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Cylindrical macrocyclic compounds synthesized by connecting two bowl-shaped calix[3]aramide moieties: structures and chiroptical properties

机译:通过连接两个碗状的杯子[3]芳酰胺部分:结构和毛细光学性能合成圆柱形大环化合物

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摘要

Calix[3]aramide-based macrocycles1were successfully synthesized by a Glaser coupling reaction of twometa-calix[3]aramide moieties that have three ethynyl groups. The obtained macrocycles have stereoisomers: an enantiomeric pair and amesoform based on a combination of amide bond directions in the calix[3]aramide moieties at both ends of the molecule. Characteristic absorption spectra derived from the 1,4-diphenylbutadiyne structure were observed, while their ECD spectra were mirror-images. Single-crystal X-ray analysis revealed that each stereoisomer had a cylindrical rigid shape, and the absolute structure of the chiral-form was also assigned by comparing the Flack parameters. Mirror-image VCD spectra were observed for the enantiomeric chiral forms, and a VCD signal pattern of one enantiomer corresponded to that predicted by the relationship between the dihedral angle of the pair of CO groups.
机译:CALIX [3]基于芳酰胺基的宏γ1,通过TWOFTA-CALIX [3]芳酰胺部分具有三种乙炔基的GLASER偶联反应成功地合成。 所得宏依克具有立体异构体:基于分子两端的Calix [3]芳酰胺部分中的酰胺键方向的组合的对映体对和氨素染色。 观察到衍生自1,4-二苯基丁霉素结构的特征吸收光谱,而其ECD光谱是镜像。 单晶X射线分析显示,每个立体异构体具有圆柱形刚性形状,并且还通过比较脆皮参数来分配手性形式的绝对结构。 观察到对映体手性形式的镜像VCD光谱,并且一种对映体的VCD信号模式对应于通过该对CO组的二偏角角之间的关系预测的。

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  • 来源
    《RSC Advances》 |2020年第57期|共7页
  • 作者单位

    Toho Univ Fac Pharmaceut Sci 2-2-1 Miyama Funabashi Chiba 2748510 Japan;

    Toho Univ Fac Pharmaceut Sci 2-2-1 Miyama Funabashi Chiba 2748510 Japan;

    Toho Univ Fac Pharmaceut Sci 2-2-1 Miyama Funabashi Chiba 2748510 Japan;

    Toho Univ Fac Pharmaceut Sci 2-2-1 Miyama Funabashi Chiba 2748510 Japan;

    Toho Univ Fac Pharmaceut Sci 2-2-1 Miyama Funabashi Chiba 2748510 Japan;

    Toho Univ Fac Pharmaceut Sci 2-2-1 Miyama Funabashi Chiba 2748510 Japan;

    Toho Univ Fac Pharmaceut Sci 2-2-1 Miyama Funabashi Chiba 2748510 Japan;

    Toho Univ Fac Pharmaceut Sci 2-2-1 Miyama Funabashi Chiba 2748510 Japan;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 化学;
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