臺灣博碩士論文加值系統

本論文敘述將對-乙烯基酚經由氧化偶合反應(oxidative coupling)製備苯二氫呋喃(dihydrobenzofurans)。利用4-羥基苯甲醛(4-hydroxybenzaldehyde)及其衍生物作為起始原料，分別經由Wittig reaction以及crossed aldol condensation 製備 p-vinylphenols，再利用硝酸鈰銨試劑(cerium(Ⅳ) ammomium nitrate)進行氧化偶合，合成一系列苯二氫呋喃結構之化合物。

In this thesis, an improved method for the preparation of dihydrobenzofurans was described. The starting materials, p-vinylphenols was prepared from the corresponding p-hydroxybenzaldehydes via crossed aldol condensation or Wittig reaction in good yields. The p-vinylphenols were then treated with respectively cerium(Ⅳ) ammomium nitrate to undergo oxidative coupling to give dihydrobenzofurans in few minutes, and in moderated yields.

目錄
中文摘要………………………………………………………1
英文摘要………………………………………………………2
第一章 前言………………………………………………3
第二章 研究動機…………………………………………12
第三章 研究策略與合成設計途徑………………………13
第四章 結果與討論………………………………………14
第五章 實驗部份
一、實驗試劑………………………………………………24
二、溶媒的處理……………………………………………25
三、實驗儀器………………………………………………26
四、實驗步驟及數據分析…………………………………27
參考文獻………………………………………………………41

參考文獻
1.Chang, J. Y.; Chang, C. Y.; Kuo, C. C.; Chen, L. T.; Wein, Y. S. Mol Pharmacol. 2004, 65, 77-84.
2. Snider, B. B.; Han, L.; Xie, C. J. Org. Chem. 1997, 62, 6978
-6984.
3.Wang, E. C.; Wein, Y. S.; Kuo, Y. H. Tetrahedron Lett. 2006, 47, 9195-9197.
4. Bassoli, A.; Gregorio, G. D.; Rindone, B.; Tollari, S. Gazz.
Chim. Ital. 1988, 118, 763-768.
5.Krawczyk, A. R.; Lipkowska, E.; Wrobel, J. T. Collect. Czech. Chem. Commun. 1991, 56, 1147-1150.
6.Chioccara, F.; Poli, S.; Rindone, B.; Pilati, T.; Brunow, G. Acta Chemica Scandinavica, 1993 ,47, 610-616.
7.Iqbal, J.; Bhatia, B.; Nayyar, N. K. Tetrahedron, 1991, 47, 6457-6468.
8. Nair, V.; Mathew, J. J. Chem. Soc. Perkin Trans. I. 1995,
1881-1882.
9. Roy, S. C.; Mandal, P. K. Tetrahedron, 1996, 52, 2193-2198.
10. Nair, V.; Mathew, J.; Prabhakaran, J. Chem. Soc. Rev. 1997, 127-132.
11. Lee, Y. R.; Kim, B. S.; kim, D. H. Tetrahedron, 2000, 56,
8845-8853.
12. Nair, V.; Mathew, J. J. Chem .Soc. Perkin Trans. I. 1995,
187-188.
13. Nair, V.; Mathew, J. Tetrahdron Lett. 1997, 38, 2191-2194.
14. Heiba, E. I.; Dessau, R. M. J. Am. Chem. Soc. 1971, 93,
524-527.
15. Juhasz, L.; Kurti, L.; Antus, S. J. Nat. Prod. 2000, 63, 866- 870.
16. Wallis, A. F. A. Aust. J. Chem. 1973, 26, 1571-1576.
17. Kuo, Y. H.; Wu, C. H. J. Nat. Prod. 1996, 59, 625-628.
18. Kim, S. S.; Jung, H. C. Synthesis, 2003, 14, 2135-2137.
19. Nair, V.; Suja, T. D.; Mohanan, K. Synthesis, 2006, 15, 2531-2534.
20. Paul, S.; Gupta, M. Synthetic Commun. 2005, 35, 213-222.
21. Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002,
124, 6343-6348.
22. Simpson, C. J.; Fitzhenry, M. J. Tetrahedron Lett. 2005, 46, 6893-6896.
23. Kim, D. S. H. L.; Kim, J. Y. Bioorg. Med. Chem. Lett. 2004, 14, 1287-1289.
24. Luo, S.; Mi, X.; Zhang, L.; Liu, S.; Xu, H.; Cheng, J. P.
Tetrahedron Lett. 2007, 63, 1923-1930.
25. Nascimento, I. R.; Lopes, L. M. X.; Davin, L. B.; Lewis, N. G. Tetrahedron Lett. 2000, 56, 9198-9193.