以有機催化2-吡啶酮具鏡像選擇性共軛加成反應之探討

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研究生：	鐘毅 Yi Jhong
論文名稱：	以有機催化2-吡啶酮具鏡像選擇性共軛加成反應之探討
指導教授：	侯敦仁
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：	2017
畢業學年度：	105
語文別：	中文
論文頁數：	272
中文關鍵詞：	以有機催化2-吡啶酮具鏡像選擇性共軛加成反應之探討
相關次數：	點閱：20 下載：0
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本篇是以有機鹼做為催化劑，藉由合成多種辛可寧衍生出的掌性催化劑來激發2-吡啶酮進行不對稱1,4加成到Michael acceptor上，期望可以得到高產率及鏡像選擇性，其中以辛可寧錠的方醯胺衍生物可以帶來最高的效益，產率可達96%，鏡像選擇性可達93%。

A series of cinchonidine drived catalysts were synthesized from cinchonine . Under the optimal conditions, a cinchonidine-based squaramide was found to be an excellent catalyst for the enantioselective aza-Michael addition of 5-chloro-2-hydroxypyridine with various Michael acceptors. This approach yielded high enantioselectivity (up to 93%) and yield(up to 96%).

中文論文摘要I
AbstractII
總目錄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    2-吡啶酮(2-pyridone) 5
1-3    Aza-Michael addition 8
  1-3-1 以掌性pyrrolidine的衍生物作為催化劑進行不對稱的
        Michael addition 8
   1-3-2以有機酸作為添加劑所進行的不對稱Michael addition 10
   1-3-3以奎寧的硫脲(thiourea)衍生物作為催化劑所進行的不對稱1,4加成反應 12
   1-3-4以1,4-ketoesters作為Michael acceptor所進行的不對稱Michael addition 反應 14
   1-3-5以奎寧的squaramide衍生物作為催化劑進行的Michael addition 17
   1-3-6利用不飽和的1,4雙酮作為Michael acceptor 進行的Michael addition 18
第二章 研究動機 22
第三章 結果與討論 23
   3-1 以dimethyl fumarate作為Michael acceptor 23
   3-2 以Ethyl 3-benzoylacrylate作為Michael acceptor 24
      3-2-1添加劑的篩選 26
      3-2-2 溶劑的篩選 27
      3-2-3催化劑的篩選 29
      3-2-4優化條件的組合 34
      3-2-5降低溫度來提升鏡像選擇性 34
   3-3 以trans-1,2-Dibenzoylethylene作為Michael acceptor 35
      3-3-1催化劑的篩選 37
      3-3-2 溶劑的篩選 38
      3-3-3 降低催化劑的當量數 39
      3-3-4以不同Ethyl 3-benzoylacrylate作為Michael acceptor 40
      3-3-5以2-吡啶酮作為Michael donor 42
第四章 結論 43
第五章 實驗部分 44
   5-1實驗藥品與溶劑 44
   5-2實驗器材與儀器 44
   5-3實驗步驟與光譜資訊 47
      5-3-1掌性催化劑合成 47
      5-3-2反式1,2-二苯酰基乙烯 77
      5-3-3催化反應 87
第六章：參考文獻 105
                                

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