6-(2-ethylhexyloxy)-3-methylbenzene-1,2,4-tricarbonitrile | 381670-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-(2-ethylhexyloxy)-3-methylbenzene-1,2,4-tricarbonitrile
• 英文别名: 6-(2-Ethylhexoxy)-3-methylbenzene-1,2,4-tricarbonitrile
• CAS: 381670-46-8
• 化学式: C₁₈H₂₁N₃O
• 分子量: 295.384
• InChiKey: IBKWABZRIHVOMO-UHFFFAOYSA-N

物化性质

• 沸点：
  473.2±45.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(2-ethylhexyloxy)-3-methylbenzene-1,2,4-tricarbonitrile 、 tetrakis[(4-formylphenoxy)methyl]methane 在 六甲基磷酰三胺 、 potassium tert-butylate 作用下， 以69%的产率得到3-[(4-{2,2-bis[(4-[6,7-dicyano-5-(2-ethylhexyloxy)-3-oxoisoindolinyl]methylphenoxy)methyl]-3-(4-[6,7-dicyano-5-(2-ethylhexyloxy)-3-oxoisoindolinyl]methylphenoxy)propoxy}phenyl)methyl]-6-(2-ethylhexyloxy)-1-oxoisoindoline-4,5-dicarbonitrile
  参考文献：
  名称：

  Synthesis of 3-Substituted Isoindolin-1-ones by Regioselective Cyclization of Nitrile with a Styryl Double Bond

  摘要：

  An efficient preparation of 3-substituted isoindolin-1-one was established via basic condensation of aromatic or aliphatic aldehyde with 6-alkoxy-3-methylbenzene-1,2,4-tricarbonitrile (1) in a one-pot reaction. The key step involved regioselective either hydrolysis or nucleophilic attack of the hydroxide anion to the 2-cyano group followed by 5-exo-trig cyclization with the involvement of the styryl double bond. The structure of isoindolinone and regiochemistry of the cyclization products were proved by spectroscopic methods.

  DOI：

  10.3987/com-01-9212
• 作为产物：
  描述：

  2,3,5,6-四溴-4-甲基苯酚 在 N-甲基吡咯烷酮 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-(2-ethylhexyloxy)-3-methylbenzene-1,2,4-tricarbonitrile
  参考文献：
  名称：

  Synthesis of 3-Substituted Isoindolin-1-ones by Regioselective Cyclization of Nitrile with a Styryl Double Bond

  摘要：

  An efficient preparation of 3-substituted isoindolin-1-one was established via basic condensation of aromatic or aliphatic aldehyde with 6-alkoxy-3-methylbenzene-1,2,4-tricarbonitrile (1) in a one-pot reaction. The key step involved regioselective either hydrolysis or nucleophilic attack of the hydroxide anion to the 2-cyano group followed by 5-exo-trig cyclization with the involvement of the styryl double bond. The structure of isoindolinone and regiochemistry of the cyclization products were proved by spectroscopic methods.

  DOI：

  10.3987/com-01-9212