【作者】 王辉；

【导师】 胥波；

【作者基本信息】 东华大学 ， 有机化学， 2022， 硕士

【摘要】 含有三氟甲基砜官能团的化合物同时具有亲核和亲电两种属性,利用此特性,可以实现脱砜多官能团化反应。由于环丙烷的特殊结构,此类化合物在人类生活的各个方面都得到了广泛的应用。同样,由于氟元素特殊的理化性质,含氟化合物在农业和医药领域中用途广泛。含氟的环丙烷化合物,结合了氟原子和环丙烷各自的优点,在调控化合物分子理化性质和药物分子生理活性等方面具有独特的作用。因而该类化合物具有极其重要的研究意义和应用价值。本论文中利用三氟甲基砜官能团的特殊性质,以简单易得的单氟代三氟甲基苄基砜化合物和α,β-不饱和化合物为原料,通过碱催化的迈克尔加成-环化反应(MIRC反应),开发了一种简便实用的合成氟代环丙烷和环丙烯的方法。反应底物的电子效应对反应效率影响很小,一般都能以良好的收率(60-84%)以及中等的非对映选择性(8:1)得到氟代环丙烷衍生物。此外,反应主要产物的结构通过X-射线单晶衍射得到了确认。更多还原

【Abstract】 Compounds containing trifluoromethyl sulfone functional groups have both nucleophilic and electrophilic properties.Based on these properties,we could achieve multi-functionalization of the conversion of trifluoromethyl sulfones.Cyclopropane compounds have been widely used in medicines due to their unique structure.On the other hand,fluorinated compounds are also used in pesticides and pharmaceuticals due to the special physical and chemical properties of fluorine.As a result,fluorinated cyclopropanes,combining the advantages of fluorine and cyclopropane,are important in modulating the physiological activities of drug molecules.Therefore,fluorinated cyclopropanes have great research significance and application value.In this paper,facile synthesis of cyclopropenes and fluorinated cyclopropanes from readily available alkyl triflones were developed.Our protocol,regardless of electronic effect,gave products in good to excellent yields（60-84%）and moderate diastereoselectivity（8:1）.The mechanism may involve tandem Michael addition of triflones/intramolecular nucleophilic cyclization（elimination of-SO₂CF₃）/elimination of fluoride.The structure of products was confirmed by X-ray diffraction method.更多还原