簡易檢索 / 詳目顯示

回結果列表
研究生： 丁奕晴
Ting, Yi-Ching
論文名稱： 銠金屬(I)/掌性雙烯配體催化芳香基硼鹽對喹啉鹽進行不對稱芳基化反應
Enantioselective Rhodium-Catalyzed Arylation of Quinolinium Salts
指導教授： 吳學亮
Wu, Hsyueh-Liang
學位類別： 碩士
Master
系所名稱： 化學系
Department of Chemistry
論文出版年： 2018
畢業學年度： 106
語文別： 中文
論文頁數： 284
中文關鍵詞： 銠金屬 、掌性雙烯配體 、芳香基硼鹽 、喹啉鹽 、不對稱芳基化反應
英文關鍵詞： Quinolinium Salts
DOI URL： http://doi.org/10.6345/THE.NTNU.DC.070.2018.B05
論文種類： 學術論文
相關次數： 點閱：77  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

    • 本論文是在探討以 3 mol %一價銠金屬及本實驗室所開發的雙環[2.2.1]樟腦型醯胺類雙烯配基 L7j 或雙環[2.2.1]樟腦型雙烯配基 L6i所形成的錯合物，以 1,4-二噁烷作為溶劑並在 100°C 下進行，催化一系列芳香基硼鹽對喹啉進行不對稱 1,2-加成反應，得到一系列以 氮-苄基-2-苯基-1,2-二氫喹啉化合物， 有高達 90%的產率以及 92%的鏡像超越值。

    In this thesis, enantioselective arylation of N-Benzyl quinolinium salts is described. In the presence of 3 mol % ofthe catalyst generated in situ from [RhCl(C2H4)2]2 and chiral bicycloheptadiene ligand L7j or L6i, reaction of various quinolinium tetraarylborates gives rise to the corresponding enantio-enriched N-benzoy-2-aryl-1,2-dihydroquinolines in up to 90% yield with up to 92% ee at 100°C in dioxane.

    中文摘要 Abstract 表目錄 圖目錄 縮寫對照表 第一章 緒論 1 第二章 文獻回顧 19 第三章 掌性配基合成方法 26 I. 雙環[2.2.1]樟腦型雙烯配基 26 II. 雙環[2.2.1]樟腦型醯胺類雙烯配基 27 第四章 實驗結果與討論 30 I. 親和性試劑對反應性的探討 30 II. 掌性配基上官能基效應的探討 31 III. 喹啉上的保護基對反應性的探討 34 IV. 掌性配基上氢鍵效應的探討 37 V. 溶劑對反應性的探討 40 VI. 溫度對反應性的探討 41 VII. 催化劑添加量對反應性的探討 42 VIII.喹啉上的保護基對反應性的探討 43 IX. 最佳化催化條件 45 X. 親核性試劑上不同官能基對反應性的影響 48 XI. 親電子性試劑上不同官能基對反應性的影響 51 XII. 絕對立體化學探討 54 第五章 合成應用 56 第六章 結論 57 第七章 實驗部分 58 I. 分析儀器 58 II. 芳香硼鹽的製備(I) 61 III. 芳香硼鹽的製備(II) 62 IV. 喹啉的製備 63 V. 喹啉鹽的製備(I) 64 VI. 喹啉鹽的製備(I) 65 VII. 銠金屬催化反應製備 93 第八章 參考文獻 138 附錄 143 I. 起始物核磁共振光譜圖 144 II. 產物核磁共振光譜圖 197 III. 掌性配基核磁共振光譜圖 254

    1. Vellaisamy Sridharan； Padmakar A. Suryavanshi； J. Carlos Menéndez.Chem. Rev. 2011, 111, 7157–7259.
    2. Keith M. Witherup； Richard W. Ransom； Amy C. Graham,AuroraM. Bernard； Michael J. Salvatore； William C. Lumma； Paul S.Anderson； Steven M. Pitzenberger； Sandor L. Varga. J. Am. Chem.Soc. 1995, 117, 6682-6685.
    3. Jacquemond-Collet； Benoit-Vical F； Valentin A； Stanislas E； MalliéM； Fourasté. Planta Med. 2002, 1, 9.
    4. Joseph P. Michael. Nat. Prod. Rep., 2001, 18, 543–559.
    5. Bartholomeu A. Barros-Filho； Fátima M. Nunes； Maria C.F. deOliveira； Jair Mafezoli； Manoel Andrade-Neto； Edilberto R. Silveira；JoséR. Pirani. Biochemical Systematics and Ecology, 2004, 32, 817–821.
    6. Fernando D. Suvire； Maximiliano Sortino； Vladimir V. Kouznetsov；Leonor Y. Vargas M； Susana A. Zacchino； Uriel Mora Cruzb； RicardoD. Enriza. Bioorg. Med. Chem. 2006, 14, 1851 –1862.
    7. Atul R. Gholap； Kiran S. Toti； Fazal Shirazi； Ratna Kumari； ManojKumar Bhat； Mukund V. Deshpande； Kumar V. Srinivasana. Bioorg.Med. Chem. 2007, 15, 6705–6715.
    8. Kirandeep Kaur； Meenakshi Jain； Ravi P. Reddy； Rahul Jain. Eur JMed Chem. 2010, 45, 3245–3264.
    9. Charles Z. Ding, John T. Hunt, Carol Ricca, Veeraswamy Manne.Bioorg. Med. Chem. Lett. 2000, 10, 273–275.
    10. Jing-Ping Liou, Zi-Yi Wu, Ching-Chuan Kuo, Chi-Yen Chang, Pei-YiLu, Chi-Ming Chen, Hsing-Pang Hsieh, Jang-Yang Chang. J. Med.Chem. 2008, 51, 4351 –4355.11. K. Nagaiah, A. Venkatesham, R. Srinivasa Rao, V. Saddanapu, J. S.Yadav, S. J. Basha, A. V. S. Sarma, B. Sridhar, A. Addlagatta. Bioorg.
    Med. Chem. Lett. 2010, 20, 3259–3264.
    12. Marion Raoul, Corinne Schaeffer, Stéphane Léonce, Alain Pierré,Ghanem Atassi, Reynald Hocquemillera, Guy Lewina. Bioorg. Med.Chem. Lett. 2001, 11, 79–81.
    13. Michel C. Maillard, Michael E. Perlman, Oved Amitay, DeborahBaxter, David Berlove, Sonia Connaughton, James B. Fischer, JunQing Guo, Lain-Yen Hu, Robert N. McBurney, Peter I. Nagy,Katragadda Subbarao, Elizabeth A. Yost, Lu Zhang, Graham J. Durant.J. Med. Chem. 1998, 41, 3048-3061.
    14. Shoji Fukumoto, Eiko Imamiya, Keiji Kusumoto, Shuji Fujiwara,Toshifumi Watanabe, and Mitsuru Shiraishi, J. Med. Chem. 2002, 45,3009-3021.
    15. Vijay K. Gore, Vu V. Ma, Ruoyuan Yin, Joe Ligutti , David Immke ,Elizabeth M. Dohertya, Mark H. Norman , Bioorg. Med. Chem. Lett.2010, 20, 3573–3578.
    16. Elizabeth M. Doherty, Christopher Fotsch, Yunxin Bo, Partha P.Chakrabarti, Ning Chen, Narender Gavva, Nianhe Han, MichaelG. Kelly, John Kincaid, Lana Klionsky, Qingyian Liu, Vassil I.Ognyanov, Rami Tamir, Xianghong Wang, Jiawang Zhu, Mark H.Norman, and James J. S. Treanor. J. Med. Chem. 2005, 48, 71 -90.17. Adam Banks, Gary F. Breen, Darren Caine, John S. Carey, ChristopherDrake, Michael A. Forth Asa Gladwin, Simone Guelfi, Jerome F.Hayes, Paolo Maragni, David O. Morgan, Paul Oxley, Alcide Perboni,Matthew E. Popkin, Fiona Rawlinson, Guillaume Roux. OrganicProcess Research & Development, 2009, 13, 1130–1140.
    18. Jiwen Liu, Yingcai Wang, Ying Sun, Derek Marshall, Shichang Miao,George Tonn, Penny Anders,Joel Tocker, H. Lucy Tang, Julio Medina,Bioorg. Med. Chem. Lett. 2009, 19, 6840–6844.
    19. Owen B. Wallace, Kenneth S. Lauwers, Scott A. Jones and Jeffrey A.Dodge, Bioorg. Med. Chem. Lett., 2003, 13, 1907–1910.
    20. Margaret E. Brousseau, Ph.D., Ernst J. Schaefer, M.D., Megan L.Wolfe, B.S., LeAnne T. Bloedon, M.S., R.D., Andres G. Digenio,M.D., Ph.D., Ronald W. Clark, M.S., James P. Mancuso, Ph.D., DanielJ. Rader, M.D. N Engl J Med. 2004, 350, 1505-1515.
    21. Gee-Hong Kuo, Thomas Rano, Patricia Pelton, Keith T. Demarest,Alan C. Gibbs, William V. Murray, Bruce P. Damiano, andMargery A.Connelly. Gee-Hong Kuo, Thomas Rano, Patricia Pelton, Keith T.Demarest, Alan C. Gibbs, William V. Murray, Bruce P. Damiano,Margery A. Connelly. J. Med. Chem. 2009, 52, 1768–1772.
    22. Thomas A. Rano , Ellen Sieber-McMaster, Patricia D. Pelton, MariaYang, Keith T. Demarest, Gee-Hong Kuo. Bioorg. Med. Chem. Lett.,2009, 19, 2456–2460.23. Shigeki Hibi, Kouichi Kikuchi, Hiroyuki Yoshimura, Mitsuo Nagai,Kenji Tai, and Takayuki Hida. J. Med. Chem. 1998, 41, 3245-3252.
    24. Cécile Parmenon a , Jérôme Guillard , Daniel-Henri Caignard ,Nathalie Hennuyer , Bart Staels , Valérie Audinot-Bouchez , JeanAlbert Boutin , Catherine Dacquet , Alain Ktorza , Marie-ClaudeViaud-Massuard, Bioorg. Med. Chem. Lett. 2009, 19, 2683–2687.
    25. HyeSung Kim, HyoJin Gim, Mihi Yang, Jae-Ha Ryu, and Raok Jeon.HETEROCYCLES, Vol. 71, 10, 2007.
    26. Howard C. Smith, Caitlin K. Cavanaugh, Jennifer L. Friz, Christine S.Thompson, Jessica A. Saggers, Enrique L. Michelotti, Javier Garciab,Colin M. Ticea. Bioorg. Med. Chem. Lett. 2003, 13, 1943–1946.
    27. F Santangelo, C Casagrande, G Miragoli, V Vecchietti. Eur J MedChem, 1994, 29,877-882.
    28. Lien Ai Nguyen, Hua He, Chuong Pham-Huy. Int J Biomed Sci. 2006,2, 85–100.
    29. Ping Tian, Han-Qing Dong, Guo-Qiang Lin. ACS Catal. 2012, 2, 95−119.
    30. De-Yang Zhang, Duo-Sheng Wang, Min-Can Wang, Chang-Bin Yu,Kai Gao, Yong-Gui Zhou. Synthesis, 2011, 17, 2796–2802.
    31. Jialin Wen, Renchang Tan, Shaodong Liu, Qingyang Zhao, XumuZhang. Chem. Sci. 2016, 7, 3047–3051.
    32. Christian Nadeau, Sara Aly, Kevin Belyk. J. Am. Chem. Soc. 2011,133, 2878–2880.
    33. Yan Wang, Yunlong Liu, Dongdong Zhang, Hao Wei, Min Shi, Feijun Wang. Angew. Chem. Int. Ed. 2016, 55, 3776 –3780.34. Wei-Ting Wei, Jiann-Yih Yeh, Ting-Shen Kuo, Hsyueh-Liang Wu.
    Chem. Eur. J. 2011, 17, 11405 – 11409.
    35. Jin-Fong Syu, Huang-Ying Lin, Yu-Yi Cheng, Yao-Chu Tsai, Yi Ching Ting, Ting-Shen Kuo, Damodar Janmanchi, Ping-Yu Wu,
    Julian P. Henschke, Hsyueh-Liang Wu. Chem. Eur. J. 2017, 23, 14515– 14522.
    36. Dhananjayan Vasu, Hideki Yorimitsu, Atsuhiro Osuka. Angew. Chem.Int. Ed. 2015, 54, 7162 –7166.
    37. Malcolm P. Roberts, Dolores Clavell-Grunbaum, Herbert L. Strauss.J. Chem. Phys. 1987, 87, 6393-6405.
    38. Jixing Li, Jinlong Zhang, Huameng Yang, and Gaoxi Jiang. J. Org.Chem. 2017, 82, 3284 −3290.

    無法下載圖示 本全文未授權公開
    QR CODE