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研究生： 吳昱諄
Yu-Chun Wu
論文名稱： 有機催化 2-吡啶酮與 苯甲醯丙烯酸乙酯進 行具鏡像選擇之加成反應
指導教授： 侯敦仁
Duen-Ren Hou
口試委員:
學位類別： 碩士
Master
系所名稱： 理學院 - 化學學系
Department of Chemistry
論文出版年： 2019
畢業學年度： 107
語文別： 中文
論文頁數： 364
中文關鍵詞： 有機催化 、2-吡啶酮
相關次數： 點閱：10  下載：0 
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    • 以辛可寧衍生出的掌性催化劑促成多種2-吡啶酮與a,b-不飽和酮進行
    不對稱1,4 加成反應，其中以辛可寧的方醯胺衍生物可以得到高產
    率及鏡像選擇性，產率可達98%，鏡像選擇性可達99%。並且應用
    2-吡啶酮與苯甲醯丙烯酸乙酯進行麥可加成反應後的產物，可以合
    成出具有光學活性的人類鼻病毒3C 蛋白酶抑制劑前驅物。

    The enantioselective organocatalytic aza-Michael addition of 2-hydroxypyridines (pyridin-2(1H)-ones) to a,b-unsaturated 1,4-diones to yield chiral N-substituted 2-pyridones is reported. The reactions were optimized by the choice of solvents and screening a series of cinchonine catalysts to achieve good yields and enantioselectivities (up to 98% yield and >99% ee). Finally using Michael product completed the synthesis to precursor of Human Rhinovirus 3C Protease Inhibitors through a series of reaction.

    III 總目錄 中文摘要…………………………………………………………………I 英文摘要………………………………………………………………..II 總目錄…………………………………………………………………..III 圖目錄…………………………………………………………………...V 表目錄………………………………………………………………...VII 附圖目錄……………………………………………………………….. 第一章 序論…………………………………………………………...1 1-1 鏡像異構物…………….…………………..…………………....1 1-2 Aza-Michael addition……….………………..………………..…4 1-3 吡啶酮(2-pyridone)…………….…………….……………........9 第二章 研究動機……………………………………………………...13 第三章 結果與討論…………………………………………………...14 3-1 以trans-1,2-dibenzoylethylene作為Michael acceptor………….14 3-1-1 催化劑的篩選……………………………………………..15 3-1-2 溶劑的篩選………………………………………………..18 3-1-3 合成不同具有鏡像選擇性的Michael adducts……………19 3-2 以ethyl 3-benzoylacrylate作為Michael acceptor………………22 3-2-1 合成不同具有鏡像選擇性的Michael adducts…………….23 3-3 人類鼻病毒蛋白酶的抑制劑(HRV 3CP Inhibitors)合成……...24 3-3-1 HRV 3CP Inhibitors合成策略 ……………………………...24 第四章 結論……………………………………………………………34 第五章 實驗部分………………………………………………………35 5-1 實驗藥品與溶劑…………………………………………...35 5-2 實驗器材與儀器…………………………………..……….36 5-3 實驗步驟與光譜資訊………………………………..…….38 5-3-1 掌性催化劑合成……………………………………….38 5-3-2 2-吡啶酮及Michael accept合成………………………..56 5-3-3 Michael addition 產物 ……………………………….…65 5-3-4 HRV 3CP抑制劑前驅物合成………………………….103 第六章 文獻參考……………………………………………………..111

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