5,11,17,23,29,35-Hexa-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis<(4-cyanobenzyl)oxy>calix<6>arene | 140659-08-1

• 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-cyanobenzyl)oxy>calix<6>arene
• 英文别名: 4-[[5,11,17,23,29,35-hexatert-butyl-38,40,41-tris[(4-cyanophenyl)methoxy]-39,42-dihydroxy-37-heptacyclo[31.3.1.13,7.19,13.115,19.121,25.127,31]dotetraconta-1(37),3,5,7(42),9(41),10,12,15,17,19(40),21(39),22,24,27(38),28,30,33,35-octadecaenyl]oxymethyl]benzonitrile
• CAS: 140659-08-1
• 化学式: C₉₈H₁₀₄N₄O₆
• 分子量: 1433.93
• InChiKey: YBKONRRVGFAMDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.54
• 重原子数：
  108.0
• 可旋转键数：
  12.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  172.54
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  4-叔丁基杯[6]芳烃 、 对氰基溴化苄 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-cyanobenzyl)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