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Structural and morphological aspects of small 3,5-disubstituted isoxazoles
Journal of Fluorine Chemistry ( IF 1.7 ) Pub Date : 2018-04-15 , DOI: 10.1016/j.jfluchem.2018.04.007
Luana D. Lopes , Adailton J. Bortoluzzi , Giacomo Prampolini , Francisco P. dos Santos , Paolo R. Livotto , Aloir A. Merlo

The structural and morphological features of small 3,5-disubstituted isoxazoles/isoxazolines are presented and discussed in the light of thermal analysis by differential scanning calorimetry (DSC), polarized optical microscopy (POM) technique, combined with single crystal X-ray diffraction and molecular modeling. The title compounds obtained were also characterized by 1H, 13C and 19F NMR. Two of the 3,5-diarylisoxazoles reported here contain totally hydrogenated or fluorinated benzene rings on both sides of the heterocycle. Partially hydrogenated and fluorinated molecules were prepared alternating the position of the benzene rings on 3- and 5-position of the isoxazoles. Other isoxazoles were synthesized to compare the influence of fluorine atoms on the transitional properties. They were synthesized in two steps, starting from [3 + 2] 1,3-dipolar cycloaddition reaction of nitrile oxides with alkenes to yield the isoxazolines and subsequent MnO2-oxidation process to reach the final isoxazoles.



中文翻译:

小型3,5-二取代异恶唑的结构和形态学方面

借助差示扫描量热法(DSC),偏振光学显微镜(POM)技术,单晶X射线衍射和热分析技术,对3,5-二取代异恶唑/异恶唑啉小分子的结构和形态特征进行了介绍和讨论。分子建模。获得的标题化合物的特征还在于1 H,13 C和191 H NMR。此处报道的3,5-二芳基异恶唑中的两个在杂环的两侧均含有完全氢化或氟化的苯环。交替苯环在异恶唑的3位和5位上制备部分氢化和氟化的分子。合成了其他异恶唑,以比较氟原子对过渡性能的影响。它们由两步合成,从腈氧化物与烯烃的[3 + 2] 1,3-偶极环加成反应开始,生成异恶唑啉,随后进行MnO 2-氧化过程,直至最终形成异恶唑。

更新日期:2018-04-15
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