优秀毕业论文（设计）_烯基硼酸酯的合成与转化.docVIP

摘 要 有机硼化合物在各个领域都有非常广泛的应用，本论文将重点研究烯基硼酸酯的合成及其与重氮酯的环丙烷化反应制备硼基取代环丙烷酯的转化。环丙烷骨架是自然界最小的碳环结构，有着独特的化学反应性质，在有机合成等各个领域也有着广泛的应用，将有机硼与环丙烷骨架结合到一起将会有很大的应用前景。 首先，实验进行了环丙烷化反应两种原料的制备。其中，烯基硼酸酯能够以66%的收率（文献报道的最高收率为80%）得到目标产物，并且能够大量合成。重氮酯的合成通过参考文献以较高收率制备了苯乙酸苄基重氮酯（收率：84%）和苯乙酸甲基重氮酯（收率：74%）。其次，本论文实验部分的重点是通过以上两种原料的环丙烷化反应制备手性硼基取代环丙烷酯，目前探索的反应条件能够以高收率（97%）得到干净的消旋体产物，对于手性硼基取代环丙烷酯的制备尝试，筛选了一系列溶剂及配体等，但没能得到较高ee值的产物，反应的dr值不高，需进一步探究。 关键词：烯基硼；重氮酯；硼基取代环丙烷；环丙烷化反应 Abstract Organic boron compound has widely used in various fields, this thesis will focus on the synthesis of alkenyl borate and its conversion with diazoacetates to prepare organoboron substituted cyclopropane carbonate. Cyclopropane skeleton is the smallest carbon ring structure, it has unique reactivity in the organic synthesis, also the compound which contains the cyclopropane skeleton has a wide range of applications. To combine the organic boron and the cyclopropane skeleton together into one molecular will give this kind of compounds a great market prospects. The first, we tried to prepare thesubstrates for the cyclopropanation reaction. For the synthesis of alkenyl borate, we get the target product in 66%yield (the highest reported yield of 80%), and the reaction can be carried out in large quantities. For the Synthesis of Diazoacetate, we followed the method of references to get a higher yield of benzylphenyl Diazoacetate (yield: 84%) and methylphenyl Diazoacetate (yield: 74%). The most important part of this thesis is to prepare cyclopropane carbonates through the reaction of the substratesmentioned above. For cyclopropanation reaction, we can get the racemic product at a high yield (97%) for the preparation of the chiral product, we tried mang kinds of solvents and chiral ligands ,but we did not get the product in desired high ee values, and so was the dr values. Key words: alkenyl boron; Diazoacetate; organoboron cyclopropane; cyclopropanation 目 录 1. 绪论 1 1.1 研究背景 1 1.1.1 选题目的及意义 1 1.1.2 国内外研究综述 1 1.2 设计思路 2 1.2.1 烯基硼酸酯的