標題: 三烷基鋁作為砜基之切割試劑的固相有機合成研究
Trialkylalumium as Cleavage Reagents for Sulfone Linker in Solid-Phase Organic Synthesis
作者: 廖政二
Cheng-Erh Liao
吳獻仁
鍾文聖
Hsin-Jen Wu
Wen-Sheng Chung
應用化學系碩博士班
關鍵字: 固相有機合成;三烷基鋁;切割試劑;Solid-Phase Organic Synthesis;Cleavage Reagents;Trialkylalumium
公開日期: 2003
摘要: 在液相反應中,我們以benzene sulfinic acid sodium salt為起始物,經歷三個反應步驟,以三烷基鋁為切割試劑,成功的合成出1-(4-Bromophenyl)-2-(4-vinylphenyl)propane與1-(4-Bromophenyl)-2-(4-vinylphenyl)butane;接著,在實驗室中我們成功的製備以砜基為連結元件之樹脂,且應用此砜基樹酯為固相有機合成之載體,並開發三烷基鋁為固相有機合成之切割試劑,順利的合成出21個衍生物的化合物庫。 另外,我們也以砜基樹酯,引進環狀雙烷基取代,並應用三烷基鋁為切割試劑,成功的合成出兩個四環之化合物3-methyl-3-(4-vinylphenyl)cyclobutan-1-ol和3-ethyl-3-(4-vinylphenyl)-cyclobutan-1-ol。
Using sulfinate functionalized resin as a solid support, we have developed a new cleavage reagent, Al(CH3)3 and Al(CH2CH3)3, In monoalkylation successfully synthesized 1-(4-Bromophenyl)-2-(4-vinylphenyl) propane and 1-(4-Bromophenyl)-2-(4-vinylphenyl) butane; In dialkylation successfully synthesized 3-methyl-3-(4-vinylphenyl) cyclobutan-1-ol and 3-ethyl-3-(4-vinylphenyl) cyclobutan-1-ol First of all, benzene sulfinic acid sodium salt was used as starting material in liquid phase experiment. Through three reaction steps, we obtained compound 4 and 5, which demonstrated that cleavage reagent can be successfully Then, we successfully prepared resin 6 which has sulfone linker. Using resin 6 as solid support in SPOS, similar reaction conditions in liquid phase and Al(CH3)3 and Al(CH2CH3)3 as cleavage reagent, we obtained the products form solid support. Application of SPOS technique, we synthesized compounds which includes 4、5、10、11、13、14、16、17、19、21、22、25、26、28、29、31、32、34、35、37、38、41、42.
URI: http://140.113.39.130/cdrfb3/record/nctu/#GT009125552
http://hdl.handle.net/11536/55090
Appears in Collections:Thesis


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