研究生: |
陳筱鳳 |
---|---|
論文名稱: |
金(I)催化1-芳香基-2-(3-芳香基丙炔基)環己-2-烯-1-醇的分子內環化反應:四氫苯并[b]呋喃衍生物的合成 Gold(I)-Catalyzed Intramolecular Cyclization of 1-Aryl-2-(3-arylpropargyl)cyclohex-2-en-1-ols: Synthesis of Tetrahydrobenzo[b]furan Derivatives |
指導教授: |
葉名倉
Yeh, Ming-Chang |
學位類別: |
碩士 Master |
系所名稱: |
化學系 Department of Chemistry |
論文出版年: | 2014 |
畢業學年度: | 102 |
語文別: | 中文 |
論文頁數: | 136 |
中文關鍵詞: | 苯并[b]呋喃 、金催化 、雜環 、三級醇 |
英文關鍵詞: | benzo[b]furan, gold catalyzed, heterocycle, tertiary alcohol |
論文種類: | 學術論文 |
相關次數: | 點閱:478 下載:2 |
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 |
本文探討以氯化三苯基膦金 ( Ph3PAuCl ) 和三氟甲磺酸銀 ( AgOTf ) 共催化2號位帶炔基支鏈的六員環三級烯醇化合物進行分子內環化反應。
1-芳香基-2-(3-芳香基丙炔基)環己-2-烯-1-醇與催化量的氯化三苯基膦金和三氟甲磺酸銀,在氮氣、室溫的條件下,行分子內環化反應,數分鐘內即可得四氫苯并[b]呋喃衍生物。
此反應亦可應用在三級醇上帶長鏈烷基及長鏈炔基質,得到一系列在2號位或4號位具不同烴取代的四氫苯并[b]呋喃衍生物。
The thesis discusses chloro(triphenylphosphine)gold(I) (Ph3PAuCl) and silver trifluoromethanesulfonate (AgOTf) cocatalyzed intramolecular cycloisomerization of 1-arylcyclohex-2-en-1-ols bearing an alkynylalkyl tether at the C-2 position of the ring.
Treatment of 1-aryl-2-(3-arylpropargyl)cyclohex-2-en-1-ols with a catalytic amount of Ph3PAuCl/AgOTf at room temperature under nitrogen in minutes provided tetrahydrobenzo[b]furan derivatives in good yields.
This reaction can be expanded to an alkyl substitution at the tertiary carbinol carbon and the terminal alkyne, leading to 2 or 4-alkylsubstituted tetrahydrobenzo[b]furan derivatives.
(1) Cai, X.-H.; Guo, H.; ISRN Organic Chemistry 2011, Article ID 239817
(2) Neumann, J.; Boerries, M.; Köhler, R,; Giaisi, M.; Krammer, P. H.; Busch,
H.; Weber, M.-L. Int. J. Cancer 2014, 134, 1991
(3) Gerard, B.; Jones, G., II; Porco, J. A.; Jr. J. Am. Chem. Soc. 2004, 126, 13620
(4) Chen, L.-J.; Lebetkin, E. H.; Burka, L. T. DMD 2003, 31, 1208
(5) Tsuboi, S.; Shimozuma, K.; Takeda, A. J. Org. Chem. 1980, 45, 1517
(6) Hayakawa, I.; Shioya, R.; Agatsuma, T.; Sugano, Y. Chem. Pharm. Bull.
2005, 53, 638
(7) Aranda, R.; Villalba, K.; Raviña, E.; Masaguer, C. F.; Brea, J.; Areias, F.; Domínguez, E.; Salent, J.; López, L.; Sanz, F.; Pastor, M.; Loza, M. I. J. Med. Chem. 2008, 51, 6085
(8) Isaka, M.; Sappan, M.; Rachtawee, P.; Boonpratuang, T. Phytochemistry
Letters 2011, 4, 106
(9) Pu, W.-C.; Mu, G.-M.; Zhang, G.-L.; Wang C. RSC Adv. 2014, 4, 903.
(10) Srikrishna, A.; Vijaykumar, D. J. Chem. Soc., Perkin Trans. 1 1999, 1265
(11) Lee, Y.-R.; Yoon, S.-H. Bull. Korean Chem. Soc. 2006, 27, 312
(12) Day, J. J.; McFadden, R. M.; Virgil, S. C.; Kolding, H.; Alleva, J. L.; Stoltz, B. M. Angew. Chem. Int. Ed. 2011, 50, 6814
(13) Fürstner, A.; Davies, P. W. Angew. Chem. Int. Ed. 2007, 46, 3410
(14) Hashmi, A. S. K.; Hutchings, G. J. Angew. Chem. Int. Ed. 2006, 45, 7896
(15) Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271
(16) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem Rev. 2008, 108, 3351
(17) Duan, H.; Sengupta, S.; Petersen, J. L.; Akhmedov, N. G.; Shi, X. J. Am. Chem. Soc. 2009, 131, 121001
(18) Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem. Int. Ed. 1998, 37, 1415
(19) Yoshida, M.; Ohno, S.; Shishido, K. Chem. Eur. J. 2012, 18, 1604
(20) Gabriele, B.; Veltri, L.; Plastina, P.; Mancuso, R.; Vetere, M. V.; Maltese, V. J. Org. Chem. 2013, 78, 4919
(21) Yao, T.; Zhang, X.; Larock, R. C. J. Org. Chem. 2005, 70, 7679
(22) Rauniyar, V.; Wang, Z. J.; Burks, H. E.; Toste, F. D. J. Am. Chem. Soc. 2011, 133, 8486
(23) Pei, T.; Chen, C.-Y.; DiMichele, L.; Davies, L. W. Org. Lett. 2010, 12, 4972
(24) Tsai, T.-W.; Wang, E.-C.; Li, S.-R.; Chen, Y.-H.; Lin, Y.-L.; Wang, Y.-F.; Huang, K.-S. J. Chin. Chem. Soc. 2004, 51, 1307
(25) Fürstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024
(26) Sakai, N.; Uchida, N.; Konakahara, T. Tetrahedron Lett. 2008, 49, 3437
(27). Sharma, U.; Naveen, T.; Maji, A.; Manna, S.; Maiti, D. Angew. Chem. Int. Ed. 2013, 52, 12669
(28) Wang, Jia-Rui, Manabe, K. J. Org. Chem. 2010, 75, 5340
(29) Wang, S.; Li, P.; Yu, L.; Wang, L. Org. Lett. 2011, 13, 5968
(30) Dwight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B. Org. Lett.
2007, 9, 3137
(31) Gay, R. M.; Manarin F.; Schneider C. C.; Barancelli, D. A.; Costa, M. D.; Zeni, G. J. Org. Chem. 2010, 75, 5701
(32) Zhou, L.; Zhang, M.; Li, W., Zhang, J. Angew. Chem. Int. Ed. 2014, 53, 6542
(33) Hashmi, A. S. K.; Yang, W.; Rominger, F. Angew. Chem. Int. Ed. 2011, 50, 5762
(34) Grisé, C. M.; Barriault, L. Org. Lett. 2006, 8, 5905
(35) Reich, N. W.; Yang, C.-G.; Shi, Z.; He, C. Synlett, 2006, 8, 1278
(36) Nguyen, R.-V.; Yao, X.; Li, C.-C. Org. Lett. 2006, 8, 2397
(37) Yeh, M.-C. P.; Lin, M.-N.; Chang, W.-J.; Liou, J.-L.; Shih, Y.-F. J. Org. Chem. 2010, 75, 6031
(38) Yeh, M.-C. P.; Pai, H.-F.; Hsiow, C.-Y.; Wang, Y.-R. Organometallics, 2010, 29, 160
(39) Yeh, M.-C. P.; Fang, C.-W.; Lin, H.-H. Org. Lett. 2012, 14, 1830
(40) Batey, R. A.; Harling, J. D.; Motherwell, W. B. Tetrahedron Lett. 1992, 48, 8031
(41)王妍蓉論文, 國立臺灣師範大學化學所, 2007年
(42) Rieke, R. D.; Kim, S. H.; Wu, X. J. Org. Chem. 1997, 62, 6921
(43) Du, Y.; Zheng. J.-F.; Wang, Z.-G.; Jiang, L.-J.; Ruan, Y.-P.; Huang, P.-Q. J. Org. Chem. 2010, 75, 4619
(44) Wang, T.; Shi, S.; Vilhelmsen, M. H.; Zhang, T; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Chem. Eur. J. 2013, 19, 12512
(45) Blanc, A.; Tenbrink, K.; Weibel. J.-M.; Pale, P. J. Org. Chem. 2009, 74, 5342
(46) Gabriele, B.; Salerno G.; Lauria E. J. Org. Chem. 1999, 64, 7687
(47) Ghebreghiorgis, T.;Biannic, B.; Hirk, B.H.; Ess, D. H.; Aponick, A. J. Am. Chem. Soc. 2012, 134, 16307
(48) Aponick, A.; Biannic, B. Org. Lett. 2011, 13, 1330
(49) Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.