从悉尼酮、慕尼黑酮到蒙特利尔酮: 用城市命名的有机化合物
摘要
Compounds named after cities are rarely seen in organic chemistry. Sydnones, münchnones and montréalones are three such interesting examples. These compounds, which were discovered by scientists at University of Sydeny in 1935, at University of München in 1964 and at McGill University in Montréal in 2007, respectively, are all mesoionic five-membered heterocycles. None of them are simple ketones actually, although the suffix “-ones” has been used in their names. For example, the systematic nomenclature of sydnones is 1,2,3-oxadiazolium-5-olate, while münchnones are 1,3-oxadiazolium-5-olate, and montréalones are actually 5-phosphamünchnones. All of these cyclic structures have aromatic characters. The most important common features are, however, that they can all act as 1,3-dipoles to undergo [3+2] cycloaddition to unsaturated bonds, such as alkenes and alkynes. In recent years, there is a growing interest in such compounds, due partly to the new finding of montréalones. In this review, the history for finding of these important compounds and their structural and chemical properties, especially the application in dipolar cycloaddition reactions, will be briefly discussed.