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研究生: 李昀靜
Li, Yun-Ching
論文名稱: (Z)-3-(2-硝基苯亞基)-2,3-二氫-4氫-苯并[b]氧㖕-4-酮衍生物的合成及其應用在(Z)-6氫-苯并[7,8]氧㖕并[4,3-b]喹啉衍生物
Preparation of (Z)-3-(2-nitrobenzylidene)-2,3-dihydro-4H-benzo[b]oxocin-4-one Derivatives and its Application to Synthesis of (Z)-6H-benzo[7,8]oxocino[4,3-b]quinoline Derivatives
指導教授: 姚清發
Yao, Ching-Fa
口試委員: 林文偉
Lin, Wen-Wei
柳如宗
Liu, Ru-Zong
姚清發
Yao, Ching-Fa
口試日期: 2022/07/20
學位類別: 碩士
Master
系所名稱: 化學系
Department of Chemistry
論文出版年: 2022
畢業學年度: 110
語文別: 中文
論文頁數: 107
中文關鍵詞: 森田-貝里斯-希爾曼反應
英文關鍵詞: Morita-Baylis-Hillman reaction
研究方法: 實驗設計法
DOI URL: http://doi.org/10.6345/NTNU202201036
論文種類: 學術論文
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  • 本篇研究主要為論述(Z)-6氫-苯並[7,8]氧㖕並[4,3-b]喹啉衍生物的合成,將其分為兩部分。第一部分是介紹喹啉及氧㖕的性質與合成方法,並藉由文獻資料構建合成策略進而產生研究目標。
    第二部分則將此合成策略分成五個步驟,首先具有不同取代基的鄰硝基苯甲醛1與丁烯酮2進行森田-貝里斯-希爾曼反應生成化合物3後,再利用乙醯氯生成化合物4,接著與不同取代基的水楊醛5進行SN2反應生成化合物6,而後經由羥醛縮合反應形成具有八圓環的化合物7,最終,透過進行硝基的還原及分子內環化反應來得到(Z)-6氫-苯並[7,8]氧㖕並[4,3-b]喹啉衍生物8。

    This research mainly discusses the synthesis of (Z)-6H-benzo[7,8] oxocino[4,3-b]quinoline derivatives, which is divided into two parts. The first part is to introduce the properties and synthetic methods of quinolines and oxocines. In addition, the relevant literature on the synthesis strategy are described.
    In the second part, the synthetic strategy of the preparation of oxocine derivatives consists of five steps. First, 2-nitrobenzaldehyde with different substituents 1 undergo the Morita-Baylis-Hillman reaction with butenones 2 to provide the compounds 3 which are further converted into the compound 4 after the treatment of acetyl chloride. After that, the compounds 4 undergoes the SN2 reaction with salicylaldehydes with different substituents 5 to afford the compounds 6. Furthermore, the compounds 7 with an eight-membered ring are synthesized via the intramolecular aldol condensation reactions of 6. Ultimately, the (Z)-6H-benzo[7,8]oxocino[4,3-b]quinoline derivatives 8 from 7 via the nitro group reduction are obtained by the reduction of the nitro-group and the intramolecular cyclization reaction.

    摘要 I Abstract II 1-1 、前言 1 1-1-1 喹啉(Quinoline)衍生物的介紹 1 1-1-2 氧㖕(Oxocine)衍生物的介紹 2 1-2 研究目標 6 1-3 實驗結果與討論 8 1-3-1 Baylis-Hillman合成不同取代基的產物 8 1-3-2 化合物3與乙醯氯由SN2反應進行氯化合成化合4 10 1-3-3 化合物4與不同取代基的水楊醛5反應製備化合6 12 1-3-4 八元環氧㖕(Oxocine)的合成 17 1-3-5 合成不同取代基的(Z)-6氫-苯並[7,8]氧㖕並[4,3-b]喹啉 20 1-4 結論 23 1-5 實驗方法 24 1-5-1 一般實驗方法 24 1-5-2 實驗步驟 26 1-6 參考文獻 31 1-7 光譜資料 32 1-8 光譜附圖 47

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