5,11,17,23,29,35,41,47-octaphenyl-49,50,51,52,53,54,55,56-octahydroxycalix<8>arene | 92887-20-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 5,11,17,23,29,35,41,47-octaphenyl-49,50,51,52,53,54,55,56-octahydroxycalix<8>arene
• 英文别名: 5,11,17,23,29,35,41,47-octaphenyl-49,50,51,52,53,54,55,56-octahydroxycalix[8]arene；p-phenylcalix[8]arene；5,11,17,23,29,35,41,47-Octakis-phenylnonacyclo[43.3.1.13,7.19,13.115,19.121,25.127,31.133,37.139,43]hexapentaconta-1(48),3,5,7(56),9,11,13(55),15,17,19(54),21,23,25(53),27(52),28,30,33(51),34,36,39(50),40,42,45(49),46-tetracosaene-49,50,51,52,53,54,55,56-octol
• CAS: 92887-20-2
• 化学式: C₁₀₄H₈₀O₈
• 分子量: 1457.77
• InChiKey: HABXRDKLFAWHEK-UHFFFAOYSA-N

物化性质

• 熔点：
  421-423 °C
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  25.5
• 重原子数：
  112
• 可旋转键数：
  8
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  162
• 氢给体数：
  8
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,11,17,23,29,35,41,47-octaphenyl-49,50,51,52,53,54,55,56-octahydroxycalix<8>arene 在 硫酸 作用下， 反应 12.0h， 生成 p-(4-sulfonatophenyl)calix[8]arene
  参考文献：
  名称：

  带有延伸臂的杯芳烃的直接合成：对苯杯[4,5,6,8]芳烃及其水溶性磺化衍生物

  摘要：

  已从对苯酚与甲醛在四氢萘中的碱催化缩合中分离出对苯基杯[4,5,6,8]芳烃，并使用硫酸或氯磺酸将其选择性转化为相应的磺化衍生物。

  DOI：

  10.1016/s0040-4039(01)01218-7
• 作为产物：
  描述：

  聚合甲醛 、 对羟基联苯 在 cesium hydroxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 水 为溶剂， 反应 4.0h， 以34%的产率得到5,11,17,23,29,35,41,47-octaphenyl-49,50,51,52,53,54,55,56-octahydroxycalix<8>arene
  参考文献：
  名称：

  Synthesis and in vivo biological activity of large-ringed calixarenes against Mycobacterium tuberculosis

  摘要：

  A series of large-ringed calix[6,7,8]arene analogues have been synthesised and their affect against Mycobacterium tuberculosis in vivo established. In general, when p-phenylcalixarenes and tert-butylcalixarenes were not functionalised at the lower rim, low biological activities were observed. However on going from partially to fully lower rim pegylated calixarenes the anti-mycobacterial properties improved. The addition of cyanopropoxy groups at the lower rim gave rise to low activities, whereas the addition of acetate moieties interestingly had pro-TB effects. Two upper rim sulfonated calixarenes showed promising properties. In the course of this work, a high yielding procedure to synthesise p-phenylcalix[7]arene was also established. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.034

文献信息

• Calixarenes. 16. Functionalized calixarenes: the direct substitution route
  作者：C. David Gutsche、Philip F. Pagoria

  DOI：10.1021/jo00350a071

  日期：1985.12
• GUTSCHE, C. D.;PAGORIA, PH. F., J. ORG. CHEM., 1985, 50, N 26, 5795-5802
  作者：GUTSCHE, C. D.、PAGORIA, PH. F.

  DOI：——

  日期：——
• Synthesis and in vivo biological activity of large-ringed calixarenes against Mycobacterium tuberculosis
  作者：Kerry J. Goodworth、Anne-Cécile Hervé、Evangelos Stavropoulos、Gwénaelle Hervé、Isabel Casades、Alison M. Hill、Gordon G. Weingarten、Ricardo E. Tascon、M. Joseph Colston、Helen C. Hailes

  DOI：10.1016/j.tet.2010.11.034

  日期：2011.1

  A series of large-ringed calix[6,7,8]arene analogues have been synthesised and their affect against Mycobacterium tuberculosis in vivo established. In general, when p-phenylcalixarenes and tert-butylcalixarenes were not functionalised at the lower rim, low biological activities were observed. However on going from partially to fully lower rim pegylated calixarenes the anti-mycobacterial properties improved. The addition of cyanopropoxy groups at the lower rim gave rise to low activities, whereas the addition of acetate moieties interestingly had pro-TB effects. Two upper rim sulfonated calixarenes showed promising properties. In the course of this work, a high yielding procedure to synthesise p-phenylcalix[7]arene was also established. (C) 2010 Elsevier Ltd. All rights reserved.
• Direct synthesis of calixarenes with extended arms: p-phenylcalix[4,5,6,8]arenes and their water-soluble sulfonated derivatives
  作者：Mohamed Makha、Colin L Raston

  DOI：10.1016/s0040-4039(01)01218-7

  日期：2001.8

  p-Phenylcalix[4,5,6,8]arenes have been isolated from the base catalysed condensation of p-phenylphenol with formaldehyde in tetralin, and selectively converted to the corresponding sulfonated derivatives using sulfuric or chlorosulfonic acids.

  已从对苯酚与甲醛在四氢萘中的碱催化缩合中分离出对苯基杯[4,5,6,8]芳烃，并使用硫酸或氯磺酸将其选择性转化为相应的磺化衍生物。