3-[(2,4-dinitrophenyl)-(5-nitro-1H-indol-3-yl)methyl]-5-nitro-1H-indole | 1275586-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[(2,4-dinitrophenyl)-(5-nitro-1H-indol-3-yl)methyl]-5-nitro-1H-indole
• CAS: 1275586-51-0
• 化学式: C₂₃H₁₄N₆O₈
• 分子量: 502.4
• InChiKey: NRXXXUSYFYBQAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  215
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-[(2,4-dinitrophenyl)-(5-nitro-1H-indol-3-yl)methyl]-5-nitro-1H-indole 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以48%的产率得到3-((2,4-dinitrophenyl)(5-nitro-1H-indol-3-yl)methylene)-5-nitro-3H-indole
  参考文献：
  名称：

  Nitro-substituted 3,3′-bis(indolyl)methane derivatives as anion receptors: Electron-withdrawing effect and tunability of anion binding properties

  摘要：

  A series of nitro-substituted 3,3'-bis-indolyl phenylmethane derivatives were synthesized and their anion binding properties were investigated in detail. The introduction of the electron-withdrawing nitro group into indole unit and/or meso-phenyl ring, which leads to the increased acidity of indole NH and meso-position CH proton, has a positive effect on anion binding. The nitro-substituted bis(indolyl)methane receptors exhibited selective colorimetric sensing of F- anion, as revealed by the notable color and spectral changes, rationally due to the deprotonation of the indole NH of the receptor. Meanwhile, the additive introduction of the nitro substituents on the meso-phenyl ring of bis(indolyl)methane can lead to the deprotonation of the meso-position CH and further induce an irreversible oxidation process obtaining bis(indolyl)methene product in the F- anion sensing system. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2010.12.004
• 作为产物：
  描述：

  2,4-二硝基苯甲醛 、 5-硝基吲哚 在 potassium hydrogensulfate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以62%的产率得到3-[(2,4-dinitrophenyl)-(5-nitro-1H-indol-3-yl)methyl]-5-nitro-1H-indole
  参考文献：
  名称：

  Nitro-substituted 3,3′-bis(indolyl)methane derivatives as anion receptors: Electron-withdrawing effect and tunability of anion binding properties

  摘要：

  A series of nitro-substituted 3,3'-bis-indolyl phenylmethane derivatives were synthesized and their anion binding properties were investigated in detail. The introduction of the electron-withdrawing nitro group into indole unit and/or meso-phenyl ring, which leads to the increased acidity of indole NH and meso-position CH proton, has a positive effect on anion binding. The nitro-substituted bis(indolyl)methane receptors exhibited selective colorimetric sensing of F- anion, as revealed by the notable color and spectral changes, rationally due to the deprotonation of the indole NH of the receptor. Meanwhile, the additive introduction of the nitro substituents on the meso-phenyl ring of bis(indolyl)methane can lead to the deprotonation of the meso-position CH and further induce an irreversible oxidation process obtaining bis(indolyl)methene product in the F- anion sensing system. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2010.12.004

文献信息

• Nitro-substituted 3,3′-bis(indolyl)methane derivatives as anion receptors: Electron-withdrawing effect and tunability of anion binding properties
  作者：Litao Wang、Wei Wei、Yong Guo、Jian Xu、Shijun Shao

  DOI：10.1016/j.saa.2010.12.004

  日期：2011.2

  A series of nitro-substituted 3,3'-bis-indolyl phenylmethane derivatives were synthesized and their anion binding properties were investigated in detail. The introduction of the electron-withdrawing nitro group into indole unit and/or meso-phenyl ring, which leads to the increased acidity of indole NH and meso-position CH proton, has a positive effect on anion binding. The nitro-substituted bis(indolyl)methane receptors exhibited selective colorimetric sensing of F- anion, as revealed by the notable color and spectral changes, rationally due to the deprotonation of the indole NH of the receptor. Meanwhile, the additive introduction of the nitro substituents on the meso-phenyl ring of bis(indolyl)methane can lead to the deprotonation of the meso-position CH and further induce an irreversible oxidation process obtaining bis(indolyl)methene product in the F- anion sensing system. (C) 2010 Elsevier B.V. All rights reserved.