Synthesis of Jellyfish-Type Macrocyclic Molecular Flask and Efficient Reaction Using the Molecular Flask

水母型大环分子瓶的合成及利用该分子瓶的高效反应

基本信息

批准号：
15550039
负责人：
NISHINO Hiroshi
金额：
$ 2.43万
依托单位：
Kumamoto University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2003
资助国家：
日本
起止时间：
2003 至 2005
项目状态：
已结题

项目摘要

This research project was proposed that an artificial molecular flask such as a cage-type mocrocyclic compound would be synthesized and a highly efficient reaction would be carried out using the molecular flask similar to that using a protein pocket in vivo. The protein pocket in vivo is a three-dimensional hole and it is an efficient reaction flask using hydrogen bond, π-electron interaction, steric repulsion, and so on. Then we planed to synthesize an original cage-type molecular macrocyclic compound using the manganese(III)-based oxidative radical macrocyclization reaction.We developed the manganese(III)-based oxidative radical macrocyclization reaction and the synthesis of up to dihydrofuran-fused fifty-membered macrocyclic compounds was achieved, This reaction is very efficient and the yield is also high. Therefore, we examined to synthesize the original cage-type molecular macrocyclic compounds using the manganese(III)-based oxidative radical macrocyclization reaction. When the c … More age-type macrocyclic compounds would be synthesized, it would be examined the following items ;1) the inclusion of a guest organic compound into the cavity of the cage-type macrocyclic compounds,2) the immobilization of the guest organic compound and reagents in the cavity using the hydrogen bond, π-electron interaction, and/or steric repulsion,3) the highly efficient reaction of the guest organic compound with reagents in the cavity,4) the extraction and separation of the products after the reaction,5) the recovery and reuse of the cage-type macrocyclic compounds.Although the cage-type macrocyclic compounds were not synthesized, sixty-five-membered cyclophene-type macrocyclic compounds were prepared. In addition, the synthesis of nine- to eighteen-membered microdiolides were achieved. Furthermore, many new guest organic molecules were synthesized.In the near future, we will plane to investigate the functional ability of the synthesized cyclophene-type macrocyclic compounds. In the event, we will achieve the synthesis of cage-type molecular macrocyclic compounds and investigate the functional ability for the biomimetic molecular flask. Finally, we will develop the highly stereoselective organic reactions using the cage-type molecular macrocyclic compounds. Less

该研究项目提出合成笼型大环化合物等人工分子瓶，并使用该分子瓶进行类似于体内蛋白质口袋的高效反应。三维孔，它是一个利用氢键、π电子相互作用、空间斥力等的高效反应瓶。然后我们计划利用锰(III)基合成原始的笼型分子大环化合物。氧化自由基大环化反应。我们开发了锰(III)基氧化自由基大环化反应，实现了最多二氢呋喃稠合的五十元大环化合物的合成，该反应非常高效，收率也很高。研究人员利用锰（III）基氧化自由基大环化反应合成了原始的笼型分子大环化合物，当笼型大环化合物生成时。合成时，将检查以下项目；1）客体有机化合物纳入笼型大环化合物的空腔中，2）利用氢键π将客体有机化合物和试剂固定在空腔中-电子相互作用，和/或空间排斥，3）客体有机化合物与腔内试剂的高效反应，4）反应后产物的萃取和分离，5）笼的回收和再利用-大环型虽然没有合成笼型大环化合物，但制备了65元环烯型大环化合物，此外还合成了9至18元小二内酯，此外还合成了许多新的客体有机分子。在不久的将来，我们将计划研究所合成的环烯型大环化合物的功能能力。最终，我们将实现笼型分子大环化合物的合成，并研究其功能能力。最后，我们将利用笼型分子大环化合物开发高度立体选择性的有机反应。