摘要: 近几年来，由于含氟有机物的特殊性质，使得其具有非常良好的发展潜力。而其特殊性质又决定了含氟有机物具有其他有机物所不具备的功能，使得含氟有机物在材料、药物方面应用非常广泛。这些因素使得含氟有机物尤其是芳基含氟物得到了快速的发展。在目前已知的元素当中氟原子的电负性是最大的，且范德华半径接近于氢原子，而含氟化合物独特的物化性质正是由这两种特性所决定的。由于氟原子的引入，芳香族化合物的物化性质发生了明显的改变，并由此产生了许多全新的、特别的功能。在本课题的实验研究中，我们以已有的文献为基础上选择4-溴-1,8-萘酐作为原料，经一系列酰胺化、取代反应、氧化脱氰基、还原反应，得到芳基萘酰亚胺基甲醇中间体。然后再进行氟代研究，通过SelectF氟试剂，在冰盐浴的条件下加入二乙胺基三氟化硫(DAST)作为氟化试剂，然后在室温的条件下搅拌反应。最终得到目标分子2-丁基-6-(氟(苯基)甲基)-1H-苯并[脱]异喹啉-1,3(2H)-二酮(TM)，所有中间体及目标化合物经过核磁图谱的表征。70059

毕业论文关键词：芳基氟化物；荧光探针；萘酰亚胺；氟代反应；合成

Study on Fluorination Reaction of 2-butyl-6-(hydroxy(phenyl) methyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 

Abstract: In recent years，because of  their special properties, fluorine-containing compounds are widely used in materials and pharmaceutical fields. These factors make the fluorine-containing organic compounds; especially aryl fluoride has been rapid development. Among the currently known elements, the electronegativity of the fluorine atom is the largest, and the van der Waals radius is close to the hydrogen atom, and the unique physical and chemical properties of the fluorine-containing compound are determined by abovementioned two properties. Due to the introduction of fluorine atoms to aromatic compounds, its physical and chemical propertieshave changed significantly with a number of special features. On the basis of the reported literature, using 4-bromo-1,8-naphthalene dianhydride as the starting material, the key intermediate aryl - naphthalimide methanol was prepared by a series of amidation, substitution reaction, oxidation decyanation and reduction reaction. Further, fluorination reaction of aryl naphthalimide alcohol was carried out by diethylaminosulfurtrifluoride(DAST) as a fluorination reagent under ice-salt bath and room temperature. Eventually, the target molecule2-butyl-6-(fluoro(phenyl)methyl)-1H-benzo[de]isoquinoline-1,3(2H)–dione(TM) and all intermediates were characterized by NMR spectroscopy.

Keywords: aryl fluoride; fluorescent probe; naphthalimide; fluorination reaction; synthesis

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  1, 8-萘二酰亚胺类化合物的合成 5

2.1.2  α, α-芳基萘酰亚胺腈类化合物的合成 6

2.1.3  二芳酮类化合物的合成 9

2.1.4  二芳基甲醇化合物的合成 10

2.1.5  氟代反应 10

2.2  方案论证.13

3 实验部分..14

3.1  试剂及仪器 14

3.1.1  试剂 14

3.1.2  仪器 15

3.2实验方法.............16

3.2.1 N-正丁基-4-溴-1,8-萘酰亚胺（2）的合成