3-tetradecyl-1-p-tolyl-pyrrole-2,5-dione | 887144-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-tetradecyl-1-p-tolyl-pyrrole-2,5-dione
• 英文别名: 1-(4-Methylphenyl)-3-tetradecylpyrrole-2,5-dione；1-(4-methylphenyl)-3-tetradecylpyrrole-2,5-dione
• CAS: 887144-80-1
• 化学式: C₂₅H₃₇NO₂
• 分子量: 383.574
• InChiKey: JEEJPCKDHBYNCL-UHFFFAOYSA-N

物化性质

• 熔点：
  72-74 °C(Solv: ligroine (8032-32-4); ethyl acetate (141-78-6))
• 沸点：
  506.3±29.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-tetradecyl-1-p-tolyl-pyrrole-2,5-dione 在 溶剂黄146 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 66.0h， 生成 3,4-ditetradecyl-1-p-tolyl-pyrrole-2,5-dione
  参考文献：
  名称：

  Haval–Argade contrathermodynamic rearrangement of alkylidenesuccinimides to alkylmaleimides via the corresponding isoimides: a general approach to alkyl and dialkyl substituted maleimides

  摘要：

  A simple and efficient access to alkyl and dialkyl substituted maleimides has been demonstrated via the new contrathermodynamic rearrangement of (E)-alkylidenesuccinimides to alkylinaleimides. The (E)-alkylidenesuccinimides obtained from the Wittig-condensation of N-arylmaleimide with aliphatic aldehydes oil regioselective hydrolysis furnished the corresponding (E)-alkylidenesuccinanilic acids in 95-98% yields. The beta-alkylidenesuccinanilic acids oil treatment with cyanuric chloride in the presence of triethylamine gave the corresponding beta-alkylisomaleimides in 78-80% yields via the beta-alkylideneisosuccinimides with the exocyclic to endocyclic carbon-carbon double bond migration. The kinetically controlled products alkylisomaleimides in refluxing acetic acid furnished the thermodynamically controlled alkylinaleimides in 98% yield. The Wittig condensation of alkyl substituted isomaleimides/maleimides with aliphatic aldehydes gave the desired dialkyl substituted maleimides in high yields. A conversion of alpha-methylenesuccinanilic acids to alpha-methylisomaleimides has also been described, with 90% yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.091
• 作为产物：
  描述：

  1-(4-甲基苯基)-1H-吡咯-2,5-二酮 在 lithium hydroxide 、 三聚氯氰 、 溶剂黄146 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 15.5h， 生成 3-tetradecyl-1-p-tolyl-pyrrole-2,5-dione
  参考文献：
  名称：

  Haval–Argade contrathermodynamic rearrangement of alkylidenesuccinimides to alkylmaleimides via the corresponding isoimides: a general approach to alkyl and dialkyl substituted maleimides

  摘要：

  A simple and efficient access to alkyl and dialkyl substituted maleimides has been demonstrated via the new contrathermodynamic rearrangement of (E)-alkylidenesuccinimides to alkylinaleimides. The (E)-alkylidenesuccinimides obtained from the Wittig-condensation of N-arylmaleimide with aliphatic aldehydes oil regioselective hydrolysis furnished the corresponding (E)-alkylidenesuccinanilic acids in 95-98% yields. The beta-alkylidenesuccinanilic acids oil treatment with cyanuric chloride in the presence of triethylamine gave the corresponding beta-alkylisomaleimides in 78-80% yields via the beta-alkylideneisosuccinimides with the exocyclic to endocyclic carbon-carbon double bond migration. The kinetically controlled products alkylisomaleimides in refluxing acetic acid furnished the thermodynamically controlled alkylinaleimides in 98% yield. The Wittig condensation of alkyl substituted isomaleimides/maleimides with aliphatic aldehydes gave the desired dialkyl substituted maleimides in high yields. A conversion of alpha-methylenesuccinanilic acids to alpha-methylisomaleimides has also been described, with 90% yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.091

文献信息

• Haval–Argade contrathermodynamic rearrangement of alkylidenesuccinimides to alkylmaleimides via the corresponding isoimides: a general approach to alkyl and dialkyl substituted maleimides
  作者：Kishan P. Haval、Narshinha P. Argade

  DOI：10.1016/j.tet.2006.01.091

  日期：2006.4

  A simple and efficient access to alkyl and dialkyl substituted maleimides has been demonstrated via the new contrathermodynamic rearrangement of (E)-alkylidenesuccinimides to alkylinaleimides. The (E)-alkylidenesuccinimides obtained from the Wittig-condensation of N-arylmaleimide with aliphatic aldehydes oil regioselective hydrolysis furnished the corresponding (E)-alkylidenesuccinanilic acids in 95-98% yields. The beta-alkylidenesuccinanilic acids oil treatment with cyanuric chloride in the presence of triethylamine gave the corresponding beta-alkylisomaleimides in 78-80% yields via the beta-alkylideneisosuccinimides with the exocyclic to endocyclic carbon-carbon double bond migration. The kinetically controlled products alkylisomaleimides in refluxing acetic acid furnished the thermodynamically controlled alkylinaleimides in 98% yield. The Wittig condensation of alkyl substituted isomaleimides/maleimides with aliphatic aldehydes gave the desired dialkyl substituted maleimides in high yields. A conversion of alpha-methylenesuccinanilic acids to alpha-methylisomaleimides has also been described, with 90% yield. (c) 2006 Elsevier Ltd. All rights reserved.