摘要：由于食品安全问题越来越受到人们重视，那么食品中微生物的检测就显得非常有必要，而大肠杆菌是国际上公认的卫生监测指示菌, 所以大肠杆菌的检测技术显得十分重要。本课题以2，4-二氯苯甲酸作为起始原料与甘氨酸合成2-羧基甲基氨基-4-氯苯甲酸，再与乙酸酐在乙酸钠的催化条件下合成中间产物N-乙酰基-6-氯吲哚-3-乙酸酯，中间产物N-乙酰基-6-氯吲哚-3-乙酸酯在亚硫酸钠的条件下，选择性脱去3位的乙酰基，生成的N-乙酰基-6-氯-3-吲哚啉酮与全乙酰吡喃溴代糖反应，所得产物在甲醇溶剂里经甲醇钠脱去保护基团乙酰基，最终得到目标产物6-氯-3-吲哚-β-D-葡萄糖苷，目标产物就是用来检测食品中的大肠杆菌的。并对重要的中间产物N-乙酰基-6-氯吲哚-3-乙酸酯和糖苷化反应的工艺进行优化，中间产物N-乙酰基-6-氯吲哚-3-乙酸酯的最优条件：反应质量比为，2-羧基甲基氨基-4-氯苯甲酸：乙酸钠=1:2，温度为146℃，时间为1。5h。糖苷化反应的最优条件：反应质量比为，N-乙酰基-6-氯-3-吲哚啉酮 ：全乙酰吡喃溴代糖=1:2。55，温度为0℃，时间为16h。81283

    本合成路线中所有物质均通过核磁共振（H-NMR）谱图进行结构确认。

毕业论文关键词：食品；大肠杆菌；中间体；糖苷；合成；

A microbial detection of chromogenic substrate synthesis

Abstract：As food safety issues more and more attention, then the detection of microbes in food is very necessary, and food in the detection of E。 coli is the most important。 In this paper, 2,4-dichlorobenzoic acid was used as the starting material to synthesize 2-carboxymethylamino-4-chlorobenzoic acid with glycine, and then acetic acid anhydride was synthesized under the catalytic conditions of sodium acetate。 The intermediate product N- 6-chloroindole-3-acetate, the intermediate N-acetyl-6-chloroindole-3-acetate was selectively removed from the 3-position acetyl group under the conditions of sodium sulfite, Acetyl-6-chloro-3-indolinol is reacted with whole acetylribopyran bromide, and the resulting product is removed from the protecting group with methanolyl in methanol solvent to give the target product 6-chloro-3- Indole-β-D-glucoside, the target product is used to detect E。 coli in food。 And the process of the important intermediate N-acetyl-6-chloroindole-3-acetate and glycoside was optimized, the optimum of the intermediate N-acetyl-6-chloroindole-3-acetate The reaction weight ratio was 2-carboxymethylamino-4-chlorobenzoic acid: sodium acetate = 1: 

2, the temperature was 146 ° C, and the time was 1。5 hours。 The optimal conditions for the glycoside are: the reaction weight ratio is N-acetyl-6-chloro-3-indolinolinone: whole acetyl pyran bromide = 1: 2。55, the temperature is 0 ° C and the time is 16 hours。

    All the materials in this synthetic route were confirmed by nuclear magnetic resonance (H-NMR) spectroscopy。

Key words：Escherichia coli; Health; Glycosides; Synthesis; Foods;

目录

1。绪论 1

1。1食品中微生物的检测 1

1。1。1食品安全的重要性 1

1。1。2大肠杆菌的危害 1

1。1。3大肠杆菌在食品安全中的检测方法 1

1。2中间底物的合成进展 3

1。3 糖苷化合物的合成方法 5

1。3。1 Koenigs-Knorr 合成法 5

1。3。2 Helferich 反应 6

1。3。3 Fischer 糖苷化法