11,17,29,35-Tetra-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis<(4-nitrobenzoyl)oxy>calix<6>arene | 142369-13-9

• 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: 11,17,29,35-Tetra-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis<(4-nitrobenzoyl)oxy>calix<6>arene
• 英文别名: 11,17,29,35-Tetra-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis[(4-nitrobenzoyl)oxy]calix[6]arene
• CAS: 142369-13-9
• 化学式: C₈₆H₈₀N₄O₁₈
• 分子量: 1457.6
• InChiKey: SXMIMFBUZGRQBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.66
• 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：
  0.26
• 拓扑面积：
  318.22
• 氢给体数：
  2.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  11,17,29,35-Tetra-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis<(4-nitrobenzoyl)oxy>calix<6>arene 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以93%的产率得到5,11,23,29-tetra-p-tert-butylcalix[6]arene
  参考文献：
  名称：

  Selective Upper Rim Functionalization and Lower Rim Bridge Building with Calix[4]arenes and Calix[6]arenes¹

  摘要：

  Selective upper rim functionalization of calix[6]arenes has been achieved by selective lower rim benzoylation at the 1,2,4,5 positions followed by AlCl3-induced removal of the tert-butyl groups of the unesterified aryl residues and introduction of various functionalities into the vacated para positions, including bromo (5), dialkylamino, (7-11) cyanomethyl (12), and (propargyloxy)methyl (13) groups. Lower rim bridge building has been achieved via oxidative coupling reactions between the aryne moieties of calix[4]arenes and calix[6]arenes in which O-benzyl groups carry one (from 23 and 24) or two (from 25) propargyloxy residues. In the calix[4]arene series both a single-spanned (32) and a double-spanned (33) double-cavity calixarene were obtained. In the calix[6]arene series only a single-spanned double cavity calixarene (36) could be characterized.

  DOI：

  10.1021/jo952054a
• 作为产物：
  描述：

  5,11,17,23,29,35-Hexa-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis<(4-nitrobenzoyl)oxy>calix<6>arene 在 三氯化铝 、 苯酚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到11,17,29,35-Tetra-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis<(4-nitrobenzoyl)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