基础杯吡咯合成 - 慧知文库.doc

 HYPERLINK  基础杯吡咯合成 原文地址：/view/1f8d5076d9e80c251af28d82d445c64c.html 摘要 杯吡咯是由吡咯环和 sp3 杂化碳原子通过吡咯环 α 位连接而组成的大环化合 物。 由于其结构和性能方面具有很多的特异之处，杯吡咯构成一类别具特色的新 型杯状化合物。它可以络合阴离子和中性分子，从而应用于超分子化学领域。 本论文主要对以下几个方面进行了研究： 1)以催化剂酸、反应溶剂、反应温度三方面作为考察因素，得到杯吡咯合成 的最佳条件：以浓盐酸为催化剂，甲醇为反应溶剂，室温下合成出来了八甲基、 八乙基、四环戊基、四环己基四种杯[4]吡咯，产率分别为：85.33%，53.14%， 74.76%，61.85%。 2)通过质谱和核磁数据对四种杯[4]吡咯的分子结构进行了确认， 并利用高效 液相色谱法，使用峰面积归一化原理计算四种杯吡咯的纯度分别为 91.19%,93.76%,89.75%,89.13%； 3)在无水无过氧化物的四氢呋喃体系中， 八甲基杯[4]吡咯与N-溴代丁二酰亚 胺加热回流2 h,合成了八溴-八甲基杯[4]吡咯，产率42.51%。 4)用八溴-八甲基杯[4]吡咯大环化合物作为分子主体,以四丁基氟化铵为客 体,通过紫外扫描图表征了杯[4]吡咯与氟离子之间的多氢键作用的分子识别。 关键词：杯吡咯；合成；条件优化；分子识别 I Abstract The calixpyrrole is macrocyclic compounds with the pyrrole ring and sp3 hybridized carbon atom connection via α site in pyrrole ring. Because in their structure and performance there are much differences, the calixpyrrole consists of a distinctive and new category calix-compounds. It can be complex anions and neutral molecules, which applies to the field of supramolecular chemistry. The following aspects have been studied in this essay: 1) The acid catalyst, the reaction solvent and the reaction temperature have been investigated to find out the optimal condition. In the presence of concentrated hydrochloric acid catalyst, methanol and at room temperature, four spieces of synthesized calix[4]pyrroles，namely，meso-octamethyl calix [4] pyrrole, meso-octaethylcalix [4] pyrrole, tetrapentyl calix [4] pyrrole, tetracyclohexyl calix [4] pyrrole are obtained. And their yields are 85.33%, 53.14%, 74.76%, 61.85% respectively. 2) The molecular structures of four species of calix[4]pyrroles were confirmed by MS and 1HNMR. The purity of compounds were 91.19%, 93.76%, 89.75%, 89.13% respectively which were calculated through peak area normalization by HPLC method. 3) In anhydrous tetrahydrofuran system, octabromo- oxtamentyl calix [4] pyrrole was synthesized by refluxing octamethyl calix[4]pyrrole with NBS in 2 hour. And the yield of product is 42.51%. 4) The multi-hydrogen inte