簡易檢索 / 詳目顯示
| 研究生： |
吳倩茹 Wu, Chien-Ju |
|---|---|
| 論文名稱： |
一鍋化合成硝基環丙烷之研究 One-Pot Synthesis of Nitrocyclopropane |
| 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： | 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： | 72 |
| 中文關鍵詞： | 硝基環丙烷 |
| 英文關鍵詞： | nitrocyclopropane |
| 研究方法: | 實驗設計法 |
| DOI URL： | http://doi.org/10.6345/NTNU202200955 |
| 論文種類： | 學術論文 |
| 相關次數： | 點閱：62 下載：7 |
| 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 |
硝基環丙烷不只是可以合成複雜有機分子的前驅物，也是許多具有生物活性的天然物或非天然物的基礎結構。我們的合成策略是使用丙二酸二乙酯(Diethyl malonate)和硝基苯乙烯(β-Nitrostyrene)作為起始物，先加入鹼進行Michael加成反應後，再加入N-溴代丁二醯亞胺(N-Bromosuccinimide, NBS)作為溴化試劑生成含有溴的中間體，最後利用鹼進行分子內環化反應便可得到硝基環丙烷產物。而我們可以藉由使用不同的硝基烯烴作為起始物以合成產率不錯的一系列硝基環丙烷產物。
Nitrocyclopropane is not only a precursor for the synthesis of complex organic molecules, but also the basic structure of many biologically active natural or non-natural substances. This developed synthetic process involves the Michael addition of diethyl malonate to various nitroolefins, followed by bromination with N-bromosuccinimide to generate a bromine-containing intermediate. Then, the brominated adduct is added with a base for intramolecular cyclization to obtain the highly functionalized nitrocyclopropanes product in moderate to good yields. We have pioneered a high-efficiency method for synthesizing nitrocyclopropane, which is easy to operate, and the reagents used in the process are all commercially available and cheap reagents.
(1) Xuan, Y. N.; Nie, S. Z.; Dong, L. T.; Zhang, J. M.; Yan, M. Organic Letters 2009, 11 (7), 1583-1586.
(2) Zlatopolskiy, B. D.; Loscha, K.; Alvermann, P.; Kozhushkov, S. I.; Nikolaev, S. V.; Zeeck, A.; de Meijere, A. Chemistry 2004, 10 (19), 4708-4717.
(3) Asai, A.; Hasegawa, A.; Ochiai, K.; Yamashita, Y.; Mizukami, T. Journal of Antibiot (Tokyo) 2000, 53 (1), 81-83.
(4) Gootz, T. D.; Brighty, K. E. Medicinal Research Reviews 1996, 16 (5), 433-486.
(5) Hass, H.; Shechter, H. Journal of the American Chemical Society 1953, 75 (6), 1382-1384.
(6) A S Sopova, V V Perekalin, O I Yurchenko, G M Arnautova Russian Journal of Organic Chemistry 5 868 (1969)
(7) Kocór, M.; Kroszczyński, W. Synthesis 1976, 1976 (12), 813-814.
(8)Kuwajima, I.; Ando, R.; Sugawara, T. Tetrahedron Letters 1983, 24 (41), 4429-4432.
(9) Zindel, J.; de Meijere, A. The Journal of Organic Chemistry 1995, 60 (10), 2968-2973.
(10) TF, B. Castaldi M. Chan S. Fox DE. Keltonic T. McGarry J. Hawkins JM. Norris T. Rose PR. Sieser JE. Sitter BJ. Watson H. Synlett 1996, 1100.
(11) Arai, S.; Nakayama, K.; Ishida, T.; Shioiri, T. Tetrahedron Letters 1999, 40 (22), 4215-4218.
(12) Maestro, M. C.; Barquilla, M. C.; Martı́n, M. R. Tetrahedron: Asymmetry 1999, 10 (18), 3593-3599.
(13) Norris, T.; Braish, T. F.; Butters, M.; DeVries, K. M.; Hawkins, J. M.; Massett, S. S.; Rose, P. R.; Santafianos, D.; Sklavounos, C. Journal of the Chemical Society, Perkin Transactions 1 2000, (10), 1615-1622.
(14) Ivanova, O.; Yashin, N.; Averina, E.; Grishin, Y. K.; Kuznetsova, T.; Zefirov, N. Russian Chemical Bulletin 2001, 50 (11), 2101-2105.
(15)Hansen, H. M.; Longbottom, D. A.; Ley, S. V. Chemical Communications 2006, (46), 4838-4840.
(16) McCooey, S. H.; McCabe, T.; Connon, S. J. The Journal of Organic Chemistry 2006, 71 (19), 7494-7497.
(17) Anisimova, N.; Makarova, N.; Berkova, G.; Berestovitskaya, V. Russian Journal of General Chemistry 2006, 76 (10), 1545-1549.
(18) Schollkopf, U.; Tonne, P. Annalen der Chemie-Justus Liebig 1971, 753, 135.
(19) O'Bannon, P.; Dailey, W. P. The Journal of Organic Chemistry 1989, 54 (13), 3096-3101.
(20) Galley, G.; Hübner, J.; Anklam, S.; Jones, P. G.; Pätzel, M. Tetrahedron Letters 1996, 37 (35), 6307-6310.
