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| 研究生： |
陳楷涵 Chen, Kai-Han |
|---|---|
| 論文名稱： |
利用新開發的香豆素衍生物經由 (3+2) 合環合成具有高鏡像選擇性的五碳環化合物 Highly Enantioselective Synthesis of Cyclopentane from Newly Developed Coumarin Derivatives by Organocatalytic Asymmetric (3+2) Cyclization |
| 指導教授： |
林文偉
Lin, Wen-Wei |
| 學位類別： |
碩士 Master |
| 系所名稱： |
化學系 Department of Chemistry |
| 論文出版年： | 2017 |
| 畢業學年度： | 105 |
| 語文別： | 中文 |
| 論文頁數： | 315 |
| 中文關鍵詞： | 有機不對稱催化 、高掌性香豆素五環結構 |
| 英文關鍵詞： | Organocatalytic Asymmetric, Highly Enantioselective Synthesis of Cyclopentane |
| DOI URL： | https://doi.org/10.6345/NTNU202202818 |
| 論文種類： | 學術論文 |
| 相關次數： | 點閱：124 下載：2 |
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由於香豆素及其衍生物在天然界中具有廣大的生物活性，為一個重要的天然物，因此對於如何在香豆素的類苯環系統上進行加成是一個很重要的課題，過往利用有機不對稱催化反應在香豆素上建構的結構多為具有雜原子的五員環，而今，我們利用新開發的香豆素衍生物作為反應物，能夠成功的在其上建構以往較為困難的五碳環結構，並經由中間體探討其反應機構。
第二部分，在有機反應中複雜化合物的合成通常是需要經由多步反應步驟去建構合成的，但由於多步驟反應容易造成資源的浪費，故研究經由串聯反應建構化合物成為一個重要的課題，本部分著重在於串聯反應起始物的開發構想與測試結果。
Coumarin derivatives have the large biological activity, and in nature are also important natural product, therefore, how to make the addition on coumarin derivatives becomes a very important issue. In the past, we mostly construct five heteroatomed ring on the coumarin in asymmetric-organocatalyzed reaction. Nowadays, we use the newly developed coumarin derivatives as the substrates, and develope the great strategy to establish the five-carbon ring on the coumarin derivatives, and use the intermediates to figure out this reaction mechanism.
In the second part, the synthesis of complex compounds in organic reactions usually requires the construction of the steps via the multi-step reaction step. However, due to the fact that the multi-step reaction is liable to the waste of resources, so research has become an important subject through the domimo reaction. This part focusing on the development of serial reaction initiation ideas and test results.
1-6 參考文獻
1. Ng, D.; Yang, Z.; Garcia-Garibay, M. A. Org. Lett., 2004, 6, 645.
2.. Li, H.; Wu, J. Synthesis, 2015, 47, 22.
3. Lange, G. L.; Gottardo, C. Tetrahedron. Lett., 1994, 35, 8513.
4. Harrison, T. J.; Dake, G. R. Org. Lett., 2004, 6, 5023.
5. Koteswar Rao, Y.; Nagarajan, M. Tetrahedron. Lett., 1988, 29, 107.
6. Klein, H.; Mayr, H. Angew. Chem. Int. Ed., 1981, 20, 1027.
7. Boger, D. L.; Wysocki, R. J. J. Org. Chem., 1988, 53, 3408.
8. Tokuyama, H.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc., 1992, 114, 5523.
9. Trost, B. M.; Kuo, G. H.; Benneche, T. J. Am. Chem Soc., 1988, 110, 621.
10. Wang, Y.; Yu, Z.-H.; Zheng, H.-F.; Shi, D.-Q. Org. Biomol. Chem., 2012, 10, 7739.
11. Fedorov, A. Yu. et al. Chem. Heterocycl. Comp., 2012, 48, 166
12. Chang, G.-H.; Wang, C.-Y.; Madhusudhan Reddy, G.; Tsai, Y.-L.; Lin, W. J. Org. Chem., 2016, 81, 10071.
2-6 參考文獻
1.Tietze, L. F. Chem. Rev., 1996, 96, 115.
2. Rendler, S.; MacMillan, D. W. C. J. Am. Chem. Soc., 2010, 132, 5027.
3. Volla, C. M. R.; Atodiresei, I.; Rueping, M. Chem. Rev., 2014, 114, 2390.
4.a) Frédérick, R.; Dumont, W.; Ooms, F.; Aschenbach, L.; Van der Schyf, C. J.; Castagnoli, N.; Wouters, J.; Krief, A. J. Med. Chem., 2006, 49, 3743.b) Nugiel, D. A.; Etzkorn, A.-M.; Vidwans, A.; Benfield, P. A.; Boisclair, M.; Burton, C. R.; Cox, S.; Czerniak, P. M.; Doleniak, D.; Seitz, S. P. J. Med. Chem., 2001, 44, 1334.
5. Shirini, F.; Akbari-Dadamahaleh, S.; Mohammad-Khah, A. Chinese. J. Catal., 2013, 34, 2200.
6. El-Zohry, M.F.,* Elossaily, Y.A., Mohamed, T.A. and Hussein, E.M. Heterocycles 2008,75,955
7. Li, Y.-L.; Wang, K.; Zhao, B.; Jiang, Q.-S.; Du, B.-X.; Chen, C.-F. Res. Chem. Intermed., 2015, 41, 5149.
8. Möhlmann, L.; Chang, G.-H.; Madhusudhan Reddy, G.; Lee, C.-J.; Lin, W. Org. Lett., 2016, 18, 688.
9. Yang, S.-M.; Reddy, G. M.; Wang, T.-P.; Yeh, Y.-S.; Wang, M.; Lin, W. Chem. Commun., 2017, 53, 7649.
