臺灣博碩士論文加值系統

本論文旨以綠色化學原則開發新穎合成方法，合成出具有生物活性骨架的化合物。
首先，我們使用3-亞烷基吲哚酮和靛紅在符合綠色化學的條件下使用分子篩進行直接的插烯羥醛反應，成功合成出具有各種不同取代基之3,3-雙取代吲哚酮骨架的產物，具有良好的產率。
再來，我們使用β-酮酸和對甲基醌在只有使用氟化醇類作為溶劑，且沒有使用鹼和催化劑的條件下進行去羧基化之1,6共軛加成反應 ，成功合成出具有各種不同取代基之雙芳香環甲烷骨架的產物，具有良好的產率 。

The primary concern of this study is developing novel synthetic methods to synthesize compounds with bioactive frameworks based on green chemistry principles.
First, we developed a direct vinylogous aldol reaction of 3-alkylidene oxindoles with isatins using molecular sieve. We constructed the products with 3,3-disubstituted oxindoles frameworks successfully in high yields (up to 98% yield).
Next, we also developed a decarboxylative 1,6-conjugate addition reaction of β-keto acids and p-quinone methides. We only used fluorinated alcohols as solvent without bases and catalysts to construct the products with diarylmethanes frameworks successfully in high yields (up to 99% yield).

摘要
Abstract
目錄
圖目錄
表目錄
流程圖目錄
縮寫用語對照表
第一章、開發以綠色化學為原則的方法學
1.1綠色化學介紹
1.1.1綠色化學隨著時代的演變1
1.2 利用分子篩進行3-亞烷基吲哚酮 (3-alkylidene oxindoles)與靛紅 (isatin) 之插烯羥醛反應介紹
1.2.1 插烯反應
1.2.2 直接插烯羥醛反應
1.2.3 利用分子篩進行3-亞烷基吲哚酮與靛紅之插烯羥醛反應研究動機
1.3 利用氟化醇類進行對甲基醌和β - 酮酸去羧基化1,6共軛加成反應
1.3.1 氟化醇類 (fluorinated alcohols)介紹
1.3.2 氟化醇類的特殊物理和化學性質
1.3.2 多芳香基甲烷化合物介紹
1.3.3 1,6共軛加成反應介紹
1.3.4 去羧基化反應介紹
1.3.5 利用氟化醇類進行對甲基醌和β -酮酸去羧基化之1,6共軛加成反應研究動機
第二章、結果與討論
2.1 利用分子篩進行3-亞烷基吲哚酮與靛紅之插烯羥醛反應的起始物製備
2.1.1 親核性試劑3-亞烷基吲哚酮 (1a-1g)的製備
2.1.2 利用分子篩進行3-亞烷基吲哚酮與靛紅之插烯羥醛反應的條件最佳化篩選
2.1.3 利用分子篩進行3-亞烷基吲哚酮與靛紅之插烯羥醛反應的通用性測試 (substrate scope)
2.1.4 結構鑑定
2.1.5 分子篩回收再使用實驗
2.1.6控制組實驗
2.2 利用氟化醇類進行對甲基醌和β -酮酸去羧基化之1,6共軛加成反應
2.2.1 起始物親核性試劑β-酮酸製備
2.2.2 起始物親電子性試劑對甲基醌製備
2.2.3 利用氟化醇類進行對甲基醌和β -酮酸去羧基化之1,6共軛加成反應條件最佳化篩選
利用氟化醇類進行對甲基醌和β -酮酸去羧基化之1,6共軛加成的通用性測試 (substrate scope)
2.2.4 控制組實驗
第三章、結論
3.1利用分子篩進行3-亞烷基吲哚酮與靛紅之插烯羥醛反應結論
3.2利用氟化醇類進行對甲基醌和β -酮酸去羧基化之1,6共軛加成反應結論
第四章、實驗步驟與光譜數據
4.1 一般實驗方法
4.2 實驗步驟與光譜數據
4.2.1起始物親核性試劑3-亞烷基吲哚酮製備
4.2.2 起始物親核性試劑 1a-1c, 1f-1g和親電子性試劑 2a-2h的插烯羥醛反應合成步驟
4.2.3 起始物親核性試劑β-酮酸製備
4.2.4 起始物親電子性試劑對甲基醌製備
4.2.5 起始物親核性試劑β-酮酸13a-13i和親電子性試劑對甲基醌16a-16m之去羧基化1,6-共軛加成反應產物製備
4.2.6 產物光譜數據
第五章、參考文獻
附錄1、氫核磁共振光譜、碳核磁共振光譜、紅外線光譜圖、質譜圖

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