4-(4-nitrobenzylideneamino)-2,6-diphenylphenol | 1263417-95-3

• 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: 4-(4-nitrobenzylideneamino)-2,6-diphenylphenol
• 英文别名: 4-[(4-Nitrophenyl)methylideneamino]-2,6-diphenylphenol；4-[(4-nitrophenyl)methylideneamino]-2,6-diphenylphenol
• CAS: 1263417-95-3
• 化学式: C₂₅H₁₈N₂O₃
• 分子量: 394.43
• InChiKey: FQELGSQWHVUXIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-nitrobenzylideneamino)-2,6-diphenylphenol 在 四丁基氢氧化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 C₂₅H₁₇N₂O₃^(1-)
  参考文献：
  名称：

  Nitro-Substituted 4-[(Phenylmethylene)imino]phenolates: Solvatochromism and Their Use as Solvatochromic Switches and as Probes for the Investigation of Preferential Solvation in Solvent Mixtures

  摘要：

  Four 4-[[(4-nitrophenyl)methylene]imino]phenols (2a-d) were synthesized. After deprotonation in solution, they formed the solvatochromic phenolates 3a-d, which revealed a reversal in solvatochromism. Their UV-vis spectroscopic behavior was explained on the basis of the interaction Of the dyes with the medium through combined effects, such as nonspecific solute-solvent interactions and hydrogen bonding between the solvents and the nitro and phenolate groups. Dyes 3a-c were used as probes to investigate binary solvent mixtures, and the synergistic behavior observed was attributed to solvent-solvent and solute-solvent interactions. A very unusual UV-vis spectroscopic behavior occurred with dye 3d, which has in its molecular structure two nitro substituents as acceptor groups and two phenyl groups on the phenolate moiety. In alcohol/water mixtures, the E-T(3d) values increase from pure alcohol (methanol, ethanol, and propan-2-ol) until the addition of up to 80-96% Water. Subsequently, the addition of a small amount of water causes a very sharp reduction in the E-T(3d) value (for methanol, this corresponds to a bathochromic shift from 543 to 732 nm). This represents the first example of a solvatochromic switch triggered by a subtle change in the polarity of the medium, the color of the solutions being easily reversed by adding small amounts of the required cosolvent.

  DOI：

  10.1021/jo301890r
• 作为产物：
  描述：

  4-氨基-2,6-二苯基苯酚 、 对硝基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以16%的产率得到4-(4-nitrobenzylideneamino)-2,6-diphenylphenol
  参考文献：
  名称：

  基于 4-(4-硝基亚苄基胺)-2,6-二苯基苯酚的阴离子显色化学传感器用于选择性检测乙腈-水混合物中的氰化物

  摘要：

  Nitrobenzylideneamine)-2,6-diphenylphenol 3a 被合成并作为阴离子显色化学传感器进行研究。3a 在乙腈中的溶液是无色的，但在去质子化作用下会变成蓝色。从添加到 3a 溶液中的各种阴离子中，只有 CN - 、F - 以及强度较低的 CH3COO - 和 H2PO4 - 导致溶液有色。添加高达 2.4% (v/v) 的水后，在所有使用的阴离子中，仅 CN - 能够充当碱并导致溶液颜色发生变化。基于两种 3a:阴离子化学计量比，1:1 和 1:2，使用模型来解释结果。

  DOI：

  10.3998/ark.5550190.0011.b13