四烷基间苯二酚杯芳烃八[N-(2-吡啶甲基)乙酰胺]的合成和分子结构

doi:10.11944/j.issn.1000-0518.2015.12.150206

摘要/Abstract

摘要：

为深入开展杯芳烃为骨架的超分子拓扑结构的组装和性能,开展了间苯二酚杯芳烃八取代吡啶酰胺的合成和分子结构的研究。以四丙基、四己基和四庚基间苯二酚杯芳烃为原料,使用α-氯乙酸甲酯实现O-烃基化,后者在无溶剂条件下与2-氨甲基吡啶反应实现酰胺化,制备了烷基间苯二酚杯芳烃八[N-(2-吡啶甲基)乙酰胺]衍生物。用X衍射方法测定了四丙基间苯二酚杯芳烃八乙酸甲酯、四丙基以及四己基间苯二酚杯芳烃八[N-(2-吡啶甲基)乙酰胺]的单晶分子结构。在晶体中,间苯二酚杯芳烃都以全顺式构型存在,在成环的四个间苯二酚单元中,1,3-位的两个间苯二酚单元处于近直立构象,2,4-位的另两个间苯二酚单元处于近平伏构象,而4个烷基皆处于分子的下缘,8个乙酰胺支链伸向分子的外围。

关键词: 大环化合物, 间苯二酚杯芳烃, 吡啶, 晶体结构, 分子构型

Abstract:

In order to deeply investigate the assembly and function of supramolecular topological structures based on the skeleton of carlixarenes, we launched the study on the synthesis and molecular structures of resorcinarene octasubstituted pyridymethylacetamides. A series of tetraalkyl resorcinarene octa[N-(2-pyridylmethyl)acetamides] was prepared by sequential alkylation of resorcinarene with methyl α-chloroacetate and ammonolysis of the corresponding resorcinarene octaacetates with 2-aminomethylpyridine. Single crystal structures of tetrapropyl resorcinarene acetate, tetrapropyl and tetrahexyl resorcinarene octa(N-2-pyridylmethylacetamides) obtained by X-ray diffraction method indicate that the resorcinarene core adopts rccc(all cis) conformation with two resorcinol rings almost perpendicular to the other two resorcinol rings, four alkyl groups stretching to the lower rim and octa[N-(2-pyridylmethyl)acetamides] groups stretching outside.

Key words: macrocyclic compound, resorcinarene, pyridine, crystal structure, molecular configuration

穆华荣, 姚勇, 颜朝国. 四烷基间苯二酚杯芳烃八[N-(2-吡啶甲基)乙酰胺]的合成和分子结构[J]. 应用化学, 2015, 32(12): 1416-1422.

MU Huarong, YAO Yong, YAN Chaoguo. Synthesis and Crystal Structure of Tetraalkyl Resorcinarene Octa[N-(2-pyridylmethyl)acetamides][J]. Chinese Journal of Applied Chemistry, 2015, 32(12): 1416-1422.

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