臺灣博碩士論文加值系統

雙黃酮類化合物常見於天然植物中，主要應用在抑制B型肝炎病毒、抗癌和增強免疫能力。本實驗利用Baker-Venkataraman重排反應合成6-甲氧基黃酮，再採用電化學雙聚合方法探討雙黃酮合成應用研究，瞭解黃酮類化合物之電化學反應及其影響的因素。6-甲氧基黃酮的電解還原反應，得到兩種產物分別為6,6’-二甲氧基-2,2’-外消旋雙黃烷酮和6,6’-二甲氧基-2,2’-內消旋雙黃烷酮，另有一還原產物6-甲氧基黃烷酮，並發現起產物產率明顯受到電極材料、電解質和反應溫度等各種因素影響。在反應條件0.1M甲醇硫酸、溫度0℃和0.01A定電流反應時，以鉛為因即可得到6,6’-二甲氧基-2,2’-外消旋雙黃烷酮和6,6’-二甲氧基-2,2’-內消旋雙黃烷酮較高產率。

Biflavonoids usually exist in natural plants. They were found to have some activities in hepatitis B virus, anti-cancer,anti-spasm, improving immunity. 6-Methoxyflavone were synthesized by Baker- Venkataraman Rearrangement. We tried to invesgate the factors which affect the electroorganic dimerization of 6-methoxyflavone was easily reduced by using electrochemical method to give two hydrodimers of 6,6’-dimethoxy-2,2’-biflavanone (racemate) and 6,6’-dimethoxy-2,2’- biflavanone (meso) and one reductive product of 6-methoxyfiavaanone. Their yields were dependent on the nature of electrodes, the kinds of supporting electrolytes and the reaction temperature. They were found to afford higher yields of 6,6’-dimethoxy-2,2’-biflavanone (racemate), 6,6’-dimethoxy-2,2’-biflavanone (meso) and 6-methoxyfiavaanone.(24.9﹪, 22.9﹪,and38.5﹪,respectively,) in the reaction condition of Pd(-)/C(+)-0.1MH2SO4/MeOH-20F/mol at 0℃

致謝 Ⅰ
中文摘要 Ⅱ
英文摘要 Ⅲ
目錄 Ⅳ
圖目錄 Ⅵ
第一章 序論
1-1. 黃酮類化合物 1
1-2. 黃酮類化合物的合成 16
1-3. 雙黃酮類化合物 20
1-4. 雙黃酮類化合物的合成 25
1-5. 有機電化學合成 34
第二章 研究動機與構想
2-1. 研究動機 40
2-2. 合成構想 41
第三章 實驗部分
3-1. 儀器與試藥 44
3-2. 實驗步驟 47
第四章 結果與討論
4-1. 黃酮類化合物的合成 58
4-2. 2,2’-雙黃烷酮類化合物的合成 62
第五章 結論 69
第六章 參考文獻 71
第七章 附錄一
7-1. 紫外線吸收光譜 75
7-2. 紅外線吸收光譜 84
7-3. 核磁共振光譜 93
7-4. 質譜圖 111


圖目錄
1. 紫外線吸收光譜
附圖1. 1,4-二乙醯氧基苯(84)之紫外線吸收光譜 75
附圖2. 2,5-二羥基苯乙酮(85)之紫外線吸收光譜 76
附圖3. 2-羥基-5-甲氧基苯乙酮 (86)之紫外線吸收光譜圖 77
附圖4. 2-芐醯氯基-5-甲氧基苯乙酮(87)之紫外線吸收光譜圖 78
附圖5. 2-羥基-5-甲氧基-二芐醯基甲烷(88)之紫外線吸收光譜圖 79
附圖6. 6-甲氧基黃酮(89)之紫外線吸收光譜圖 80
附圖7. 6,6’-雙甲氧基-2,2’-外消旋黃烷酮(90a)之紫外線吸收光譜圖 81
附圖8. 6,6’-雙甲氧基-2,2’-內消旋黃烷酮(90b)之紫外線吸收光譜圖 82
附圖9. 6-甲氧基黃烷酮(91)之紫外線吸收光譜圖 83

2. 紅外線吸收光譜
附圖10. 1,4-二乙醯氧基苯(84)之紅外線吸收光譜 84
附圖11. 2,5-二羥基苯乙酮(85)之紅外線吸收光譜 85
附圖12. 2-羥基-5-甲氧基苯乙酮 (86)之紅外線吸收光譜圖 86
附圖13. 2-芐醯氯基-5-甲氧基苯乙酮(87)之紅外線吸收光譜圖 87
附圖14. 2-羥基-5-甲氧基-二芐醯基甲烷(88)之紅外線吸收光譜圖 88
附圖15. 6-甲氧基黃酮(89)之紅外線吸收光譜圖 89
附圖16. 6,6’-雙甲氧基-2,2’-外消旋黃烷酮(90a)之紅外線吸收光譜圖 90
附圖17. 6,6’-雙甲氧基-2,2’-內消旋黃烷酮(90b)之紅外線吸收光譜圖 91
附圖18. 6-甲氧基黃烷酮(91)之紅外線吸收光譜圖 92

3. 核磁共振光譜
附圖19. 1,4-二乙醯氧基苯(84)之氫核磁共振光譜圖 93
附圖20. 1,4-二乙醯氧基苯(84)之碳十三核磁共振光譜圖 94
附圖21. 2,5-二羥基苯乙酮(85)之氫核磁共振光譜圖 95
附圖22. 2,5-二羥基苯乙酮(85)之碳十三核磁共振光譜圖 96
附圖23. 2-羥基-5-甲氧基苯乙酮 (86)之氫核磁共振光譜圖 97
附圖24. 2-羥基-5-甲氧基苯乙酮 (86)之碳十三核磁共振光譜圖 98
附圖25. 2-芐醯氯基-5-甲氧基苯乙酮(87)之氫核磁共振光譜圖 99
附圖26. 2-芐醯氯基-5-甲氧基苯乙酮(87)之碳十三核磁共振光譜圖 100
附圖27. 2-羥基-5-甲氧基-二芐醯基甲烷(88)之氫核磁共振光譜圖 101
附圖28. 2-羥基-5-甲氧基-二芐醯基甲烷(88)之碳十三核磁共振光譜圖 102
附圖29. 6-甲氧基黃酮(89)之氫核磁共振光譜圖 103
附圖30. 6-甲氧基黃酮(89)之碳十三核磁共振光譜圖 104
附圖31. 6,6’-雙甲氧基-2,2’-外消旋黃烷酮(90a)之紅氫核磁共振光譜圖 105
附圖32. 6,6’-雙甲氧基-2,2’-外消旋黃烷酮(90a)之碳十三核磁共振光譜圖 106
附圖33. 6,6’-雙甲氧基-2,2’-內消旋黃烷酮(90b)之氫核磁共振光譜圖 107
附圖34. 6,6’-雙甲氧基-2,2’-內消旋黃烷酮(90b)之碳十三核磁共振光譜圖 108
附圖35. 6-甲氧基黃烷酮(91)之氫核磁共振光譜圖 109
附圖36. 6-甲氧基黃烷酮(91)之碳十三核磁共振光譜圖 110

4. 質譜圖
附圖37. 1,4-二乙醯氧基苯(84)之質譜圖 111
附圖38. 2,5-二羥基苯乙酮(85)之質譜圖 112
附圖39. 2-羥基-5-甲氧基苯乙酮 (86)之質譜圖 113
附圖40. 2-芐醯氯基-5-甲氧基苯乙酮(87)之質譜圖 114
附圖41. 2-羥基-5-甲氧基-二芐醯基甲烷(88)之質譜圖 115
附圖42. 6-甲氧基黃酮(89)之質譜圖 116

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