3-(3-喹啉)-2-丙烯-1-醇叔丁基碳酸酯的合成研究

论文编号:HG233  论文字数:8538,页数:15

摘要：本文综述了3-(3-喹啉基)-2-丙烯-1-醇叔丁基碳酸酯近些年的几种重要方法，并确定此次毕业设计实验的合成方法：在实验室可行的条件下，经过Heck，水解，还原，酯化，得到目标产物——3-(3-喹啉基)-2-丙烯-1-醇叔丁基碳酸酯。
 首先，以3-溴喹啉和丙烯酸乙酯为原料，得到3-(3-喹啉基)-2-丙烯酸乙酯，收率为89.2%；然后进行酯的水解得到3-(3-喹啉基)-2-丙烯-1-酸，收率为88.6%；再用硼氢化钠（NaBH4）做还原剂进行酸的还原得到3-(3-喹啉基)-2-丙烯-1-醇，收率为62.4%；最后通过二碳酸二叔丁基酯（Boc酸酐）引入叔丁氧羰基，得到3-(3-喹啉基)-2-丙烯-1-醇叔丁基碳酸酯，总收率为47.2%。
 此路线经实验证明可行，是合成3-(3-喹啉基)-2-丙烯-1-醇叔丁基碳酸酯的一个重要方法。
关键词：塞红霉素；3-(3-喹啉基)-2-丙烯-1-醇叔丁基碳酸酯；中间体；合成

Abstract:  In this dissertation, we disclose our research results on the synthesis of 3-(3-Quinolyl)-2-propenyl-1-tert-butyl carbonate.
 We first introduce 3-Bromoquinoline and ethyl acrylate as the raw material in preparation of Quinoline-3-propenoic acid, ethyl ester，the phase transfer catalyst is tertrabutylammonium bromide. the yield is 89.2%.The hydrolysis of the ester obtained from the coupling reaction can provide Quinoline-3-propenoic acid .  Reacting the acid with sodium borohydride affords 3-(3-Quinolyl)-2-propen-1-ol. Alternatively, the alkynol is coupled with the di-tert-butyl dicarbonate to obtain 3-(3-Quinolyl)-2-propenyl-1-tert-butyl carbonate. The total yield is 47.2%.
 This route is certificated to be feasible in the test, which is also an important method of the synthesis of 3-(3-Quinolyl)-2-propenyl-1-tert-butyl carbonate .
Keywords: Erythromycin; 3-(3-Quinolyl)-2-propenyl-1-tert-butyl carbonate; Intermediate; Synthesis