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研究生: 蔣宗彥
Jiang, Zong-Yan
論文名稱: 2-烯丙氧基苯甲醛肟利用MeOI和其分子內環化加成反應合成色烯-異噁唑衍生物
Syntheses of Chromeno-isoxazoles From 2-allyloxybenzaldoximes Using MeOI and Their Intramolecular Cycloaddition
指導教授: 姚清發
Yao, Ching-Fa
口試委員: 林文偉
Lin, Wenwei
柳如宗
Liu, Ju-Tsung
姚清發
Yao, Ching-Fa
口試日期: 2023/07/21
學位類別: 碩士
Master
系所名稱: 化學系
Department of Chemistry
論文出版年: 2023
畢業學年度: 111
語文別: 中文
論文頁數: 51
中文關鍵詞: 異噁唑啉超音波震盪器碘分子分子內[3+2]環化加成反應
英文關鍵詞: isooxazoline, intramolecular [3+2] cycloaddition, ultrasonic cleaner, iodine
研究方法: 實驗設計法
DOI URL: http://doi.org/10.6345/NTNU202301385
論文種類: 學術論文
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  • 本篇論文主要分成了五個章節,分別是前言、實驗目標、實驗結果與討論、結論及實驗步驟。前言介紹異噁唑啉衍生物在有機合成和藥物化學的領域具有重要的發展性及,並且透過查詢近幾年的文獻來回顧有關於異噁唑啉衍生物的合成方法。
    實驗目標及實驗結果與討論是將起始物2-烯丙氧基-3-甲氧基苯甲醛肟,利用超音波震盪器,藉由不同的醇類作為有機溶劑和碘分子進行分子內[3+2]環化加成反應,並以良好的產率成功合成出具有三環骨架結構的產物6-Methoxy-3a, 4-dihydro-3H-chromeno[4,3-c]isoxazole。

    This thesis has five parts including introduction, experimental objectives, experimental results, conclusion, and experimental procedure. The preface introduces the important development of isoxazoline derivatives in the field of organic synthesis and medicinal chemistry, and reviews the synthesis methods of isoxazoline derivatives by searching the literature in recent years.
    Experimental objectives, experimental results and discussion introduce intramolecular [3+2] cycloaddition of 2-allyloxy-3-methoxybenzaldoxime which is starting material by using ultrasonic cleaner and different alcohols as organic solvents and iodine molecules, and successfully synthesized the product 6-Methoxy-3a, 4-dihydro-3H-chromeno[4,3-c]isoxazole which has tricyclic skeleton structure in good yields.

    謝誌 i 中文摘要 ii Abstract iii 1.前言 1 1-1、異噁唑啉(isoxazoline)的介紹 1 1-2、氧化腈的1,3-偶極環加成反應介紹 2 1-3、文獻回顧 3 2、實驗目標 14 3、實驗結果與討論 16 3-1合成6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole的路徑 16 3-2化合物1a最佳化條件篩選 18 3-3合成不同取代基 25 3-4 反應機構探討 29 4、結論 31 5、實驗方法 32 5-1、分析儀器及基本實驗操作 32 5-2、實驗步驟 34 5-2-1、2-烯丙氧基苯甲醛的製備 34 5-2-2、2-烯丙氧基苯甲醛肟的製備 35 5-2-3、3a,4-dihydro-3H-chromeno[4,3-c]isoxazole的製備 36 6.參考文獻 37 附件一、光譜資料 39 附件二、光譜附圖 43

    1. J. I Andres, J Alc ´ azar, J. M. Alonso, ´ R. M. Alvarez, M. H. Bakker, I Biesmans, J. M. Cid, A. I. D. Lucas, W. Drinkenburg, J Fernandez, L. M. Font, L. Iturrino, X. Langlois, ´ I. Lenaerts, S. Martı’nez, A. A. Megens, J Pastor, S. Pullan and T. Steckler, Bioorg. Med. Chem., 2007, 15, 3649
    2. James W. Shearman, Rebecca M. Myers, James D. Brenton, Steven V. Ley , Org. Biomol. Chem. 2011, 9, 62
    3. Beugnet F, deVos C, Liebenberg J, Halos L, Fourie J. Afoxolaner against fleas: immediate efficacy and resultant mortality after short exposure on dogs. Parasite. 2014, 21, 42
    4. I. Filali, J. Bouajila, M. Znati, F. Bousejra-El Garah, H. Ben Jannet, J. Enzyme. Inhib. Med. Chem. 2015, 30, 371-376
    5. Easton, C. J.; Hughes, C. M. M.; Savage, G. P.; Simpson, G. W. Adv. Heterocycl. Chem. 1994, 60, 261
    6. Huisgen, Rolf (October 1963). "1,3-Dipolar Cycloadditions. Past and Future". Angewandte Chemie International Edition in English. 2 (10): 565–598.
    7. Radhakrishna, A. S.; Sivaprakash, K.; Singh, B. B. Synth. Commun. 1991, 21, 1625
    8. Das, B.; Holla, H.; Mahender, G.; Banerjee, J.; Reddy, M. R. Tetrahedron Lett. 2004, 45, 7347
    9. Das, B.; Holla, H.; Mahender, G.; Venkateswarlu, K.; Bandgar, B. P. Synthesis 2005, 1572
    10. Chatterjee, N.; Pandit, P.; Halder, S.; Patra, A.; Maiti, D. K. J. Org. Chem. 2008, 73, 7775
    11. Raihan, M. J.; Kavala, V.; Kuo, C.-W.; Raju, R.; Yao, C.-F. Green Chem. 2010, 12, 1090
    12. Minakata, S.; Okumura, S.; Nagamachi, T.; Takeda, Y. Org. Lett. 2011, 13, 2966,
    13. Yoshimura, A.; Middleton, K. R.; Todora, A. D.; Kastern, B. J.; Koski, S. R.; Maskaev, A. V.; Zhdankin, V. V. Org. Lett. 2013, 15, 4010
    14. Yoshimura, A.; Zhu, C.; Middleton, K. R.; Todora, A. D.; Kastern, B. J.; Maskaev, A. V.; Zhdankin, V. V. Chem. Commun. 2013, 49, 4800
    15. Han, L.; Zhang, B.; Xiang, C.; Yan, J. Synthesis 2014, 46, 503

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