5,11,17,23,29,35-Hexa-tert-butyl-38,39,41,42-tetrahydroxy-37,40-bis<(4-nitrobenzoyl)oxy>calix<6>arene | 140149-09-3

• 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-38,39,41,42-tetrahydroxy-37,40-bis<(4-nitrobenzoyl)oxy>calix<6>arene
• 英文别名: [5,11,17,23,29,35-hexatert-butyl-38,39,41,42-tetrahydroxy-40-(4-nitrobenzoyl)oxy-37-heptacyclo[31.3.1.13,7.19,13.115,19.121,25.127,31]dotetraconta-1(36),3,5,7(42),9(41),10,12,15,17,19(40),21,23,25(39),27(38),28,30,33(37),34-octadecaenyl] 4-nitrobenzoate
• CAS: 140149-09-3
• 化学式: C₈₀H₉₀N₂O₁₂
• 分子量: 1271.6
• InChiKey: HLHUIPZUNDCCRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.41
• 重原子数：
  94.0
• 可旋转键数：
  6.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  219.8
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  4-叔丁基杯[6]芳烃 、 4-硝基苯甲酰氯 在 sodium hydride 作用下， 生成 5,11,17,23,29,35-Hexa-tert-butyl-39,40,41,42-tetrahydroxy-37,38-bis<(4-nitrobenzoyl)oxy>calix<6>arene 、 5,11,17,23,29,35-Hexa-tert-butyl-38,39,41,42-tetrahydroxy-37,40-bis<(4-nitrobenzoyl)oxy>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