25,28-[anthraquinone-1,8-diyldioxydi(ethyleneoxy)]5,11,17,23-tetra-tert-butyl-26,28-dihydroxycalixarene | 166903-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 25,28-[anthraquinone-1,8-diyldioxydi(ethyleneoxy)]5,11,17,23-tetra-tert-butyl-26,28-dihydroxycalixarene
• CAS: 166903-27-1
• 化学式: C₆₂H₆₈O₈
• 分子量: 941.217
• InChiKey: FVKOFHMVLNCDIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.97
• 重原子数：
  70.0
• 可旋转键数：
  0.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  111.52
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  溴乙酸乙酯 、 25,28-[anthraquinone-1,8-diyldioxydi(ethyleneoxy)]5,11,17,23-tetra-tert-butyl-26,28-dihydroxycalixarene 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到25,27-[anthraquinone-1,8-diyldioxydi(ethyleneoxy)]-5,11,17,23-tetra-tert-butyl-26,28-di(ethoxycarbonylmethoxy)calixarene
  参考文献：
  名称：

  Selectivity in redox-switched calix[4]arene cationophores: electrochemical detection of a conformational change on cation binding

  摘要：

  三个4-叔丁基杯[4]芳烃在交替的酚氧原子之间带有1,8-双（乙烯氧基）蒽醌桥，在单电子还原下，显示出碱金属阳离子具有增强的结合力，选择性取决于连接在另一个酚氧上的基团；对于其中一种化合物，钾的结合伴随着杯芳烃从锥形到部分锥形的构象变化，而钠则没有。

  DOI：

  10.1039/c39950000675
• 作为产物：
  描述：

  1,8-二羟基蒽醌 在 sodium carbonate 、 caesium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 25,28-[anthraquinone-1,8-diyldioxydi(ethyleneoxy)]5,11,17,23-tetra-tert-butyl-26,28-dihydroxycalixarene
  参考文献：
  名称：

  Dynamic Factors in the Design of Redox-switched Calix[4]arene Cationophores.

  摘要：

  Syntheses are described of four calix [4] arenes, each bearing a 9,10-anthraquinone moiety as a redox switch to modify cation binding. The first compound, having a triester-amide lariat-type structure, showed no experimental evidence (from cyclic voltammetry in acetonitrile solution) for enhancement of binding of alkalimetal cations, indicating negligible interaction between the binding site and the switchable group. Computer modelling showed that a large steric barrier prevents rotation of the switch into the energetically favourable position that would enhance cation binding. Compounds in which the anthraquinone formed part of a 1,3-bridging unit spanning the lower rim of the calix showed large cation-binding enhancements, the values being affected by the other, auxiliary groups on the lower rim of the calixarene. Unusual CV behaviour was observed in the case of the compound with two methoxy auxiliary donor groups in the presence of K+, but not with Na+. Computer meddling and NMR spectroscopic evidence indicates that this effect Is attributable to a slow change of the calixarene from a cone to a partial cone conformation in binding K+, whereas the smaller Na+ fits easily into the available cavity of the cone conformation.

  DOI：

  10.3891/acta.chem.scand.52-0407