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研究生:陳嘉珮
研究生(外文):Chai-pei Chen
論文名稱:利用γ-氧化鋁固態擔體催化合成2-芳香基苯並噻唑與3-苯並噻唑基香豆素
論文名稱(外文):γ-Alumina as a Support and Catalyst for Synthesis of 2-Arylbenzothiazoles and 3-Benzothiazoylcoumarins
指導教授:林孝道
指導教授(外文):Shaw-tao Lin
學位類別:碩士
校院名稱:靜宜大學
系所名稱:應用化學研究所
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:2010
畢業學年度:98
語文別:中文
論文頁數:115
中文關鍵詞:微波3-苯並噻唑香豆素無溶劑2-芳香基苯並噻唑固態擔體
外文關鍵詞:microwavesolvent-free 3-benzothiazoylcoumarins2-arylbenzothiazolessolid supporting material
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在無溶劑條件下,將2-胺基硫酚與苯甲醛以不同固態擔體催化合成2-芳香基苯並噻唑系列化合物。其中又以使用γ-Al2O3為固態擔體時反應性最佳。
當以生成速率與Hammettt常數(σ)作圖時,可得到一斜率為0.57相關係數為0.91的線性關係,此關係顯示出2-胺基硫酚與苯甲醛的反應速率受到苯甲醛醛基上碳原子接受親核性試劑的能力影響。
此外,過去需以強酸溶劑才可得到3-苯並噻唑基香豆素衍生物,在此則是利用γ-Al2O3並加入適量的五氧化二磷,於無溶劑的情況下製備3-苯並噻唑基香豆素衍生物。
在熱源的反應性比較上我們也以傳統加熱和聚焦式微波作比較,而由於聚焦式微波傳熱較傳統加熱快速,大幅縮短反應時間。
Among the used solid support in solvent-free condition for synthesis of 2-arylbenzothiazoles, the γ-alumina is the best one in terms of conversion rate.
The formation of benzothiazoles is a substituent dependant. The linear correlation between formation rates of benzothiazoles and Hammett constants(σ) is a small positive line(slop = 0.57, R2= 0.91) which reflects that a nucleophilicity of the carbon of aldehyde is main factor for this reaction.
We preparaed high intense fluoreseence 3-benzothiazoylcoumarins from 3-ethoxycarbonyl coumarin and 2-aminothiophenol in solvent free condition.
The preparation of benzothiazoles is also investingated by using either traditional heating or microwave heating. The later demonstrated higher efficiency for formation the titled compounds.
中文摘要.................................................Ⅰ
英文摘要.................................................Ⅱ
第一章 緒論..............................................1
1-1、前言...............................................1
1-2、固態擔體(Solid Support Material).......................4
1-2-1、固態擔體在合成上之應用.......................5
1-2-2、氧化鋁的介紹.................................6
1-3、苯並噻唑(Benzothiazole)..............................9
1-3-1、苯並噻唑的介紹...............................9
1-3-2、合成方法....................................10
1-3-3、命名........................................13
1-4、香豆素(Coumarin)...................................14
1-4-1、香豆素介紹..................................14
1-4-2、雜環香豆素命名..............................19
1-5、微波合成技術......................................20
1-5-1、微波加熱理論................................22
1-5-2、微波反應器種類..............................23
1-5-3、聚焦式微波在合成反應上之應用................24
1-5-4、實驗所採用微波裝置..........................25
1-6、Hammett 方程式....................................26
1-7、實驗設計程........................................28
1-7-1、2-芳香基苯並噻唑.............................28
1-7-2、3-苯並噻唑基香豆素...........................29
第二章 結果與討論.......................................30
2-1、2-芳香基苯並噻唑製備..............................30
2-2、3-乙氧羰基香豆素製備..............................49
2-2-1、3-乙氧羰基香豆素結構確認....................40
2-2-2、3-乙氧羰基6-取代基及8-取代基香豆素結構確認...41
2-3、3-苯並噻唑基香豆素製備............................ 43
2-3-1、3-苯並噻唑基香豆素系列化合物結構確認.........47
第三章 結論.............................................48
第四章 實驗步驟與數據...................................49
4-1、2-芳香基苯並噻唑製備..............................49
4-2、2-芳香基苯並噻唑之光譜數據........................50
4-3、3-乙氧羰基香豆素製備..............................58
4-4、3-乙氧羰基香豆素之光譜數據.......................59
4-5、3-苯並噻唑基香豆素製備...........................61
4-6、3-苯並噻唑基香豆素之光譜數據.....................62
第五章 實驗儀器與藥品...................................66
參考文獻.................................................71
附圖.....................................................82
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