摘要：氰化物(含有CN-)的危害非常大，然而，氰化物(含有CN-)在生物学、制药科学、催化和环境科学中非常重要，基于此，在水中高效的检测和识别氰根离子(CN-)逐渐走进人们的视野，并成为一个热门的研究。同时，化学反应荧光探针由于其高灵敏度、特异性和低检测限，在这几年来，对它的报道屡见不鲜。但是，即便是研究到现在，对于识别氰根离子的报道，尤其是一种特殊的受体，能够有多种识别位点的同时，又能在水中可逆识别氰根离子的受体的报道相对较少。在我们的研究小组中，根据原先收集的研究资料，我们以4-溴-1,8-萘酐为原材料，经酰胺化、取代反应，氧化脱氰基和还原反应，得到了所需要的中间体化合物5，每个步骤的反应所获得的产物都通过核磁共振氢谱成功表征。最终在中间体化合物5的2位及其相对的侧位7位引入了乙腈基，反应得到了一对顺反异构体cis-7/trans-7，所得目标分子进行了核磁、高分辨质谱等表征。

关键词： 阴离子识别；萘酰亚胺；氰根离子；荧光探针；腈甲基化 

Study on the Methylation Reaction of Naphthalimide Nitrile Controlled by Trifluoromethyl Carbinol

Abstract：Cyanide (containing CN-) is very harmful. However, cyanide (containing CN-) is very important in biology, pharmaceutical science, catalysis, and environmental science. Based on this, it efficiently detects and recognizes cyanide ions in water (CN-) gradually entered people's field of vision and became a hot research. At the same time, due to its high sensitivity, specificity, and low detection limit, chemical reaction fluorescent probes have been reported in recent years. However, even in the present study, reports on the identification of cyanide ions, especially a special type of receptor, are capable of having multiple recognition sites while being able to reversibly identify receptors for cyanide ions in water. less. In our research group, based on the original research data collected, we used 4-bromo-1,8-naphthalene anhydride as the raw material, followed by amidation, substitution reaction, oxidative deacylation and reduction reaction, and the desired intermediate was obtained. Compound 5, the product obtained from the reaction of each step was successfully characterized by nuclear magnetic resonance spectroscopy. Finally, the acetonitrile group was introduced into the 2 position of the intermediate compound 5 and the 7 position of its opposite side. The reaction resulted in a pair of cis-trans isomer cis-7/trans-7. The obtained target molecule was subjected to nuclear magnetic resonance and high resolution mass spectrometry.

KeyWords:  Anion recognition; naphthalimide; cyanide ion; fluorescent probe; Nitrile methylation 

目录

1 前言 1

1.1 课题来源及背景、研究目的 1

1.2理论意义和实际应用价值 2

2 文献综述与方案论证 5

2.1文献综述 5

2.1.1 阴离子识别的意义 5

2.1.2 氰根离子识别的意义 5

2.1.3 阴离子识别的类型 6

2.1.4 氰根离子的研究进展 8

2.1.5 1，8-萘酰亚胺类荧光探针的研究进展 8

2.2 方案论证 9

3 实验部分 10

3.1 试剂与仪器 10

3.1.1 试剂 10

3.1.2仪器 11

3.2实验方法 11

3.2.1 N-正丁基-4-溴-1,8-萘酰亚胺(2)的合成 11

3.2.2 2-(2-丁基-1,3-二氧代-2,3-二氢-1H-苯并[脱]异喹啉-6-基)-2-(吡啶-2-基)乙腈(4)的合成 12

3.2.3 2-丁基-6-吡啶甲基-1H-苯并[脱]异喹啉-1,3(2H)-二酮(5)的合成 14

3.2.4 2-丁基-6-(2,2,2-三氟-1-羟基-1-(吡啶-2-基)乙基)-1H-苯并[脱]异喹啉-1,3(2H)-二酮(6)的合成 15

3.2.5探针 cis-7和 trans-7的合成 (1:0.2) 16

3.2.6 2-丁基-6-(羟基(吡啶-2-基)甲基)-1H-苯并[脱]异喹啉-1,3(2H)-二酮(8)的合成 17

3.2.7 2-丁基-1H-苯并[脱]异喹啉-1,3(2H)-二酮(9)的合成 18

4 结果与讨论 20