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Synthesis and X-ray structure of a fluorinated 1,1-dialkoxy-3-iminoisoindoline acetal, an elusive phthalocyanine precursor
Tetrahedron ( IF 2.1 ) Pub Date : 2018-05-16 , DOI: 10.1016/j.tet.2018.05.039
Erik N. Carrión , Angela T. Dang , Sergiu M. Gorun

The synthesis of a fluoroalkylated 1,1-dimethoxy-3-iminoisoindoline acetal, the first representative of the halogenated 3-imino-amino-1-acetal class is reported. In contrast to the protio compound, fluoroalkyl groups make the presence of a base unnecessary for its synthesis while stabilizing the amino tautomer as revealed by an X-ray structural analysis - the first atomic-level structural characterization of the 1,1-alkoxy-3-amino(imino) isoindoline scaffold. Dimers present in solid-state are H-bonded and define a motif similar to the stabilizing, reverse wobble one encountered in adenine-cytosine pairs of tRNA. The fluoro acetal forms easily both metallo- and metal-free phthalocyanines, supporting the proposal that acetals might be phthalocyanine intermediates.



中文翻译:

难以捉摸的酞菁前体氟化1,1-二烷氧基-3-亚氨基异二氢吲哚缩醛的合成及X射线结构

报道了卤代3-亚氨基-氨基-1-缩醛类的第一个代表的氟代烷基化的1,1-二甲氧基-3-亚氨基异吲哚啉缩醛的合成。与质子化合物相反,氟烷基使X射线结构分析揭示了它的合成过程中不必要的碱的存在,同时稳定了氨基互变异构体-1,1-烷氧基3的首次原子级结构表征-氨基(亚氨基)异吲哚啉骨架。固态存在的二聚体通过氢键结合,并定义了类似于tRNA腺嘌呤-胞嘧啶对中遇到的稳定,反向摆动的基序。氟代乙缩醛容易形成无金属和无金属的酞菁,支持了缩醛可能是酞菁中间体的建议。

更新日期:2018-05-16
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