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可逆的な分子連結反応を鍵とする新規インターロック分子の設計と合成

基于可逆分子连接反应的新型联锁分子的设计与合成

基本信息

批准号：
21K18950
负责人：
大森建
金额：
$ 4.08万
依托单位：
Tokyo Institute of Technology
依托单位国家：
日本
项目类别：
Grant-in-Aid for Challenging Research (Exploratory)
财政年份：
2021
资助国家：
日本
起止时间：
2021-07-09 至 2024-03-31
项目状态：
已结题

项目摘要

本年度の研究においては、共有結合形成を基盤とした堅牢かつ柔軟なインターロック分子の合成経路を開拓するため、まずその基本となるシクロファン合成ユニットの合成を行った。具体的には、アントラセン構造を母核に持つ誘導体の合成を検討した。昨年度の検討において、1,5-ジブロモアントラセン誘導体とアルキン（7-octyn-1-ol）を用いた薗頭反応にて調製したビスアルキニルアントラセン誘導体が、目的とするシクロファン単位の合成前駆体となることを見出したが、その総収率に課題が残されていた。そこで、まず合成効率を向上させるための検討を集中的に行った結果、シス選択的炭素-炭素三重結合の半還元、アルコール部の酸化およびWittig反応の各段階において収率を向上させることに成功した。そして調製したテトラエン環化前駆体を第一世代のGrubbs触媒を用いた閉環オレフィンメタセシス反応（RCM）に付し、アントラセノファン誘導体を合成した。さらに合成した化合物を用い、第２の架橋環構築に向けた官能基変換および環形成反応を行い、目的とする二重架橋型アントラセノファン合成単位を収率よく得ることに成功した。またこれと並行して、上記の合成効率をさらに高めるべく、合成経路の改良を検討した結果、テトライン中間体を経由した短工程経路の実現可能性を見出し、その鍵となるnona-1,8-diyneと1,5-ジブロモアントラセン誘導体との薗頭反応において、対応するジイン誘導体の形成に有効な反応条件を見出すことに成功した。この合成法を用いれば、その後の検討に必要な合成中間体を十分量確保できるようになると期待される。

This year, a lot of research has been carried out and a total of them have been combined to form a molecular synthesis system, which is based on the development of the molecular synthesis system, the development of the molecular synthesis system, and the development of the molecular synthesis system. The specific mother nucleus is synthesized by using the mother nucleus. Last year, in the first half of the year, there was an increase in the number of people in the world (7-octyn-1-ol). In the first place, there was an increase in the size of the body in the first half of the year. Last year, in the first half of the year, there was a difference between the two parts of the body. The combination of carbon and carbon, the selected carbon-carbon triple combination and semi-addition, the acidizing effect of the acidizing part, the Wittig reaction rate of each segment, the success rate of each segment, the results of the test results, the selected carbon-carbon triple combination semi-addition, and the acidizing temperature of each segment. The first generation of Grubbs catalyst was used in the first generation of pre-environmental environmental protection equipment. The first generation of the catalyst was used in the first generation of the environmental protection plant. The first generation of the catalyst was used in the first generation of the environmental protection plant. The first generation of the catalyst was used as a catalyst for the synthesis of environmental protection products. To synthesize the compound, the second frame was used to form an inverse line in the functional group, and the double frame type was used to synthesize the compound. The rate of synthesis was successful. In this paper, the results of the parallel operation, the high frequency of the synthesis, the improvement of the performance of the synthetic route, the possibility of the short engineering route, the possibility of the short engineering route, the possibility of the synthesis, the improvement of the synthetic route, the improvement of the synthetic route, the result of the improvement of the synthetic route, the result of the improvement of the synthetic route, the result of the improvement of the synthetic route, the result of the improvement of the synthetic route, the result of the improvement of the synthetic route, the result of the improvement of the synthetic route, the result of the improvement of the synthetic route, the result of the improvement of the synthetic route, the result of the improvement of the synthetic route, the result of the improvement of the synthetic route, the result of the improvement of the synthetic route, the result of the improvement of the synthetic route, the result of the improvement of the synthetic route, the result of the improvement of the synthetic route, There is a negative condition for the formation of a successful condition. In the method of synthesis, we use the method of synthesis to make sure that the body in the synthesis is very necessary to make sure that we are looking forward to it.