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

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吳昱諄(Yu-Chun Wu) 查詢紙本館藏

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化學學系

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

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摘要(中)

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。

摘要(英)

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.

關鍵字(中)

★ 有機催化
★ 2-吡啶酮

關鍵字(英)

論文目次

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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指導教授

侯敦仁(Duen-Ren Hou)

審核日期

2019-8-22

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