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研究生:曾之緯
研究生(外文):Tze-Wei Tseng
論文名稱:各類芳香環并香豆素之合成法
論文名稱(外文):Various and versatile methodologies for the preparation of aryl- and heteroaryl- fused coumarins, and their application to the synthesis of natural compounds: Angelicin, Seselin, Xanthxyletin and Psoralen
指導教授:洪永叁
指導教授(外文):Yung-Son Hon
口試委員:洪伯誠許岱欣周德璋周必泰周大新廖俊臣洪永叁
口試委員(外文):Bor-Cherng HongDay-Shin HsuTeh-Chang ChouPi-Tai ChouTashin. J ChowChun-Chen LiaoYung-Son Hon
口試日期:2011-01-15
學位類別:博士
校院名稱:國立中正大學
系所名稱:化學研究所
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:2011
畢業學年度:99
語文別:中文
論文頁數:748
中文關鍵詞:苯并香豆素
外文關鍵詞:benzocoumarin
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以開發各類5,6-芳香環并香豆素與7,8-芳香環并香豆素的合成方法,並將其應用於天然物Angelicin, Seselin, Xanthxyletin and Psoralen的製備。
Various synthetic methods of benzocoumarins are described in this study.
In chapter 2, we have developed a new and useful method of preparing 5,6-benzocoumarins (2–2g) with different substituents on a variety of positions. Their molecular skeletons were formed from the oxidation of 2H-pyrans by DDQ reagent. These 2H-pyrans were prepared by tandem reaction of cis-hydrogenation of enynals and electrocyclization. Various α-tetralones were used as starting materials. Heteroarene-fused coumarins (2h–2k) were also prepared respectively.
In chapter 3, a modified synthetic route – α-tetralone keto ester was catalyzed by DBU– for Michael addation is described. The results
not only represent sizable yield of 7,8-benzocoumarins (3–3g, 22b, 22c, 26) under convenient conditions, but also provide an efficient route for the synthesis of some natural products, such as Angelicin (28), Seselin (33), and Pyrone (39, 39d).
In chapter 4, a new benzocoumarin building block method from β-tetralone has been discovered, under the condition of propiolic acid and HOTf, to give Claisen rearrangement products. The 5,6-benzocoumarin carbon skeleton from substituted β-tetralone was built up in 2 steps.
In final chapter, previous reaction condition was carried out naphthols and meta-substituted phenols. Aromatic coumarins (63–79) and some natural products (83, 87) were prepared respectively.
目錄
摘要 ------------------------------------------------------------------- I
目錄 ------------------------------------------------------------------------- V
圖表目錄 ------------------------------------------------------------- IX
縮寫對照表 ------------------------------------------------------------ X V I I
第一章 緒論 -------------------------------------------------------------- P. 1
1.1 背景介紹 -------------------------------------------------------- P. 1
1.2 研究緣起 -------------------------------------------------------- P. 2
1.3 文獻報導 ------------------------------------------------ P. 5
1.3.1 傳統方法合成香豆素 ----------------------------------------- P. 5
1.3.2 利用金屬催化合成香豆素 ------------------------------ P. 20
1.3.3 香豆素類化合物的研究與發展 ---------------------------- P. 36
1.3.4 以香豆素為螢光材料的發展與應用 ----------------------- P. 50
第二章 從1-四氫酮開始—獲得5,6-苯并香豆素的研究與方法 ------ P. 56
2.1 研究背景 ------------------------------------------------------------- P. 56
2.2策略I之逆合成分析:【由1-tetralone合成5,6-benzocoumarin】 --- P. 59
2.3 結果與討論 ------------------------------------------------ P.65
2.3.1【5,6-苯并香豆素的合成】-------------------------------------- P.65
2.3.2【5,6-雜環并香豆素的合成】------------------------------------ P.68
2.3.3【5,6-多環并香豆素的合成】----------------------------------- P. 71
2.3.4【進行其他實驗的研究】----------------------------------- P. 78
2.4策略II之逆合成分析:【由2-tetralone合成7,8-benzocoumarin】---- P.80
2.5 結果與討論 ----------------------------------------------- P.82
2.5.1【7,8-苯并香豆素的合成研究】------------------- P.82
2.6 結論 --------------------------------------------------------------- P. 84
第三章 從1-四氫酮開始—獲得7,8-苯并香豆素的研究與方法 ----- P. 86
3.1 研究背景 -------------------------------------- P. 86
3.2策略III之逆合成分析:
【由1-tetralone合成7,8-benzocoumarin (一)】------------------ P. 87
3.3 結果與討論【7,8-苯并香豆素的合成 (一)】 -------------------- P. 88
3.4策略III-2之逆合成分析:
【由1-tetralone合成7,8-benzocoumarin (二)】 ----------------- P. 95
3.5 結果與討論【7,8-苯并香豆素的合成 (二)】------------------ P. 96
3.6策略III-3之逆合成分析:
【由1-tetralone合成7,8-benzocoumarin (三)】------------------ P. 99
3.7 結果與討論【7,8-苯并香豆素的合成 (三)】------------------- P. 100
3.7.1【合成7,8-苯并香豆素的例子】 ---------------------- P. 107
3.7.2【合成7,8-雜環并香豆素的例子】----------------------- P. 108
3.7.3【應用至合成吡喃酮(Pyrone)的例子】---------------------- P. 114
3.7.4【進行其他實驗的研究】------------------------------- P. 119
3.8 結論 ------------------------------------------------------------ P. 120
第四章 從β-四氫酮開始—獲得5,6-苯并香豆素的研究與方法 --- P. 121
4.1 研究背景 ------------------------------------------------------------ P. 121
4.2策略IV之逆合成分析:
【由β-tetralone合成5,6-benzocoumarin (一)】--------- P. 122
4.3 結果與討論【5,6-苯并香豆素的合成 (一)】------------------- P. 123
4.4策略IV-2之逆合成分析:
【由β-tetralone合成5,6-benzocoumarin (二)】----------- P. 126
4.5 結果與討論【5,6-苯并香豆素的合成 (二)】---------------- P. 127
4.6策略IV-3之逆合成分析:
【由β-tetralone合成5,6-benzocoumarin (三)】------------------ P. 133
4.7 結果與討論【5,6-苯并香豆素的合成 (三)】--------------- P. 134
4.8策略IV-4之逆合成分析:
【由2-tetralone合成5,6-benzocoumarin (四)】------------------------ P. 135
4.9 結果與討論【5,6-苯并香豆素的合成 (四)】--------------- P. 136
4.10 結論 ------------------------------------------------------------ P. 139
第五章 從萘酚開始—一鍋化獲得多苯并香豆素的研究與方法 --- P.140
5.1 研究背景 -------------------------------------- P. 140
5.2 結果與討論【多芳香環并香豆素的合成】 ------------- P. 142
5.3 結果與討論【雜環并香豆素的合成】-------------- P. 159
5.4 結論 -------------------------------------------------------------P. 166
實驗 ---------------------------------------------- P. 167
(Uv-Vis)吸收與螢光放射量測 -------------------- P. 213
光譜數據 -------------------------------- P. 230
參考文獻 ----------------------------------------- P. 363
NMR圖譜 -------------------------------- P. 374
參考文獻
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