bis(3,4-dichlorophenyl)-3-pyridylmethane

• 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: bis(3,4-dichlorophenyl)-3-pyridylmethane
• 英文别名: 3-[Bis(3,4-dichlorophenyl)methyl]pyridine
• 化学式: C₁₈H₁₁Cl₄N
• 分子量: 383.104
• InChiKey: RYVFCRZKQXKODI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-吡啶甲醛 、 邻二氯苯 在 三氟甲磺酸 作用下， 反应 12.0h， 以87%的产率得到bis(3,4-dichlorophenyl)-3-pyridylmethane
  参考文献：
  名称：

  3-Pyridinecarboxaldehyde:  A Model System for Superelectrophilic Activation and the Observation of a Diprotonated Electrophile

  摘要：

  3-Pyridinecarboxaldehyde (7) has been studied as a model system for superelectrophilic activation. When compound 7 is compared with benzaldehyde (3) in acid-catalyzed condensation reactions with arenes, 7 is more reactive than 3. Compound 7 reacts with chlorobenzene, o-dichlorobenzene, or nitrobenzene in CF3SO3H (triflic acid, TfOH) to give diaryl-3-pyridylmethanes, while 3 does not react with these deactivated arenes in TfOH. Moreover, 7 reacts with benzene in solutions as weakly acidic as H-o = -9, while 3 requires acidity in the range of H-o = -11.5 to -14 to reach a comparable level of electrophilic reactivity. Compound 7 was studied in acidic solution by C-13 NMR, and the diprotonated, dicationic species was observed at -60 degrees C in a solution of FSO3H-SbF5.

  DOI：

  10.1021/jo9824908

文献信息

• 3-Pyridinecarboxaldehyde:  A Model System for Superelectrophilic Activation and the Observation of a Diprotonated Electrophile
  作者：Douglas A. Klumpp、Siufu Lau

  DOI：10.1021/jo9824908

  日期：1999.10.1

  3-Pyridinecarboxaldehyde (7) has been studied as a model system for superelectrophilic activation. When compound 7 is compared with benzaldehyde (3) in acid-catalyzed condensation reactions with arenes, 7 is more reactive than 3. Compound 7 reacts with chlorobenzene, o-dichlorobenzene, or nitrobenzene in CF3SO3H (triflic acid, TfOH) to give diaryl-3-pyridylmethanes, while 3 does not react with these deactivated arenes in TfOH. Moreover, 7 reacts with benzene in solutions as weakly acidic as H-o = -9, while 3 requires acidity in the range of H-o = -11.5 to -14 to reach a comparable level of electrophilic reactivity. Compound 7 was studied in acidic solution by C-13 NMR, and the diprotonated, dicationic species was observed at -60 degrees C in a solution of FSO3H-SbF5.
• Superacid-promoted reactions of pyrazolecarboxaldehydes and the role of dicationic electrophiles
  作者：Douglas A. Klumpp、Patrick J. Kindelin、Ang Li

  DOI：10.1016/j.tetlet.2005.02.152

  日期：2005.4

  Pyrazolecarboxaldehydes react in the Bronsted superacid triflic acid (CF3SO3H, TfOH) to generate electrophilic intermediates capable of reacting with benzene in condensation reactions. Appropriately substituted pyrazoles may also undergo intramolecular Friedel-Crafts-type reactions. It is proposed that the pyrazolecarboxaldehydes and related systems form diprotonated intermediates in these reactions. (c) 2005 Elsevier Ltd. All rights reserved.