6-hexyloxy-3-methylbenzene-1,2,4-tricarbonitrile | 381670-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-hexyloxy-3-methylbenzene-1,2,4-tricarbonitrile
• 英文别名: 6-Hexoxy-3-methylbenzene-1,2,4-tricarbonitrile
• CAS: 381670-38-8
• 化学式: C₁₆H₁₇N₃O
• 分子量: 267.33
• InChiKey: ZQKZZWDISKEGQV-UHFFFAOYSA-N

物化性质

• 沸点：
  457.4±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  苯甲醛 、 6-hexyloxy-3-methylbenzene-1,2,4-tricarbonitrile 在 六甲基磷酰三胺 、 potassium tert-butylate 作用下， 以61%的产率得到6-hexyloxy-1-oxo-3-benzylisoindoline-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， 反应 16.0h， 生成 6-hexyloxy-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

文献信息

• Synthesis of 3-Substituted Isoindolin-1-ones by Regioselective Cyclization of Nitrile with a Styryl Double Bond
  作者：Fen-Tair Luo、Chin-Hsin Chen

  DOI：10.3987/com-01-9212

  日期：——

  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.