5,11,17,23,29,35-Hexa-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis<(4-methylbenzyl)oxy>calix<6>arene | 140659-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17,23,29,35-Hexa-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis<(4-methylbenzyl)oxy>calix<6>arene
• 英文别名: 1,2,4,5-tetrakis-(p-methylbenzyloxy)calix[6]arene；5,11,17,23,29,35-hexatert-butyl-38,39,41,42-tetrakis[(4-methylphenyl)methoxy]heptacyclo[31.3.1.13,7.19,13.115,19.121,25.127,31]dotetraconta-1(36),3(42),4,6,9,11,13(41),15,17,19(40),21(39),22,24,27,29,31(38),33(37),34-octadecaene-37,40-diol
• CAS: 140659-06-9
• 化学式: C₉₈H₁₁₆O₆
• 分子量: 1390.0
• InChiKey: MAKAEHZLJKJMMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  24.29
• 重原子数：
  104.0
• 可旋转键数：
  12.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  右旋樟脑-10-磺酰氯 、 5,11,17,23,29,35-Hexa-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis<(4-methylbenzyl)oxy>calix<6>arene 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以31%的产率得到(1'S,4'R)-5,11,17,23,29,35-hexa-tert-butyl-39-(camphor-10-sulfonyloxy)-42-hydroxy-37,38,40,41-tetrakis(4-methylbenzyloxy)calix[6]arene
  参考文献：
  名称：

  手性 1,10-菲咯啉桥接杯[6]芳烃

  摘要：

  研究了 1,10-菲咯啉桥接杯 [6] 芳烃 3 手性衍生物的几种方法，并合成了 7 种新的手性杯 [6] 芳烃。C2 对称轴手性双大环 5 已合成为外消旋混合物；使用对映体纯试剂制备了带有手性取代基（樟脑磺酰基、肉豆蔻酰基）的杯芳烃 8、14、18、19、20 和 21。三个手性双大环 5、19 和 20 也已通过 X 射线分析进行了分析。在 CuI 催化的苯乙烯和茚环丙烷化反应中，所有化合物都作为铜离子的配体进行了测试。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200600295
• 作为产物：
  描述：

  4-叔丁基杯[6]芳烃 、 4-甲基苄溴 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<(4-methylbenzyl)oxy>calix<6>arene
  参考文献：
  名称：

  Calixarenes. 29. Aroylation and arylmethylation of calix[6]arenes

  摘要：

  Aroylations and arylmethylations of p-tert-butylcalix[6]arene have been carried out using a variety of parasubstituted aroyl chlorides and arylmethyl halides to determine the effect of para substituents on the structural and/or conformational outcome of the reactions. When an excess of derivatizing agent is used with NaH as the base the products in all cases are the 1,2,4,5-tetrasubstituted compounds in the 1,2,3-alternate conformation. However, with Me3SiOK as the base the products of arylmethylation are the 1,4-diethers. By varying the reaction conditions it is possible in some cases to prepare hexaethers as well as monoethers. By means of H-1 NMR spectral measurements it has been shown that any aroyl moiety or any para-substituted phenylmethyl moiety is large enough to prevent its rotation through the annulus of the calix[6]arene, thus partially, or in some cases completely, freezing the conformation. The unsubstituted benzyl moiety, however, is small enough to pass through the annulus fairly easily, thus allowing complete conformational interconversion to occur. The synthetic utility of these derivatives is adumbrated by the selective de-tert-butylation of a tetraester and the intramolecular bridging of a diether.

  DOI：

  10.1021/jo00037a037

文献信息

• Paraquat guest-induced conformational templation of dicarboxylatocalixarenes
  作者：Teresa Pierro、Carmine Gaeta、Placido Neri

  DOI：10.1080/10610278.2010.500731

  日期：2010.11.1

  Proximal dicarboxylatocalix[4]arene 4 and distal dicarboxylatocalix[6]arene 5 have been synthesised in good yields and their complexation abilities towards dicationic paraquat guest 3 have been studied by NMR spectroscopy. Both hosts are able to complex 3 through an induced-fit mechanism, which originates from the conformational flexibility of calixarene macrocycle. A pH-dependent switching system was realised in which guest inclusion can be controlled through an acid/base external stimulus.