摘要环糊精是由6-12个D-吡喃葡萄糖单元通过α-1,4糖苷键首尾相连而成的环状寡聚糖，不仅可以作为药物载体、催化剂、分子机器或分子反应器，而且可以作为手性拆分剂,受到人们广泛的关注。但天然环糊精在研究和应用中存在各种局限，通过对其改性修饰，可以增强其手性拆分能力和识别能力，拓宽其应用范围。在查阅大量文献之后，我们设计合成了一种羟烷基三唑基和咪唑鎓基修饰的新型双取代正电型环糊精。合成步骤为:以β-环糊精为原料，通过磺化、叠氮化、再磺化、咪唑环的亲核取代、与1-炔丁醇的点击反应、阴离子交换得产物6A-(4-羟乙基)-1,2,3-三氮唑-6C-[1-(2-甲氧基乙基)]咪唑鎓基-β-环糊精氯盐。各步产物通过红外光谱、核磁共振验证。62957

毕业论文关键词   双取代   正电型β-环糊精  羟烷基三唑基 

毕业设计说明书（论文）外文摘要

Title  Development of hydroxyl alkyltriazolyl and imidazolium disubstituted cyclodextrins via click chemistry

Abstract Cyclodextrins (CDs) are cyclic oligosaccharides containing 6 to 12 α-D- glucopyranoside units joined by α-1,4 glucosidic linkages. They have been widely used not only as drug deliveries, catalysts, molecular machines and molecular reactors, but also as chiral selectors. However, natural CDs have much limitation in research and application such as low aqueous solubility and chiral recognition ability. Through modification, the CD derivatives can attain stronger chiral selectivity and recognition capability, thereby extending the application fields. Based on many previous literatures, a new positively charged disubstituted β-cyclodextrin (6A-[4-ethoxyl-1,2,3-triazole]-6C-[1-(2-methoxyethyl)-imidazolium]-β-CD) modified by hydroxyl alkyltriazolyl and imidazolium has been designed and synthesized by click chemistry. In our research, β-CD was chosen as the starting material and the product was prepared by sulfonation of β-CD, azidation, sulfonation again, nucleophilic substitution by imidazole ring, click reaction with 3-butyn-1-ol and anion exchange. The products of all steps are characterized by IR and NMR.

Keywords  disubstituted,  positively charged β-cyclodextrin,  hydroxyl alkylimidazolium  

1  绪论 1

1.1 环糊精的发现和发展 1

1.2 环糊精的结构、性质与应用 1

1.2.1 环糊精的结构 1

1.2.2环糊精的物理性质 2

1.2.3环糊精的化学性质 4

1.2.4 环糊精的主要应用 5

1.3 环糊精衍生物 6

1.3.1 电中性和负电型β-环糊精衍生物 8

1.3.2 正电型β-环糊精衍生物 8

1.4 本论文的研究内容 9

2  原理和方案设计 9

2.1 方案简述 10

2.2 原料和催化剂的合成路线 11

2.3 新型双取代正电型环糊精衍生物合成路线 12

3.实验部分 13

3.1 实验试剂 13

3.2 实验仪器 14

3.3合成实验 14

3.3.1对甲基苯磺酰咪唑的合成 14