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金属参与的有机硒合成新方法及组装新型分子梭关键砌块的合成

The Novel Methods for the Synthesis of Organic Selenides in the Presence of Organometalics and the Synthesis of Blocks for Assemblying to New Molecular Shuttles

【作者】 黄荣新

【导师】 许新华;

【作者基本信息】 湖南大学 , 有机化学, 2003, 硕士

【摘要】 有机硒化合物由于其在有机合成转化中的重要作用及具有潜在的生物活性而备受化学家、药物学家及生物学家们的关注。对于它们的合成新方法与活性的研究是当前研究的一个热点,但是目前有些有机硒化合物的合成方法存在着一些不足之处,如需要苛刻的反应条件,或者使用有毒的原料及较多的实验步骤。我们在目前有机硒化合物合成方法的基础上,提出了使用无毒且价格便宜的锌试剂来合成烯丙基硒醚,该方法还具有操作简便、产率高等优点。炔硒醚是有机合成转化中的重要中间体,目前合成的方法一般需要十分严格的无水无氧操作且有产率不高等缺点,我们根据氢氧化铯的超强碱性,设计通过端炔与二硒醚反应来制备炔硒醚。该方法的优点在于不需无水无氧环境且操作简便,为炔硒醚的合成提供了一条有效的途径。 分子梭是构成分子机器的基础,它是当前科学研究的前沿领域。我们首次根据蛋白质和卵磷脂的结构特点提出蛰伏式分子梭与内盐式分子梭的概念并设计出两种这类型的分子梭。对这两类分子梭的关键砌块(三联吡啶二醇化合物和含磷内盐式化合物)进行合成,探讨了合成方法及反应条件对多步反应的影响。中间体和目标分子通过1HNMR、13C NMR、31P NMR等表征,并分析了分子结构与光谱数据的关系。

【Abstract】 Organic selenides have attracted more and more attentions of chemists, pharmacologists and biologists for their important role in the organic synthetic transformation and their latent biological activities. It is a hot topic in the field of their new synthetic methods and the research of their bioactivities. But there are some disadvantages in the synthetic methods of organic selenides, such as needing stern conditions for reaction, using poisonous materials and processing complicated multi-step process. We put forward a novel method for synthesizing the allyl selenides by cheaper and innoxious zinc reagents. Such method can afford high yields and has simple operations. Alkynyl selenides are a species of important intermediates in organic synthetic transformations, currently their synthetic methods need no-water and no-oxygen operations and their yields are much lower. Considering the highest basicity of cesium hydroxide, we plan to use terminal alkynes react with diaryl diselenides to afford alkynl selenides. This method has the advantages of simple operation and without worrying about the presence of water and oxygen.Molecular shuttle is the basic compound for constructing molecular machine The research in this field is in a front field of science. We firstly put forward the torpid molecular shuttle and the inner salt molecular shuttle duo to the structural character of protein and lecithin, and we have designed two species of these molecular shuttles. The blocks for constructing to these shuttles were synthesized. The infections of synthetic methods and conditions on the multi-step process are discussed. Intermediates and objective molecular synthesized are characterized by 1H NMR,13C NMR and 31P NMR, and the relationships of molecular structure and spectral data are analyzed.

  • 【网络出版投稿人】 湖南大学
  • 【网络出版年期】2004年 02期
  • 【分类号】O627
  • 【下载频次】187
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