1(4),1(6),5(4),5(6)-tetraisopropyl-3(4),3(6),7(4),7(6)-tetranitro-2,4,6,8-tetraoxa-1,3,5,7-tetrabenzenacyclooctaphane | 1186525-66-5

• 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: 1(4),1(6),5(4),5(6)-tetraisopropyl-3(4),3(6),7(4),7(6)-tetranitro-2,4,6,8-tetraoxa-1,3,5,7-tetrabenzenacyclooctaphane
• 英文别名: 4,6,16,18-Tetranitro-10,12,22,24-tetra(propan-2-yl)-2,8,14,20-tetraoxapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene；4,6,16,18-tetranitro-10,12,22,24-tetra(propan-2-yl)-2,8,14,20-tetraoxapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene
• CAS: 1186525-66-5
• 化学式: C₃₆H₃₆N₄O₁₂
• 分子量: 716.701
• InChiKey: REAAFEHHHIQYOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  52
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  236
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  1,5-二氟-2,4-二硝基苯 、 4,6-diisopropylresorcinol 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以40%的产率得到1(4),1(6),5(4),5(6)-tetraisopropyl-3(4),3(6),7(4),7(6)-tetranitro-2,4,6,8-tetraoxa-1,3,5,7-tetrabenzenacyclooctaphane
  参考文献：
  名称：

  The influence of heteroatoms on the conformational properties of heteracalix[4]arenes. Comparison of oxygen-, sulfur-, and nitrogen-bridged [14]metacyclophanes

  摘要：

  Oxygen- and sulfur-bridged calix[4]arenes have been synthesized by the nucleophilic aromatic substitution of 1,5-difluoro-2,4-dinitrobenzene with 4,6-diisopropylresorcinol or 4,6-diisopropyl-1,3-benzene-dithiol. X-ray crystal structure analyses revealed that the oxacalix[4]arene 2 adopts an unsymmetrical 1,3-alternate Conformation and that the dinitrobenzene rings strongly conjugate with the bridging oxy, en atoms. On the other hand, the thiacalix[4]arene 3 adopts a heavily twisted unsymmetrical 1,3-alternate conformation, and the conjugation is very weak. In the H-1 NMR spectrum (CDCl3, 30 degrees C) both compounds display a pair of diastereotopic methyl signals for the isopropyl groups in agreement with the frozen 1,3-alternate conformation on the NMR time scale. The free energies of activation (Delta G(298)(#)) of the macrocyclic inversion for 2 and 3 were determined to be 69.5 kJ mol (1) and 74.9 kJ mol(-1), respectively, by variable temperature NMR spectroscopy. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.111

文献信息

• The influence of heteroatoms on the conformational properties of heteracalix[4]arenes. Comparison of oxygen-, sulfur-, and nitrogen-bridged [14]metacyclophanes
  作者：Yusuke Yasukawa、Kazuhiro Kobayashi、Hisatoshi Konishi

  DOI：10.1016/j.tetlet.2009.06.111

  日期：2009.9

  Oxygen- and sulfur-bridged calix[4]arenes have been synthesized by the nucleophilic aromatic substitution of 1,5-difluoro-2,4-dinitrobenzene with 4,6-diisopropylresorcinol or 4,6-diisopropyl-1,3-benzene-dithiol. X-ray crystal structure analyses revealed that the oxacalix[4]arene 2 adopts an unsymmetrical 1,3-alternate Conformation and that the dinitrobenzene rings strongly conjugate with the bridging oxy, en atoms. On the other hand, the thiacalix[4]arene 3 adopts a heavily twisted unsymmetrical 1,3-alternate conformation, and the conjugation is very weak. In the H-1 NMR spectrum (CDCl3, 30 degrees C) both compounds display a pair of diastereotopic methyl signals for the isopropyl groups in agreement with the frozen 1,3-alternate conformation on the NMR time scale. The free energies of activation (Delta G(298)(#)) of the macrocyclic inversion for 2 and 3 were determined to be 69.5 kJ mol (1) and 74.9 kJ mol(-1), respectively, by variable temperature NMR spectroscopy. (C) 2009 Elsevier Ltd. All rights reserved.