5,11,17,23,29,35-Hexa-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis(benzoyloxy)calix<6>arene | 140149-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,11,17,23,29,35-Hexa-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis(benzoyloxy)calix<6>arene
• 英文别名: 38,39,41,42-tetrabenzoyloxy-5,11,17,23,29,35-hexa-tert-butylcalix<6>arene-37,40-diol
• CAS: 140149-06-0
• 化学式: C₉₄H₁₀₀O₁₀
• 分子量: 1389.82
• InChiKey: TUIUCMMKUOFTCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.62
• 重原子数：
  104.0
• 可旋转键数：
  8.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  145.66
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5,11,17,23,29,35-Hexa-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis(benzoyloxy)calix<6>arene 在 thallium(III) trifluoroacetate 作用下， 以 三氟乙酸 为溶剂， 反应 24.0h， 以80%的产率得到37,38,40,41-tetrabenzoyloxy-11,17,29,35-tetra-tert-butylcalix<6>arene-5,23,39,42-tetrone
  参考文献：
  名称：

  在上部边缘部分官能化的杯[6]芳烃的合成

  摘要：

  报告了在上部边缘选择性功能化的杯[6]芳烃的一些新实例。从在下部边缘被烷基化的杯[6]芳烃1,3,5-三-，1,2,4,5-四-和1,2,3,4,5-五烷基开始，有可能分离出大环化合物2 ，4,6-三-，3,6-二-和6-单官能团在上缘被官能化（18-94％的产率），带有硝基，甲酰基，溴，氯甲基和2-丙烯基。这些部分的修饰允许合成带有氨基，酰胺基，羟甲基，羧基，氰基和氯甲基官能团的大环，这些环可以基于杯[6]芳烃（具有不同的几何结构）用于进一步转化和制备新的分子受体。还报道了六聚大环上的二醌和三醌的实例。

  DOI：

  10.1016/0040-4020(95)00826-t
• 作为产物：
  描述：

  4-叔丁基杯[6]芳烃 、 苯甲酰氯 在 sodium hydride 作用下， 生成 5,11,17,23,29,35-Hexa-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis(benzoyloxy)calix<6>arene
  参考文献：
  名称：

  Calixarenes. 28. Synthesis, structures, and conformations of aroylates of calix[6]arenes

  摘要：

  A study of the aroylation of calix[6]arenes under a variety of conditions has shown that the reaction often yields the 1,2,4,5-tetraester as a major product but that the outcome is dependent both on the aroylating agent and the calixarene. The best results have been obtained with p-nitrobenzoyl chloride which reacts with p-tert-butylcalix[6]arene (1a) to yield a separable mixture containing ca. 40% tetraester 2a and 30% pentaester 3 when NaH is used as the base or up to 85% of the tetraester when 1-methylimidazole is used as the base. In comparable fashion benzoyl chloride and p-nitrobenzoyl chloride react with la and lb, respectively, to yield the tetraesters 2b and 2c, whereas p-allylcalix[6]arene (1c) reacts under the same conditions to produce the hexaester 6. With limiting amounts of p-nitrobenzoylating agent the diesters 4 and 5 have been isolated in low yields. 3,5-Dinitrobenzoyl chloride gives less satisfactory results, producing mixtures containing six or more eaters from which only small amounts of the 1,2,4,5-tetraester 2d have been isolated. The structure and conformation of the products have been established by elemental analysis, mass spectral measurements, and H-1 NMR techniques. In the case of 2a this includes difference NOE and transient NOE determinations which show that the compound exists in a conformation in which two of the aroylated moieties are canted inward so that their p-tert-butyl groups occupy the two faces of the calix[6]arene cavity, thus self-complexing the compound and preventing intermolecular complexation.

  DOI：

  10.1021/jo00037a036