷酮作为一种金刚烷衍生物的重要中间体，可以衍变为各种取代基的金刚烷化合物，如金刚烷胺、硝基金刚烷，广泛应用于药物和含能材料中。本文以丙二酸二乙酯、多聚甲醛为起始原料，经过环合反应合成重要中间体Meerwein酯，再经过酸催化的环合反应、臭氧化反应合成2,4,6-金刚烷三酮。此法利用小分子化合物成功地构造出含金刚烷骨架的活性中间体，可作为合成多取代金刚烷衍生物的基础步骤。而且此法只有4个步骤，操作简单，原料廉价无毒，产率也较理想。9997
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关键词 金刚烷 金刚烷三酮 四面体笼式化合物 Meerwein酯
毕业设计说明书（论文）外文摘要
Title The Synthesis of Adamantanetrione and Its Derivatives
Abstract
Adamantine is a highly symmetrical cyclic tetrahedral-cage compound with the same internal structure of diamond lattice. Because of its excellent unique physical and chemical properties, people in various fields ranging from pharmaceutical to polymer and fine chemical industry pay close attention to adamantine. With the improvement of synthetic methods, its application prospects become broader and broader. A lot of adamantane compounds with various substituents, such as amantadine and polynitroadamantanes, which are widely used in medicines and energetic materials, can be evolved by adamantanone, an important intermediate for adamantane derivatives. In this paper, Meerwein's ester, an important intermediate, was firstly synthesized by cyclization of diethyl malonate and polyformaldehyde, which were utilized as raw materials. Then, adamantanetrione was synthesized by acid-catalyzed cyclization and ozonation. In this method, reactive intermediate containing the adamantane skeleton was successfully constructed by small molecule compounds, which should be very helpful for the synthesis of polysubstituted adamantane derivatives. This method is only four steps with simple operations utilizing inexpensive and non-toxic raw materials but bringing better yield.
Keywords Adamantane Adamantanetrione Tetrahedral-cage compound Meerwein's ester
目 次
1 引言 1
1.1 金刚烷 1
1.1.1 金刚烷的性质 1
1.1.2 金刚烷的用途 1
1.2 多硝基金刚烷 2
1.2.1 多硝基金刚烷的性质 2
1.2.2 1,3,5,7-四硝基金刚烷的合成 3
1.2.3 1,2,2-三硝基金刚烷的合成 3
1.2.4 2,2,4,4-四硝基金刚烷的合成 4
1.2.5 2,2,4,4,6,6-优尔硝基金刚烷的合成 4
1.3 金刚烷胺 5
1.4 金刚烷酮 6
1.4.1 金刚烷三酮的合成 6
1.4.2 金刚烷三酮合成的机理 6
1.5 本课题提出的目的和意义 8
1.6 本文研究的主要内容 8
2 实验部分及结果与讨论 8
2.1 实验仪器及实验试剂 8
2.2 合成路线一 10
2.2.1 由多聚甲醛和丙二酸二乙酯合成Meerwein酯 10