簡易檢索 / 詳目顯示

研究生: 陳昭樺
CHEN, Chao-Hua
論文名稱: 微波輔助研究碘介導的溴肉桂醛、苯甲醯氰和醋酸銨的三組分反應
Iodine Mediated Three Components Reaction of Bromocinnamaldehyde, Benzoyl Cyanide and Ammonium Acetate in Microwave
指導教授: 姚清發
Yao, Ching-Fa
口試委員: 姚清發
Yao, Ching-Fa
林文偉
Lin, Wen-wei
柳如宗
Liu, Ju-Tsung
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: 142
中文關鍵詞: 微波輔助反應(Z)-6-(2-bromo-2-phenylvinyl)-4-hydroxy-2,4-diphenyl-3-azabicyclo [3.1.0] hex-2-ene-1,5-dicarbonitrile
英文關鍵詞: microwave-assisted reaction, iodine, (Z)-6-(2-bromo-2-phenylvinyl)-4-hydroxy-2,4-diphenyl-3-azabicyclo [3.1.0] hex-2-ene-1 ,5-dicarbonitrile
研究方法: 實驗設計法
DOI URL: http://doi.org/10.6345/NTNU202301274
論文種類: 學術論文
相關次數: 點閱:47下載:0
分享至:
查詢本校圖書館目錄 查詢臺灣博碩士論文知識加值系統 勘誤回報
  • 論文的前半部為前言,主要是透過查詢過去的文獻,介紹3-azabicyclo[3.1.0]hexane 的衍生物作為藥物的研究價值,以及其他團隊的合成方法,並說明研究動機及目標。
    後半部為介紹利用微波反應器在碘的作用下使 (Z)-3-bromo-3-phenylacrylaldehyde、3-oxo-3-phenylpropanenitrile與 Ammonium acetate 形成產物 (Z)-6-(2-bromo-2-phenylvinyl)-4-hydroxy-2,4-diphenyl-3-azabicyclo [3.1.0] hex-2-ene-1,5-dicarbonitrile。以及對 (Z)-3-bromo-3-phenylacrylaldehyde、3-oxo-3-phenylpropanenitrile進行官能基的取代,檢測官能基對反應條件的影響。

    The first half of the thesis is the preface, which mainly introduces the research value of 3-azabicyclo[3.1.0]hexane derivatives as drugs and the synthesis methods of other teams through searching past literature, and explains the research motivation and goals.
    The second half is to introduce the use of microwave reactors to form (Z)-6-(2-bromo-2 -phenylvinyl)-4-hydroxy-2,4-diphenyl-3-azabicyclo [3.1.0] hex-2-ene-1,5-dicarbonitrile, and for (Z)-3-bromo-3-phenylacrylaldehyde, 3- oxo-3-phenylpropanenitrile was used to replace the functional group, and the tolerance of the reaction conditions to the functional group was tested.

    謝誌 i 中文摘要 ii Abstract iii 圖目錄 vi 表目錄 viii 式目錄 ix 第一章、前言 1 1-1、3-azabicyclo[3.1.0]hexane 衍生物介紹 1 1-2、文獻回顧 2 第二章、研究目標 7 第三章、實驗結果與討論 8 3-1、起始物製備 8 3-1-1、3-bromo-3-phenylacrylaldehyde 8 3-1-2、3-oxo-3-phenylpropanenitrile 8 3-2、(Z)-6-(2-bromo-2-phenylvinyl)-4-hydroxy-2,4-diphenyl-3-azabicyclo[3.1.0]hex-2-ene-1,5-dicarbonitrile(4aa) 的合成 9 3-2-1、最佳化條件探討 16 3-2-2、取代基效應探討 21 3-3、反應機構 23 3-4、競爭反應 31 3-4-1、(Z)-2-benzoyl-3-(2-bromo-2-phenylvinyl)-5-phenyl-2,3-dihydrofuran-2,4-dicarbonitrile(6aa) 的反應機構 31 3-4-2、(Z)-2-(2-bromo-2-phenylvinyl)-5-phenyloxazole-4-carbonitrile (7aa)的反應機構 31 第四章、結論 33 第五章、實驗方法 34 6-1、分析儀器及基本實驗操作 34 6-2、實驗步驟 36 參考資料 38 光譜資料 41 光譜附圖 124

    (1) Fritz, S. P.; Matlock, J. V.; McGarrigle, E. M.; Aggarwal, V. K. Efficient synthesis of cyclopropane-fused heterocycles with bromoethylsulfonium salt. Chemistry 2013, 19, 10827-10831.
    (2) Wirth, T.; Schmuck, K.; Tietze, L. F.; Sieber, S. A. Duocarmycin analogues target aldehyde dehydrogenase 1 in lung cancer cells. Angew Chem Int Ed Engl 2012, 51, 2874-2877.
    (3) S Gomi, D. I., H Nakamura, H Naganawa, F Yamashita, K Hotta, S Kondo, Y Okami, H Umezawa, Y Iitaka. Isolation and structure of a new antibiotic, indolizomycin, produced by a strain SK2-52 obtained by interspecies fusion treatment. J. Antibiot 1984, 37, 1491-1494.
    (4) Norris, T.; Braish, T. F.; Butters, M.; DeVries, K. M.; Hawkins, J. M.; Massett, S. S.; Rose, P. R.; Santafianos, D.; Sklavounos, C. Synthesis of trovafloxacin using various (1α,5α,6α)-3-azabicyclo[3.1.0]hexane derivatives. Journal of the Chemical Society, Perkin Transactions 1 2000, 1615-1622.
    (5) F. George Njoroge, K. X. C., Neng-Yang Shih, and John J. Piwinski. Challenges in Modern Drug Discovery: A Case Study of Boceprevir, an HCV Protease Inhibitor for the Treatment of Hepatitis C Virus Infection. Acc. Chem. Res. 2008, 41, 50–59.
    (6) Feng Xu, J. A. M., Bryon Simmons, Edward Corley, Kenneth Fitch, Sandor Karady, and David Tschaen. Stereocontrolled Synthesis of Trisubstituted Cyclopropanes:  Expedient, Atom-Economical, Asymmetric Syntheses of (+)-Bicifadine and DOV21947. Org. Lett. 2006, 8, 3885–3888.
    (7) D D Schoepp 1, B. G. J., R A Wright, C R Salhoff, N G Mayne, S Wu, S L Cockerman, J P Burnett, R Belegaje, D Bleakman, J A Monn. LY354740 is a Potent and Highly Selective Group II Metabotropic Glutamate Receptor Agonist in Cells Expressing Human Glutamate Receptors. Neuropharmacology 1997, 36, 1-11.
    (8) Kaur, K.; Aeron, S.; Bruhaspathy, M.; Shetty, S. J.; Gupta, S.; Hegde, L. H.; Silamkoti, A. D.; Mehta, A.; Chugh, A.; Gupta, J. B.; et al. Design, synthesis and activity of novel derivatives of oxybutynin and tolterodine. Bioorg Med Chem Lett 2005, 15, 2093-2096.
    (9) Ren, X.; Chandgude, A. L.; Fasan, R. Highly Stereoselective Synthesis of Fused Cyclopropane-gamma-Lactams via Biocatalytic Iron-Catalyzed Intramolecular Cyclopropanation. ACS Catal 2020, 10, 2308-2313.
    (10) Jing, C.; Jones, B. T.; Adams, R. J.; Bower, J. F. Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp(3))-H Functionalization Cascades. J Am Chem Soc 2022, 144, 16749-16754.
    (11) Richter, M. J. R.; Zecri, F. J.; Briner, K.; Schreiber, S. L. Modular Synthesis of Cyclopropane-Fused N-Heterocycles Enabled by Underexplored Diazo Reagents. Angew Chem Int Ed Engl 2022, 61, e202203221.
    (12) Kim, B. R.; Sung, G. H.; Ryu, K. E.; Lee, S. G.; Yoon, H. J.; Shin, D. S.; Yoon, Y. J. Direct synthesis of pyrazoles from esters using tert-butoxide-assisted C-(C=O) coupling. Chem Commun (Camb) 2015, 51, 9201-9204.

    無法下載圖示 電子全文延後公開
    2028/08/07
    QR CODE