三氯化鐵輔佐螺旋[4.6]十一-8-酮架構的合成

Abstract

本篇論文旨在於利用三氯化鐵輔佐帶有芳香環炔基支鏈的雙環[4.1.0]庚-2-酮化合物進行一連串的擴環、環化及氯化反應形成螺旋[4.6]十一-8-酮的架構。 反應最佳條件是將帶有各種芳香環炔基支鏈的雙環[4.1.0]庚-2-酮化合物以1,2-二溴乙烷作為溶劑，使用1.5 當量的三氯化鐵並加熱至50 ℃可得到(E)-螺旋[4.6]十一-8-酮的架構，產率24-62 %。X-ray 繞射分析證明了環化產物中的烯基為(E)-構型。 Construction of spiro[4.6]undecan-8-ones via iron(III) chloride-promoted tandem ring expansion/cyclization/chlorination of arylalkynyl-tethered bicyclo[4.1.0]heptan-2-ones was demonstrated. Treatment of arylalkynyl-tethered bicyclo[4.1.0]heptan-2-ones with 1.5 equivalents of iron(III) chloride in 1,2-dibromoethane at 50 ℃ afforded spiro[4.6]undecan-8-ones in 24-62 % yield. Structure elucidation of the (E)-form products was achieved by X-ray crystallography.