| 研究生: |
莊孟榕 Chuang, Meng-Jung |
|---|---|
| 論文名稱: |
多組成反應的應用:不對稱鹼的合成 The Application of MCRs(Multicomponent Reactions):The Synthesis of Chiral Base |
| 指導教授: |
宋光生
Sung, Kuangsen |
| 學位類別: |
碩士 Master |
| 系所名稱: |
理學院 - 化學系 Department of Chemistry |
| 論文出版年: | 2002 |
| 畢業學年度: | 90 |
| 語文別: | 中文 |
| 論文頁數: | 66 |
| 中文關鍵詞: | 多組成反應 、不對稱鹼 、異 |
| 外文關鍵詞: | isocyanide, chiral base, Multicomponent Reactions(MCRs) |
| 相關次數: | 點閱:72 下載:1 |
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摘要
由多組成反應的簡介,我們可以了解到多組成反應提供了一種新的合成策略,多反應物的系統變化性,取代基的改變的多樣化以及雙官能基的應用等,我們可以利用這些優點,設計出各式各樣我們所需要的化合物,最重要的是,多組成反應為one-pot reaction,這可以省去很多在反應的過程中我們加藥及處理的步驟。
本研究最大的重點就是,以Ugi的四反應物系統(U-4CR)為藍圖來設計一個實驗,利用反應中間產物為六圓環的特性,在沒有不對稱試劑的系統之下,我們可以在一個已固定不對稱中心的胺基酸身上,再合成另外一個不對稱中心,而這個反應具有高度的立體選擇性。經由化合物的單晶X-ray繞射,我們可以更加確定生成物最主要的空間結構,也可以更加證實我們所預測反應機構的可靠性。
對於本反應的生成物,是屬於胺基兩旁接有兩個不對稱中心的不對稱鹼,在一些文獻上有指出關於某些不對稱鹼可以選擇性辨識兩個對稱而環境一樣的氫,本篇論文僅止於不對稱鹼的合成及簡單的探討。另外,在使用乙和水的混合溶劑系統中,我們意外的發現,我們可以在纈氨酸的氮上接上一個選擇性很高的不對稱中心。
Abstract
According to the introduction of multicomponent reactions, we can know that the multicomponent reactions supply a new synthetic stratagem. Via variability of the systems having many reagents, variability of alterable substitutes and application of the difunction group, we can utilize these merits to plot many kinds of compounds which we want to get. The most important point is that the multicomponent reactions are one-pot reactions, which we can abridge many steps which we add reagents and handle in the reactive process.
The focal point of my study is that I work out a experiment using a blueprint which is based on the Ugi`s four-reagents system (U-4CR). Utilizing the characteristics which the intermediate of reaction is the six-ring, under the systems of achiral reagents, we can synthesize another chiral center on the amino acid which we have fixed a chiral center on it. This reaction is highly stereo-seletive. Via crystal X-ray chart of compound, we can definite the main space-structure of the product. We also can confirm the reliable of reactive mechanism which we have expected.
With regard to the products of this reaction, we belong them to the chiral base which is linked two chiral centers on two sides of the amino group. Some records point out that some chiral bases can selectively discriminate two hydrogens which are symmetry and are in the same environment. This thesis have only the synthesis of the chiral bases and simple investigate. In addition, in the system of mixed solvent of acetoniltrile and water, we unexpectedly discover that we can link a chiral center whose selection is very high on the nitrogen of the valine.
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