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論文名稱 Title |
(一)鄰位-甲氧基二苯乙烯及其衍生物之熱解與光解研究
(二)N-(N-甲基-3-吲哚基)甲基苯甲醯胺之熱解研究 (一) Pyrolytic and Photolytic Studies of o-Methoxy stilbene and Its Derivatives (二) Pyrolytic study of N-(N-Methyl-3-indolyl)methyl benzamide |
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系所名稱 Department |
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畢業學年期 Year, semester |
語文別 Language |
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學位類別 Degree |
頁數 Number of pages |
160 |
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研究生 Author |
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指導教授 Advisor |
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召集委員 Convenor |
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口試委員 Advisory Committee |
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口試日期 Date of Exam |
2009-07-02 |
繳交日期 Date of Submission |
2009-07-27 |
關鍵字 Keywords |
光解、2-芳香基苯駢[b]呋喃、瞬間真空熱解法 2-arylbenzo[b]furan, flash vacuum pyrolysis, photolysis |
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統計 Statistics |
本論文已被瀏覽 5670 次,被下載 0 次 The thesis/dissertation has been browsed 5670 times, has been downloaded 0 times. |
中文摘要 |
(一)本部份以反式 (trans) 的鄰-甲氧基二苯乙烯及其衍生物47a-f進行熱解及光解研究,發現熱解部份除了得到預期產物2-芳香基苯駢[b]呋喃的產物52a,c-f之外,尚得到其異構物53a,c-d。其中化合物47b的熱解,由於呋喃環 (furan) 高溫下開環重排會形成主產物萘 (63) 的架構;另一部份光解結果發現,得到的產物均符合預期的結果。(二)本部份以N-(N-甲基-3-吲哚基)甲基苯甲醯胺 (45) 為起始物,在 瞬間真空熱解的反應條件下進行裂解反應,得到擴環產物3-甲基喹啉 (38)、4-甲基喹啉 (39) 和二次裂解的產物喹啉 (36)。 (二)本部份以N-(N-甲基-3-吲哚基)甲基苯甲醯胺 (45) 為起始物,在 瞬間真空熱解的反應條件下進行裂解反應,得到擴環產物3-甲基喹啉 (38)、4-甲基喹啉 (39) 和二次裂解的產物喹啉 (36)。 |
Abstract |
1.trans o-methoxystilbene and its derivatives 47a-f had been studied by means of pyrolysis and photolysis. Under pyrolytic conditions, compounds 47a-f gave not only the expected products 52a,c-f, but also their corresponding isomers 53a,c-f . Furthermore, compound 47b gave naphthalene (63) as the major product by opening the furan ring at higher temperature. Under photolytic conditions, compounds 47a-f gave the expected photocyclic products 2a-f and 109a-f.2.Pyrolytic chemistry of N-(N-Methyl-3-indolyl)methyl benzamide (45) hes been studied. Pyrolysis of 45 gave 3-methyl quinoline (38), 4-methyl quinoline (39) and secondary pyrolysis product quinoline (36). 2.Pyrolytic chemistry of N-(N-Methyl-3-indolyl)methyl benzamide (45) hes been studied. Pyrolysis of 45 gave 3-methyl quinoline (38), 4-methyl quinoline (39) and secondary pyrolysis product quinoline (36). |
目次 Table of Contents |
第一章 鄰位-甲氧基二苯乙烯及其衍生物之熱解與光解研究 壹、緒論 1 貳、結果與討論 23 參、結論 62 肆、實驗部份 64 伍、參考文獻 111 第二章 N-(N-甲基-3-吲哚基)甲基苯甲醯胺之熱解研究 壹、緒論 117 貳、結果與討論 130 參、結論 136 肆、實驗部份 138 伍、參考文獻 146 |
參考文獻 References |
(一)1. Hammond, G. S.; Saltiel, J. J. Am. Chem. Soc. 1962, 84, 4983-4984. 2. Mallory, F. B.; Wood, C. S.; Gordon, J. T.; Lindquist, L. C.; Savitz, M. L. J. Am. Chem. Soc. 1962, 84, 4361-4362. 3. Kupchan, S. M.; Wormser, H. C. Tetrahedron Lett. 1965, 6, 359-365. 4. Lewis, F. D. Acc. Chem. Res. 1979, 12, 152-158. 5. (a) Lewis, F. D.; Ho. T. I.; Simpson, J. T. J. Am. Chem. Soc. 1982, 104, 1924-1929. (b) Yasuda, M.; Isami, T. Kubo, J.; Mizutani, M.; Shima, K.; Yamashita, T. J. Org. Chem. 1992, 57, 1351-1354. 6. Somers, J. B. M.; Couture, A.; Lablache-Combier, A.; Laarhoven, W. H. J. Am. Chem. Soc. 1985, 107, 1387-1394. 7. Mallory, F. B.; Wood, C. S.; Gordon, J. T. J. Am. Chem. Soc. 1964, 86, 3094-3102. 8. Loader, C. E.; Timmons, C. J. J. Chem. Soc. (C) 1967, 1677-1681. 9. Curruthers, W.; Stewart, H. N. W. Tetrahedron Lett. 1965, 6, 301-302. 10. Ho, T. I.; Wang, S. Li.; Wu, J. Y. Angew. Chem. Int. Ed. 1999, 38, 2558-2560. 11. (a) Ho, T. I.; Ho, J. H.; Wu, J. Y. J. Am. Chem. Soc. 2000, 122, 8575-8576. (b) Ho, T. I.; Ho, J. H.; Liu, R. S. H. Org. Lett. 2001, 3, 409-411. 12. Ho, T. I.; Ho, J. H. Tetrahedron Lett. 2003, 44, 4669-4672. 13. Plater, M. J. Tetrahedron Lett. 1994, 35, 801-802. 14. 國立中山大學化學研究所研究生柳依克之碩士論文,中華民國九十七年六月。 15. Schopfer, U.; Schoeffter, P.; Serge, F. B.; Nozulak, J.; Feuerbach, D.; Floersheim, D.; Floersheim, P. J. Med. Chem. 2002, 45, 1399-1401. 16. Durst, T.; Chauret, D. C.; Bernard, C. B.; Arnason J. T. J. Nat. Prod. 1996, 59, 152-155. 17. Cañigueral, S.; Freixa, B.; Vila, R.; Adzet, T.; Ferro, E. A. Planta Med. 2001, 67, 873-875. 18. Naito, T.; Miyata, O.; Takeda, N. Org. Lett. 2004, 6, 1761-1763. 19. Tsai, I. L.; Hsieh, C. F.; Duh, C. Y. Phytochemistry 1998, 48, 1371-1375. 20. Lee, C. M.; Wong, H. N. C.; Cui, Y. X.; Yang, Z.; Hon, P. M.; Chui, K. Y.; Xu, Z. L.; Chang, H. M.; Poon, C. D.; Fung, B. M. Tetrahedron Lett. 1991, 32, 2061-2064. 21. Greger, H.; Hofer, O.; Pacher, T.; Engelmeier, D.; Vajrodaya, S. J. Nat. Prod. 2002, 65, 820-827. 22. Chen, Y.; Wei, X.; Xie, H.; Deng, H. J. Nat. Prod. 2008, 71, 929-932. 23. Duan, X. F.; Zeng, J.; Zhang, Z. B.; Zi, G. F. J. Org. Chem. 2007, 72, 10283-10286. 24. Wang, Z.; Pan, C.; Yu, J.; Zhou, Y.; Zhou, M. M. Synlett. 2006, 1657-1662. 25. Imafuku, K.; Fujita, R. Chem. Express 1991, 6, 323-326. 26. Jørgensen, M.; Krebs, F. C.; Bechgaard, K. J. Org. Chem. 2000, 65, 8783-8785. 27. Larock, R.; Yue, D.; Yao, T. J. Org. Chem. 2005, 70, 10292-10296. 28. Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett. 1999, 1432-1434. 29. Venkataraman, D.; Bates, C. G.; Saejueng, P.; Murphy, J. M. Org. Lett. 2002, 4, 4727-4729. 30. Domínguez, E.; Carril, M.; SanMartin, R.; Tellitu, I. Org. Lett. 2006, 8, 1467-1470. 31. Chen, C. Y. ; Dormer, P. G. J. Org. Chem. 2005, 70, 6964-6967. 32. Domínguez, E.; SanMartin, R.; Churruca, F.; Tellitu, I. Eur. J. Org. Chem. 2005, 2481-2490. 33. Banerji, A.; Nayak, S. K. J. Chem. Soc., Chem. Commun. 1990, 150-151. 34. Fürstner, A.; Jumbam, D. N. Tetrahedron 1992, 48, 5991-6010. 35. Chattopadhyay, S.; Rele, S.; Talukdar, S.; Banerji, A. J. Org. Chem. 2001, 66, 2990-2994. 36. Jirí, S.; Katerina, C.; Miloslav, N.; Pavel, P. Collect. Czech. Chem. Commun. 2000, 65, 1939-1949. 37. Katritzky, A. R.; Ji, Y.; Fang, Y.; Prakash, I. J. Org. Chem. 2001, 66, 5613-5615. 38. Cadogan, J. I.; G.; McNab, H.; Black, M.; MacPherson, A. D.; Roddam, V. P.; Simith, C.; Swenson, H. R. J. Chem. Soc., Perkin Trans. 1 1997, 17, 2483-2494. 39. Harrison, A. G.; Honnen, L. R.; Dauben, H. J.; Lossing, F. P. J. Am. Chem. Soc. 1960, 82, 5593-5598. 40. 國立中山大學化學研究所研究生朱立澤之博士論文,中華民國九十四年六月。 41. Alder, R. W.; East, S. P.; Harvey, J. N.; Oakley, M. T. J. Am. Chem. Soc. 2003, 125, 5375-5387. 42. 國立中山大學化學研究所研究生許躍騰之博士論文,中華民國九十四年六月。 43. Luo, Y. R. “ Handbook of Bond Dissociation Energies in Organic Compounds. ” CRC Press, New York, 2003 44. Jacobson, I. A.; Jensen, H. B. J. Phys. Chem. 1962, 66, 1245-1247. 45. Patterson, J. M.; de Haan, J. W.; Boyd, M. R.; Ferry, J. D. J. Am. Chem. Soc. 1972, 94, 2487-2494. 46. (a) Patterson, J. M.; Brasch, J.; Drenchko, P. J. Org. Chem. 1961, 27, 1652-1659. (b) Patterson, J. M.; Soedigdo, S. J. Org. Chem. 1967, 32, 2969-2972. 47. Semmelhack, M. F.; Weller, H. N.; Foos, J. S. J. Am. Chem. Soc. 1977, 99, 292-294. 48. Mallory, F. B.; Rudolph, M. J.; Oh, S. M. J. Org. Chem. 1989, 54, 4619-4626. 49. Wang, C.; Pan, Y.; Wu, A. Tetrahedron 2007, 63, 429-434. 50. Amin, S.; Hecht, S.S.; Hoffmann, D. J. Org. Chem. 1981, 46, 2349- 2398. 51. Song, C.; Ma, Y.; Chai, Q.; Ma, C.; Jiang, W.; Andrus, M. B. Tetrahedron 2005, 61, 7438-7446. 52. Ghosh, S.; Banerjee, I.; Baul, S. Tetrahedron 1999, 55, 11537-11546. 53. (a) Kashulin, I. A.; Nifant'ev, I. E. J. Org. Chem. 2004, 69, 5476-5479. (b) Katrizky, A. R. ; Ji, Y.; Fang, Y.; Prakash, I. J. Org. Chem. 2001, 66, 5613-5615. (c) Liu, G.; Lu, X. Tetrahedron 2008, 64, 7324-7330. 54. Ibrahim, Y. A.; Al-Awadi, N. A.; Kaul, K. Tetrahedron 2001, 57, 7377-7381. 55. Ho, J. H.; Lin, J. H.; Ho, T. I. J. Chin. Chem. Soc. 2005, 52, 805-810. 56. Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017-8028. 57. Fiandanese, Vito.; Bottalico, D.; Marchese, G.; Punzi, A. Tetrahedron 2008, 64, 53-60. 58. (a) Tsuchimoto, T.; Matsubayashi, H.; Kaneko, M.; SHirakawa, E.; Kawakami, Y. Angew. Chem. Int. Ed. 2005, 44, 1336-1340. (b) Hudkins, R. L.; Diebold, J. L.; Marsh, F. D. J. Org. Chem. 1995, 60, 6218-6220. 59. Grellmann, K. H.; Schmitt, U. J. Am. Chem. Soc. 1982, 104, 6267- 6272. 60. Pedersen, J. M.; Bowman, W. R.; Elsegood, M. R. J.; Fletcher, A. J.; Lovell, P. J. J. Org. Chem. 2005, 70, 10615-10618. 61. Furstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264-6267. 62. Black, M.; Cadogan, J. I. G.; McNab, H.; MacPherson, A. D.; Roddam, V. P.; Smith, C.; Swerson, H. R. J. Chem. Soc., Perkin Trans 1, 1997, 2483-2493. 63. Baumgartner, M. T.; Pierini, A. B.; Rossi, R. A. J. Org. Chem. 1993, 58, 2593-2598. (二)1. Kirmse, W. “Carbene Chemistry.” Academic Press, New York, 1971 2. McManus, S. P. “Organic Reactive Intermediates.” Academic Press, New York, 1973 3. Rappoport, Z. “ The Chemistry of the Cyclopropyl Group.” PartII. John Wiley and Sons, New York, 1987 4. Lehr. R. E.; Marchand, A. P., eds. “ Pericyclic Reactions.” Vol. 1. Academic Press, New York, 1977 5. Greenberg, A.; Liebman, J. H. “Strained Organic Molecules.” Academic Press, New York, 1978 6. Brown, R. F. C. “ Pyrolytic Methods in Organic Chemeistry.” Academic Press, New York, 1980 7. Chapman, O. L.; Tsou, U. P. E. J. Am. Chem. Soc. 1984, 106, 7974-7976. 8. Chapman, O. L.; Tsou, U. P. E.; Johnson, J. W. J. Am. Chem. Soc. 1987, 109, 553-559. 9. Hiue, J. S. “ Divalent Carbon.” Ronald Press, New York, 1964 10. Christensen, L. W.; Waali, E. E.; Jones, W. M. J. Am. Chem. Soc. 1972, 94, 2118-2119. 11. Moritani, I.; Murahashi, S.; Ashitaka, H.; Kimura, K.; Tsubomura, H. J. Am. Chem. Soc. 1968, 90, 5918-5919. 12. Hine, J.; Dowell, A. M. J. Am. Chem. Soc. 1954, 76, 2688-2692. 13. Skell, P. S.; Starer, I. J. Am. Chem. Soc. 1959, 81, 4117-4118. 14. Capon, B.; Perkins, M. J.; Ress, C. W. “Organic Reaction Mechanisms. 1965.” Interscience Publishers, New York, 1966 15. Capon, B.; Perkins, M. J.; Ress, C. W. “Organic Reaction Mechanisms. 1966.” Interscience Publishers, New York, 1967 16. Capon, B.;Perkins, M. J.; Ress, C. W. “Organic Reaction Mechanisms. 1967.” Interscience Publishers, New York, 1968 17. Mayor, C.; Wentrup, C. J. Am. Chem. Soc. 1975, 97, 7467-7480. 18. Schore, N. E. Chem. Rev. 1988, 88, 1081-1119. 19. Jones, W. M. Acc. Chem. Res. 1977, 10, 353-359. 20. Stouw, G. V.; Kraska, A. R.; Shechter, H. J. Am. Chem. Soc. 1972, 94, 1655-1661. 21. Sundberg, R. J.; Das, B. P.; Smith, R. H. J. Am. Chem. Soc. 1969, 91, 658-668. 22. Joines, R. C.; Turner, A. B.; Jones, W. M. J. Am. Chem. Soc. 1969, 91, 7754-7755. 23. Crow, W. D.; Lea, A. R.; Paddon-Row, M. N. Tetrahedron Lett. 1972, 22, 2235-2238. 24. Wentrup, C; Muller, P. Tetrahedron Lett. 1973, 31, 2915-2918. 25. Trahanovsky, W. S.; Park, M. G. J. Am. Chem. Soc. 1973, 95, 5412. 26. Trahanovsky, W. S.; Cassady, T. J.; Woods, T. L. J. Am. Chem. Soc. 1981, 103, 6691-6695. 27. Trahanovsky, W. S.; Amah, A. N.; Cassady, T. J. J. Am. Chem. Soc. 1984, 106, 2696-2698. 28. 國立中山大學化學研究所研究生曾本文之博士論文,中華民國八十三年六月。 29. 國立中山大學化學研究所研究生陳秉樞之博士論文,中華民國八十六年六月。 30. 國立中山大學化學研究所研究生龔振裕之碩士論文,中華民國八十三年六月。 31. Leete, E.; Marion, L. Can. J. Chem. 1953, 31, 775-784. 32. Gevorkyan, K. A.; Papayan, G. L.; Chshmarityan, S. G.; Paronikyan, R. G.; Akopyan, N. E. Pharmaceutical Chemistry Journal 1987, 765-769. 33. Nakao, Y.; Kanyiva, K. S.; Oda, S.; Hiyama, T. J. Am. Chem. Soc. 2006, 128, 8146-8147. 34. Ibrahim, Y. A.; Al-Awadi, N. A.; Kual, K. Tetrahedron 2003, 59, 5425-5430. 35. Huiban, M.; Huet, A.; Barre, L.; Sobrio, F.; Fouquet, E.; Perrio, C. Chem. Commun. 2006, 97-99 36. Ranu, B. C.; Hajra, A.; Dey, S. S.; Jana, U. Tetrahedron 2003, 59, 813-819. |
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