4乙酰氨基3(3戊氧基)苯甲酸合成.docVIP

4乙酰氨基3(3戊氧基)苯甲酸合成 　 【摘要】 目的 改进可能具有抗流感病毒活性的化合物4乙酰氨基3(3戊氧基)苯甲酸的合成方法。方法 以间羟基苯甲酸为原料，经酯化、硝化、催化氢化、烷基化、酰化及水解6步反应制备4乙酰氨基3(3戊氧基)苯甲酸。结果 甲酯化收率86.9%;硝化反应采用硝酸/乙酸酐混酸作硝化试剂，收率23.5%;硝基还原用质量分数5%钯碳作催化剂催化氢化，收率95.8%;烷基化反应中先使酚羟基与氢化钠成盐，然后再与3溴戊烷反应，收率44.4%;酰化反应用DMAP作催化剂，采用向碎冰上倾倒反应液使产物析出的后处理方法，收率82.8%;酯水解中改用丙酮做溶剂，反应时间由15 h缩短至4 h，收率86.8%。各中间体和目标化合物结构经1HNMR确证。结论 改进的反应条件缩短了反应时间，简化了后处理步骤，为今后该类流感药物的研发奠定了基础。 毕业论文 【关键词】 流感神经氨酸酶抑制剂;4乙酰氨基3(3戊氧基)苯甲酸;间羟基苯甲酸;合成 　　2.School of Chemistry and Chemical Engineering，Hunan University，Changsha,Hunan 410082，China)Abstract:Objective To improve the synthetical method of 4(Nacetylamino)3(3pentyloxy)benzoic acid，which has been reported with certain antiinfluenza virus activity. Methods 4(Nacetylamino)3(3pentyloxy)benzoic acid was prepared by sixstep reaction of esterification，nitration，catalytic hydrogenation，alkylation，acylation，and hydrolysis with mhydroxybenzoic acid as raw material. Results The yield of esterification was 86.9%; Mixed acid of nitric acid and acetic anhydride as nitration reagent，the yield of nitration was 23.5%; 5% PdC as hydrogenation catalyst，the yield was 95.8%; In the alkylation，phenolic hydroxyl formed salt with sodium hydride，then reacted with 3bromo pentane，and the yield was 44.4 %; DMAP as catalyst，the postprocessing steps were simplified with the method of pouring the reaction solution into ice，the yield was 82.8%; The reaction time was shortened from the 15 h to 4 h with acetone as solvent in the reaction of hydrolysis，and the yield was 86.8%. The structures of all intermediates and the target compound were confirmed by 1HNMR. Conclusion The improved reaction conditions shortened the reaction time，simplified the postprocessing steps，and established the foundation for future development of this type of influenza drugs. 论文代写 　　Key words: influenza virus neuraminidase inhibitors; 4(Nacetylamino)3 (3 pentyloxy)benzoic acid; mhydroxybenzoic acid; synthesis 论文代写 　　流感是发病率和死亡率较高的一种呼吸道疾病，尤