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研究生:林懏濝
論文名稱:利用碘催化以及一鍋到底的方法合成具有生物活性的分子片段
論文名稱(外文):One-pot synthesis of bioactive molecular fragment using iodine as catalyst
指導教授:姚清發姚清發引用關係
學位類別:博士
校院名稱:國立臺灣師範大學
系所名稱:化學系
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2005
畢業學年度:94
語文別:英文
論文頁數:364
中文關鍵詞:催化一鍋合成
相關次數:
  • 被引用被引用:0
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第一部份 中文摘要
在室溫下,利用碘(iodine)催化indole和pyrrol對nitroolefins進行Michael加成進而得到indolyl nitroalkane 5 和 pyrrolyl nitroalkane 7。相較於已知的路易士酸或貴重金屬當催化劑來說,此方法具有反應時間短及高產率的優點。

第二部份 中文摘要
在無溶劑的條件之下,利用碘 (iodine) 及2,4,6-trichloro﹝1,3,5﹞triazine (TCT) 加速醛 (aldehyde) 或酮 (ketone)、苯胺(aniline) 和亞磷酸三乙酯 (triethylphosphite)合成-胺基磷酸鹽類(-amino phosphonate),此反應可在室溫或是60 oC條件下,以一鍋的方式進行反應得到高產率的產物。

第三部份 中文摘要
在室溫下,利用碘(iodine)催化醛、苯胺和acetylcyclohenxene以具有選擇性的特性,一鍋合成trans-endo-decahydroquinolin-4-one;此方法具有易操作、反應時間短、高產率、單一產物已及溫和的反應條件的優點。

第四部份 中文摘要
利用碘(iodine)催化醛和2-hydroxyacetophenone一鍋合成flavanone,此方法具有易操作、高產率、單一產物以及適用於各種官能基的優點。

第五部份 中文摘要
3-Amino chromans的衍生物在神經生物學及藥物學上,扮演極重要的腳色,因此發展有效率的合成方法為當務之急。我們利用salicylaldehyde 1 和nitromethane 經由 Knovenagel 反應路徑,接著走Michael 加成及aldol 的反應機構,在一鍋的條件下,合成出3-amino chromans的衍生物。
Part 1. I2-Catalyzed Michael Addition of Indole and Pyrrole to Nitroolefins 1

English Abstract 2

Chinese Abstract 3

Introduction 4

Result and Discussion 6

Conclusion 15

Experimental Section 16

General 16

Material 16

Procedure and NMR data 17

Reference 27

Spectrum Data and X-Ray Data 33




Part 2. Nonmetal Catalysts of Iodine and TCT Promote the One-pot Synthesis of Amino Phosphonates from Aldehydes or Ketones, Aniline, and Triethylphosphite Under Solvent
Free Conditions 87

English Abstract 88

Chinese Abstract 89

Introduction 90

Result and Discussion 93

Conclusion 101

Experimental Section 102

General 102

Material 102

Procedure and NMR data 103

Reference 118

Spectrum Data and X-Ray Data 124




Part 3. Stereoselective of Three-component Synthesis of trans-endo-decahydroquinolin-4-one Derivatives from Aldehydes, Aniline and Acetylcyclohexene 161

English Abstract 162

Chinese Abstract 163

Introduction 164

Result and Discussion 167

Conclusion 173

Experimental Section 174

General 174

Material 174

Procedure and NMR data 174

Reference 183

Spectrum Data and X-Ray Data 187





Part 4. One-Pot Synthesis of a Flavanone, Giving a Single Product in High Yield 291

English Abstract 292

Chinese Abstract 293

Introduction 294

Result and Discussion 296

Conclusion 303

Experimental Section 303

General 303

Material 304

Procedure and NMR data 304

Reference 309

Spectrum Data and X-Ray Data 315


Part 5. One-Pot Synthesis of 3-Nitrochroman 343

English Abstract 344

Chinese Abstract 345

Introduction 346

Result and Discussion 349

Conclusion 355

Experimental Section 355

General 355

Material 356

Procedure and NMR data 356

Reference 360

Spectrum Data and X-Ray Data 364
part 1 Reference

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part 2 Reference

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part 3 Reference

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5. (a) Kim, K. M.; Ryu, E. K. Tetrahedron Lett. 1996, 37, 1441. (b) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. J. Org. Chem. 2001, 66, 7527. (c) Firouzabadi, H.; Iranpoor, N.; Sobhani, S. Tetrahedron Lett. 2002, 43, 3653. (d) Yadav, J. S.; Reddy, B. V. S.; Reddy, M. S.; Prasad, A. R. Tetrahedron Lett. 2002, 43, 9703. (e) Bandgar, B. P.; Shaikh, K. A. Tetrahedron Lett. 2003, 44, 1959. (f) Saeeng, R.; Sirion, U.; Sahakitpichan, P.; Isobe, M. Tetrahedron Lett. 2003, 44, 6211. (g) Yadav, J. S.; Reddy, B. V. S.; Shubashree, S.; Sadashiv, K. Tetrahedron Lett. 2004, 45, 2951. (h) Phukan, P. J. Org. Chem. 2004, 69, 4005. (i) Phukan, P. Tetrahedron Lett. 2004, 45, 4785. (j) Sun, J.; Dong, Y; Wang, X.; Wang, S.; Hu, Y. J. Org. Chem. 2004, 69, 8932. (k) Bhosale, R. S.; Bhosale, S. V.; Bhosale, S. V.; Wang, T.; Zubaidha, P. K. Tetrahedron Lett. 2004, 45, 9111. (l) Ke, B.; Qin, Y.; He, Q.; Huang, Z.; Wang, F. Tetrahedron Lett. 2005, 46, 1751. (m) Banik, B. K.; Fernandez, M.; Alvarez, C. Tetrahedron Lett. 2005, 45, 2479. (n) Chu, C.-M.; Gao, S.; Sastry, M. N. V.; Yao, C.-F. Tetrahedron Lett, 2005, 46, 4971. (o) Ko, S.; Sastry, M. N. V.; Lin, C.; Yao, C.-F. Tetrahedron Lett, 2005, 46, 5771. (p) Shivaji, V. M.; Sastry, M. N. V.; Wang, C.-C.; Yao, C.-F. Tetrahedron Lett. 2005, 46, 6345. (q) Lin, C.; Hsu, J.; Sastry, M. N. V.; Fang, H.; Tu, Z.; Liu, J.-T.; Yao, C.-F. Tetrahedron 2005, 61, 11751. (r) Ko, S.; Lin, C.; Tu, Zhijay,; Wang, Y.-F.; Wang, C.-C.; Yao, C.-F. Tetrahedron Lett. 2006, 47, 487. (s) Gao, S.; Tzeng, T.; Sastry, M. N. V.; Chu, C.-M.; Liu, J.-T.; Lin, C.; Yao, C.-F. Tetrahedron Lett. 2006, 47, 1889.
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part 4 Reference

1. (a) Khattab, A. M.; Grace, M. H.; El-Khrisy, E. A. Pharmazie 2001, 56, 661; (b) Horie, T.; Tominaga, H.; Kawamura, Y.; Hada, T.; Ueda, N.; Amano, Y.; Yamamoto, S. J. Med.Chem. 1991, 34, 2169; (c) van Acker, F. A. A.; Hageman, J. A.; Haenen, G. R. M. M.; van der Vijgh, W. J. F.; Bast, A.; Menge, W. M. P. B. J. Med. Chem. 2000, 43, 3752; (d) Nussbaumer, P.; Lehr, P.; Billich, A. J. Med. Chem. 2002, 45, 4310; (e) Souza, J.; Molfetta, J. F. A.; Honorio, K. M.; Santos, R. H. A.; Silva, A. B. F. J. Chem. Inf. Comput. Sci. 2004, 44, 1153; (f) Zhou, Z.; Zhao, P.; Huang, W.; Yang, G. Adv. Synth. Catal. 2006, 348, 63.
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15. (a) Kim, K. M.; Ryu, E. K. Tetrahedron Lett. 1996, 37, 1441. (b) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. J. Org. Chem. 2001, 66, 7527. (c) Firouzabadi, H.; Iranpoor, N.; Sobhani, S. Tetrahedron Lett. 2002, 43, 3653. (d) Yadav, J. S.; Reddy, B. V. S.; Reddy, M. S.; Prasad, A. R. Tetrahedron Lett. 2002, 43, 9703. (e) Bandgar, B. P.; Shaikh, K. A. Tetrahedron Lett. 2003, 44, 1959. (f) Saeeng, R.; Sirion, U.; Sahakitpichan, P.; Isobe, M. Tetrahedron Lett. 2003, 44, 6211. (g) Yadav, J. S.; Reddy, B. V. S.; Shubashree, S.; Sadashiv, K. Tetrahedron Lett. 2004, 45, 2951. (h) Phukan, P. J. Org. Chem. 2004, 69, 4005. (i) Phukan, P. Tetrahedron Lett. 2004, 45, 4785. (j) Sun, J.; Dong, Y; Wang, X.; Wang, S.; Hu, Y. J. Org. Chem. 2004, 69, 8932. (k) Bhosale, R. S.; Bhosale, S. V.; Bhosale, S. V.; Wang, T.; Zubaidha, P. K. Tetrahedron Lett. 2004, 45, 9111. (l) Ke, B.; Qin, Y.; He, Q.; Huang, Z.; Wang, F. Tetrahedron Lett. 2005, 46, 1751. (m) Banik, B. K.; Fernandez, M.; Alvarez, C. Tetrahedron Lett. 2005, 45, 2479. (n) Chu, C.-M.; Gao, S.; Sastry, M. N. V.; Yao, C.-F. Tetrahedron Lett, 2005, 46, 4971. (o) Ko, S.; Sastry, M. N. V.; Lin, C.; Yao, C.-F. Tetrahedron Lett, 2005, 46, 5771. (p) Shivaji, V. M.; Sastry, M. N. V.; Wang, C.-C.; Yao, C.-F. Tetrahedron Lett. 2005, 46, 6345. (q) Lin, C.; Hsu, J.; Sastry, M. N. V.; Fang, H.; Tu, Z.; Liu, J.-T.; Yao, C.-F. Tetrahedron 2005, 61, 11751. (r) Ko, S.; Lin, C.; Tu, Zhijay,; Wang, Y.-F.; Wang, C.-C.; Yao, C.-F. Tetrahedron Lett. 2006, 47, 487. (s) Gao, S.; Tzeng, T.; Sastry, M. N. V.; Chu, C.-M.; Liu, J.-T.; Lin, C.; Yao, C.-F. Tetrahedron Lett. 2006, 47, 1889.




part 5 Reference

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1. 利用碘化銅及雙胺配基催化醯亞胺與芳香基鹵化物之碳-氮鍵偶合反應
2. (1)合成碳-配醣體的研究:以碘分子誘導和催化D-glucal與1,3-雙羰基化合物反應(2)以三甲基碘矽烷催化D-glucal製備2-去氧糖類分子
3. 利用碘催化以及一鍋式方法合成具有生物活性的十氫喹啉及黃烷酮衍生物
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8. 碘乙烷催化劑對銅化學氣相沉積特性之影響
9. 芳香碘化物和三甲基矽乙炔的鈀催化偶合反應
10. 鎳金屬錯合物催化7-異合雙環[2.2.1]庚二烯與末端炔及有機碘化物之耦合反應的探討
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6. 合成硫酸化N-乙醯乳醣胺及其衍生物以用於半乳醣凝集素結合專一性之研究
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10. 利用碘化銅及雙胺配基催化醯亞胺與芳香基鹵化物之碳-氮鍵偶合反應
11. 壹、不飽和羰基與硝基化物:促進有機硫化物在合成與催化之應用;貳、高效碘催化芳香烴環與苯乙烯系列物之加成反應;參、吡唑衍生物在類大麻素受體拮抗劑之合成和結構與活性關係
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14. 紫質在溶液中、生物與奈米環境下的光譜與緩解動力學研究
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