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研究生： 陳詠心
Yong-Sin Chen
論文名稱： 有機催化4-嘧啶酮進行Aza-Michael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： 2020
畢業學年度： 108
語文別： 英文
論文頁數： 339
中文關鍵詞： 4-嘧啶酮 、Aza-Michael 加成反應
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    • 本篇以有機掌性催化劑來進行Michael addition 反應，以促進4-嘧啶酮與 α,β 不飽和的Michael acceptor 來進行不對稱1,4 加成反應，期望得到高產率與高選擇性之產物，其中又以辛可寧的方胺衍生物可得到最好的反應性，產率可達99 %，鏡像選擇性可達90 %。

    an enantioselective organocatalytic aza-Michael addition reaction of heterocyclic compounds including 4 -hydroxypyrimidinone to α,β-unsaturated Michael acceptor.This is developed with the help of a bifunctional squaramide catalyst to give the corresponding adducts formed in good to excellent enantioselectivity(up to 90 % ee)

    中文論文摘要 i Abstract ii 目錄 iii 圖目錄 vi 表目錄 viii 附圖目錄 ix 第一章 序論 1 1-1 鏡像異構物 1 1-2 4-嘧啶酮 (4(3H)-Pyrimidinone) 6 1-3 Aza-Michael addition 9 1-3-1 早期以金屬或二級胺進行不對稱 Michael addtion 9 1-3-2 以奎寧的硫脲 (thiourea)衍生物作為催化劑進行不對稱 Michael addtion 11 1-3-3 以辛可寧的方胺 (squaramide)衍生物作為催化劑進行不對稱 Michael addtion 12 1-3-4 以 4-oxo-enoates作為 Michael acceptor進行不對稱 1,4加成反應 13 iv 第二章 第二章 研究動機研究動機 ........................................................................................................................................................................................ 16 第三章 第三章 結果與討論結果與討論 ................................................................................................................................................................................ 17 3-1 Michael donor的探討的探討 ........................................................................................................................................................ 17 3-2 以以ethyl 3-benzoylacrylate作為作為Michael acceptor ................................................................ 20 3-2-1 Michael addition溶劑的篩選溶劑的篩選 .................................................................................................................... 21 3-2-2 Michael addition催化劑的篩選催化劑的篩選 ............................................................................................................ 23 3-2-3 Michael addition溫度與時間的篩選溫度與時間的篩選 ............................................................................................ 25 3-2-4 以不同以不同Michael acceptor合成具有鏡像選擇性產物合成具有鏡像選擇性產物 .......................................... 26 3-2-5 Michael addition 放量實驗的探討放量實驗的探討 .................................................................................................. 31 第四章 第四章 結論結論........................................................................................................................................................................................................ 32 第五章 第五章 實驗部分實驗部分 ........................................................................................................................................................................................ 33 5-1實驗藥品與溶劑實驗藥品與溶劑 ........................................................................................................................................................................ 33 5-2實驗器材與儀器實驗器材與儀器 ........................................................................................................................................................................ 34 5-3 實驗步驟與光譜資訊實驗步驟與光譜資訊 ...................................................................................................................................................... 36 5-3-1 掌性催化劑合成掌性催化劑合成 .......................................................................................................................................................... 36 5-3-2 Michael acceptor 合成合成 ........................................................................................................................................ 47 5-3-3 Aza-Michael addition之產物之產物 .................................................................................................................... 67 v 第六章 第六章 文獻參考文獻參考 ........................................................................................................................................................................................ 98

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