第一部分：基於葡萄醣胺分子之掌性配位基的合成研究 第二部分：具螯合鋅離子基團之螢光性咪唑衍生物的合成研究

Part I: Synthetic study of glucosamine-based chiralligands Part II: Synthetic study of fluorescent imidazole derivatives with Zn(II) chelating ligand

邱柏翰(Po-Han Chiu)

指導教授 ： 劉冠妙

中山醫學大學/健康管理學院/應用化學系碩士班/碩士(2012年)

https://doi.org/10.6834/CSMU.2012.00175

摘要

本論文主要分成兩個部分，第一部分是基於葡萄醣胺分子之掌性配位基的合成研究，我們以D-葡萄醣胺與2-溴苯甲醯氯進行醯胺化及羥基的保護得到化合物129，其在四氯化錫的作用下會進行分子內脫水反應得到合環化合物128，之後再進行碳-氮偶合反應即可以得到掌性配位基131。第二部分的重點在於具螯合鋅離子基團之螢光性咪唑衍生物的合成研究，我們將具有雙苯基氨取代之9,10-菲醌149與具有螯合鋅離子基團的醛化合物157進行反應，可以得到螢光性咪唑化合物158。

關鍵字

葡萄醣胺 ； 掌性配位基 ； 咪唑 ； 螯合鋅離子

並列摘要

The thesis is composed of two parts. One is the synthetic study of glucosamine based chiral ligands. D-glucosamine was reacted with 2-bromob- enzoyl chloride followed by protection of the hydroxyl groups to get the amide 129, which cyclized under tin chloride (IV) treatment to afford oxazoline 128. Coupling of the benzyl bromide moiety with amine got the desired glucosamine based chiral chelator. The second part of the thesis is the synthetic study of fluorescent imidazole derivatives with Zn(II) chelating ligand.The diphenylamine substituted 9,10-phenanthren- equinone was reacted with benzaldehyde with a Zn(II) recognition moiety, di-(2-picol- y)amine group, to get the fluorescent imidazole compound 158, but the yield is just 7 %. We will devote our effort to improve the yield, study the photophysical properties and sensing ability of this compound in the future.

並列關鍵字

glucosamine ； chiral ligand ； imidazole ； Zn(II) chelating ligand

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