硫杂杯-1,3-2,4-氮杂双冠醚的合成与氨基酸配合性能

对叔丁基硫杂杯四酰肼衍生物(2)与邻苯二甲醛发生分子内1+2缩合反应, 合成了首例1,3-交替构象的硫杂杯-1,3-2,4-氮杂双冠醚(3), 产率为65%. 其结构经元素分析、质谱、核磁共振谱等表征证实. 用UV-Vis光谱法和1H NMR谱研究了化合物3与系列α-氨基酸的识别配合性能, 并计算出其配合常数. 结果表明, 主体分子3对所测试的α-氨基酸有较好的配合作用, 主客体分子形成1∶1的配合物.

Synthesis and Amino Acids Complexation Properties of Thiacalix [ 4 ] -1,3-2,4-aza-bis-crowns

Thiacalixarene is an interesting novel member of the calixarene family. Thiacalixcrowns were paid much attention due to their particular structures and excellent complexation capabilities. In this paper, by reacting p-tert-butylthiacalixarene tetrahydrazide derivative 2 with o-phthalaldehyde, the first example of thiacalix-1,3-2,4-aza-bis-crowns with 1,3-alternate conformation was prepared with “1+2” condensation mode in a 65% yield. Its structure was characterized by elemental analysis, ESI-MS, 1H NMR spectrum. Its complexation properties for series of α-amino acids were studied via UV-Vis and 1H NMR spectra. Their high complexing constants suggest novel thiacalixbiscrown 3 possessed excellent comple-xation abilities for tested amino acids. The correlation coefficients and the 1H NMR spectra change of comple-xation experiments indicate that compound 3 formed 1∶1 stoichiometric complex with amino acids.