迦瑪環丁內醯胺與環丁內酯骨架分子合成與應用探討

Abstract

迦瑪環丁内醯胺與環丁内酯是相當多天然物結構中的核心骨架，並且是一些藥用化

合物的核心結構。合成該兩種迦瑪環丁内醯胺與環丁内酯的方法多樣。在多種核心合

成方法中，透過一鍋化多組成的反應有節省實驗步驟，並且可有效率的獲得具多樣修

飾官能團的迦瑪環丁内醯胺與環丁内酯。最近，我們發表了一篇以三組成反應，採用

了不尋常的烯炔當做阿爾發麥可反應接受體，並正確的以X-射線繞射解析反應的環丁

内酯產物，建立了三級膦與炔的反麥可反應。

為了延伸我們所建立的阿爾發麥可反應的新反應合成技術，以應用於建構其它相關

的分子結構，及找出所建立環丁内酯架構的應用，我們將嘗試將此一鍋化三組成反應

進行環丁内醯胺的合成。在此計畫書的工作，我們也將嘗試環丁内酯架構與化學感測

做連結。我們設計了以環丁内醯胺與環丁内酯為核心架構，並搭配適合的螯合基進行

化學感測研究的探討。我們將以紫外可見光及螢光光譜分析，研究預設合成分子的光

物理性質，並篩選它們與金屬離子鍵結可行性。

-Lactam and -lactone moieties are important structural motives in many natural products and they are embraced in a number of pharmaceutical applicable molecules. The synthetic methods used for constructing these two core motives are diverse. The one-pot multi-component reactions (MCRs) are step-economic and highly efficient for synthesis of core lactone and lactam skeletons equipped with multiple modifiable functionalities. Recently, we have reported a three-component reaction (3-CR) using an unusual enyne as an ^^"-Michael (^-Michael) acceptor and unambiguously established an a(5’)-Michael addition of phosphines with an enyne through X-ray diffraction analyses of the isolated lactones products.

Our continuing interests in extending our new methodology through a-Michael reaction for building up other related structures and finding out the applications of the resulting lactones have inspired us to build up lactam core through one-pot three-component reaction (OPTCR). In this proposal, we would like to associate our discovered lactone through one-pot multi-component reaction with chemosensing. We propose to investigate possible lactam and lactone skeletons and bring these molecules with appropriate binding motif for chemosensing. We will study the photophysical properties of proposed molecules resulting from anti-Michael reaction with UV-visible and fluorescent measurements and screen their binding phenomena with metal ions.