Basic Search / Detailed Display
| Author: |
吳詩慧 |
|---|---|
| Thesis Title: |
酸催化異喹啉、吡咯化合物的合成 |
| Advisor: | 葉名倉 |
| Degree: |
碩士 Master |
| Department: |
化學系 Department of Chemistry |
| Thesis Publication Year: | 2012 |
| Academic Year: | 100 |
| Language: | 中文 |
| Number of pages: | 106 |
| Keywords (in Chinese): | 含氮炔基之鏈環氧基環己酮 、雙三氟甲基磺醯亞胺 、三甲基矽基三氟甲基磺酸酯 、炔-酮置換反應 |
| Keywords (in English): | C-2 arylpropargylsulfonamide-tethered 2,3- epoxy-cyclohexan-1-ones, HNTf2, TMSOTf, alkyne-ketone metathesis |
| Thesis Type: | Academic thesis/ dissertation |
| Reference times: | Clicks: 356 Downloads: 1 |
| Share: |
| School Collection Retrieve National Library Collection Retrieve Error Report |
含氮炔基支鏈之環氧基環己酮使用催化量的雙三氟甲基磺醯亞胺(HNTf2)進行炔-酮置換反應，得到異喹啉化合物。
3,5,5-三甲基含氮炔基支鏈之環氧基環己酮使用催化量三甲基矽基三氟甲基磺酸酯(TMSOTf)進行串列－semipinacol重排反應/炔-酮置換反應，得到吡咯化合物。
以含有氘的含氮炔基支鏈的環氧基環己醇化合物在路易士酸的催化下進行semi-pinacol重排反應及炔－酮置換反應，得到螺旋化合物。經由13C NMR光譜圖，證明含氘的碳會根據2nI+1 Rule 分裂。
Reaction of the C-2 arylpropargylsulfonamide-tethered 2,3- epoxy-cyclohexan-1-ones with a catalytic amount of HNTf2 via alkyne-ketone metathesis provided isoquinolines.
Treatment of the substrates bearing a geminal dimethyl group at C-5 and a methyl group at C-3 of the ring with a catalytic amount of TMSOTf proceeded via semipinacol rearrangement/alkyne-ketone metathesis to afford pyrroles.
Synthesis of 9-benzoyl-7-tosyl-7-azaspiro[4.5]dec-9-en-10-d-1-one via TfOH-catalyzed tandem semi-pinacol rearrangement/alkyne-aldehyde metathesis. According to 2nI+1 Rule, the carbon which contains deuterium will be split into 3 peaks (a triplet).
1. Trost, B. M.; Tang, W. J. Am. Chem. Soc. 2002, 124, 14542-14543.
2. Trost, B. M.; Tang, W.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 14785-14803.
3. Hesses,M. Alkaloid Nature’s Curse or Blessing? Wiley-VCH: New York, p274.
4. Lohray, B. B.; Lohray V. Pure Appl. Chem. 2005, 77, 179-184.
5. Rossi, R.; Bellina, F. Tetrahedron 2006, 62, 7213-7156.
6. Büchi ,G.; Kofron, James T.; Koller, E.; Rosenthal, David J. Am. Chem. Soc. 1956, 78, 876-877.
7. Middleton, W. J. J. Org. Chem. 1965, 30, 1307.
8. Harding, Charles E.; Stanford, G. Richard Jr. J. Org. Chem. 1989, 54, 3054-3056.
9. Rhee, Jong Uk; Krische, Micheal J. Org. Lett. 2005, 7, 2493-2495.
10. Jin, T.; Yamamoto, Y. Org. Lett. 2007, 9, 5259-5262.
11. Jin, T.; Yang, F.; Liu,C.; Yamamoto, Y. Chem. Commun. 2009, 3533-3535.
12. Jin, T.; Himuro, M.; Yamamoto, Y. Angew. Chem. Int. Ed. 2009, 48, 5893-5896.
13. Liu,L.; Zhang, J. Angew. Chem. Int. Ed. 2009, 48, 6093-6096.
14. Kurtz, K. C. M.; Hsung, R. P.; Zhang, Y. Org. Lett. 2006, 8, 231-234.
15. Yeh, M. C. P.; Pai, H. F.; Hsiow, C. Y.; Wang, Y. R. Organometallics 2010, 29, 160–166.
16. Yeh, M. C. P.; Lin, M. N.; Chang, W. J.; Liou, J. L.; Shih, Y. F. J. Org. Chem. 2010, 75, 6031–6034.
17. Lin, M. N.; Wu, S. H.; Yeh, M. C. P. Adv. Synth. Catal. 2011, 353, 3290-3294.
18. Guerra, K. P.; Afonso, C. A. M. Tetrahedron 2011, 67, 2562- 2569.
19. Hara, R.; Furukawa, T.; Kashima, H.; Kusama, H.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1999, 121, 3072- 3082.
20. Godleski, S. A.; Valpey, R. S. J. Org. Chem. 1982, 47, 383-384.
21. Smith ΙΙΙ, A. B.; Branca, S. J.; Pilla, N. N.; Guaciaro, M. A. J. Org. Chem. 1982, 47, 1855-1869.
22. Nicolaou, K.C.; Ding, H.; Richard, J.-A.; Chen, D. Y.-K. J. Am. Chem. Soc. 2010, 132, 3815-3818.
