苄叉丙酮、硒粉和硼氢化钠一锅法构建四氢-2H-硒吡喃衍生物  

One-Pot Synthesis of Tetrahydro-2H-selenopyran Derivatives from Benzalacetones,Elemental Selenium,and Sodium Borohydride

作　　者：陈栋栋 杨旭锋 Chen Dongdong;Yang Xufeng(Department of Chemistry&Chemical Engineering,Lyuliang University,Lvliang,Shanxi 033001)

机构地区：[1]吕梁学院化学化工系,山西吕梁033001

出　　处：《有机化学》2024年第5期1641-1648,共8页Chinese Journal of Organic Chemistry

基　　金：山西省自然科学基金(Nos.20210302124072,202203021222318,202103021223386);山西省高等学校科技创新(No.2021L568)资助项目。

摘　　要：报道了一种以苄叉丙酮、硒粉和硼氢化钠为原料,采用一锅法合成一系列四氢-2H-硒吡喃衍生物的新方法.此反应通过形成6个新的化学键很好的构建一系列含硒六元环.得到了20个含有四氢-2H-硒吡喃结构的小分子化合物,最高产率可达91%.X单晶衍射分析表明四氢-2H-硒吡喃六元环与环己烷具有类似的空间立体结构,呈现出稳定的椅式构象.此反应在克量级规模下依然可以顺利进行.可能的反应机理表明此反应为涉及双Michael加成/二硒键的断裂/Michael加成/Aldol反应的多步串级反应.此方法具有底物适应性强、不使用过度金属催化剂以及反应条件温和的特点.A reaction has been developed to synthesize a series of tetrahydro-2H-selenopyran derivatives from benzalacetones,sodium borohydride,and elemental selenium by one-pot method.The reaction proceeds well to construct a tetrahydro-2H-selenopyran ring and six new bonds.Twenty tetrahydro-2H-selenopyran derivatives were obtained,and the yield was up to 91%.The X-ray single crystal analysis showed that this selenium-containing heterocyclic ring exists as a stable chair conformation similar to cyclohexane.The reaction works well when scaled up to the gram scale.A possible mechanism was proposed,involving hydrogenation of selenium/double Michael addition/cleavage of diselenide bond/Michael addition/Aldol reaction.This reaction is characterized by high compatibility to substrates,transition-metal free,and mild reaction conditions.

关 键 词：四氢-2H-硒吡喃 环化 硒 一锅法 苄叉丙酮 

分 类 号：O626[理学—有机化学]