39,42-Dihydroxy-37,38,40,41-tetrakis(benzoyloxy)calix<6>arene | 140149-05-9

• 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: 39,42-Dihydroxy-37,38,40,41-tetrakis(benzoyloxy)calix<6>arene
• CAS: 140149-05-9
• 化学式: C₇₀H₅₂O₁₀
• 分子量: 1053.18
• InChiKey: UNMQWPFZTZLSCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.5
• 重原子数：
  80
• 可旋转键数：
  12
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  冠6烯 、 苯甲酰氯 在 sodium hydride 作用下， 生成 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