5,11-diformyl-25,26,27,28-tetrakis(2-ethoxyethoxy)calix[4]arene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,11-diformyl-25,26,27,28-tetrakis(2-ethoxyethoxy)calix[4]arene
• 英文别名: 25,26,27,28-Tetrakis(2-ethoxyethoxy)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9,11,13(27),15,17,19(26),21(25),22-dodecaene-5,11-dicarbaldehyde
• 化学式: C₄₆H₅₆O₁₀
• 分子量: 768.945
• InChiKey: AVXRUSZRYAFANJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  56
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  25,26,27,28-tetra(ethoxyethoxy)-calix[4]arene 在 乙酸酐 、 四氯化锡 、 二甲基亚砜 作用下， 以 氯仿 为溶剂， 反应 24.5h， 生成 5,11-diformyl-25,26,27,28-tetrakis(2-ethoxyethoxy)calix[4]arene
  参考文献：
  名称：

  The first synthesis and characterisation of elusive cone 1,2-diformyl tetralkoxycalix[4]arenes and their derivatives

  摘要：

  The synthesis and isolation of elusive tetralkoxycalix[4]arenes 2 in the cone conformation and bearing two formyl groups in proximal (1.2) positions at the upper rim are described for the first time. They were obtained as a mixture with the distal (1,3) regioisomers 3 by optimizing the Gross formylation reaction on the tetralkoxycalix[4]arenes 1. After reduction to the corresponding alcohols, compounds 4 could be isolated and oxidized to 1,2-diformyl (2) and 1,2-diacid (6) tetralkoxycalix[4]arenes. These 1,2-difunctionalized derivatives are useful intermediates for the synthesis of calixarene-based molecular receptors having proximal binding groups. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00808-1

文献信息

• Highly efficient intramolecular Cannizzaro reaction between 1,3-distal formyl groups at the upper rim of a cone-calix[4]arene
  作者：Marzia Galli、José Augusto Berrocal、Stefano Di Stefano、Roberta Cacciapaglia、Luigi Mandolini、Laura Baldini、Alessandro Casnati、Franco Ugozzoli

  DOI：10.1039/c2ob25458a

  日期：——

  The 1,3-distal cone-calix[4]arene dialdehyde 1 undergoes Cannizzaro disproportionation in the presence of strong base, but its 1,2-vicinal regioisomer 3 and the analogous monoaldehyde 2 are unreactive under the same conditions. The high intramolecular reactivity of the 1,3-distal regioisomer 1 is measured and discussed in terms of Effective Molarity (EM).

  在强碱存在下，1,3-二叉锥-萼[4]炔二甲醛 1 会发生坎尼扎罗歧化反应，但在相同条件下，它的 1,2- 单向生殖异构体 3 和类似的单醛 2 却不发生反应。我们用有效摩尔度（EM）测量并讨论了 1,3-二取代基异构体 1 的高分子内反应性。
• The first synthesis and characterisation of elusive cone 1,2-diformyl tetralkoxycalix[4]arenes and their derivatives
  作者：Andrea Sartori、Alessandro Casnati、Luigi Mandolini、Francesco Sansone、David N Reinhoudt、Rocco Ungaro

  DOI：10.1016/s0040-4020(03)00808-1

  日期：2003.7

  The synthesis and isolation of elusive tetralkoxycalix[4]arenes 2 in the cone conformation and bearing two formyl groups in proximal (1.2) positions at the upper rim are described for the first time. They were obtained as a mixture with the distal (1,3) regioisomers 3 by optimizing the Gross formylation reaction on the tetralkoxycalix[4]arenes 1. After reduction to the corresponding alcohols, compounds 4 could be isolated and oxidized to 1,2-diformyl (2) and 1,2-diacid (6) tetralkoxycalix[4]arenes. These 1,2-difunctionalized derivatives are useful intermediates for the synthesis of calixarene-based molecular receptors having proximal binding groups. (C) 2003 Elsevier Science Ltd. All rights reserved.