(E)-3-tetradecylidene-1-p-tolyl-pyrrolidine-2,5-dione | 558480-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (E)-3-tetradecylidene-1-p-tolyl-pyrrolidine-2,5-dione
• 英文别名: (E)-3-tetradecylidene-1-p-tolylpyrrolidine-2,5-dione；N-p-tolyl-3-(E)-tetradecylidenesuccinimide；(3E)-1-(4-methylphenyl)-3-tetradecylidenepyrrolidine-2,5-dione
• CAS: 558480-31-2
• 化学式: C₂₅H₃₇NO₂
• 分子量: 383.574
• InChiKey: MEXQNPNRGGTTNO-PXLXIMEGSA-N

物化性质

• 熔点：
  58-60 °C(Solv: ligroine (8032-32-4))
• 沸点：
  507.3±53.0 °C(Predicted)
• 密度：
  1.040±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  28
• 可旋转键数：
  13
• 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：

  (E)-3-tetradecylidene-1-p-tolyl-pyrrolidine-2,5-dione 在 lithium hydroxide 、 三聚氯氰 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 4-tetradecyl-5-p-tolylimino-5H-furan-2-one
  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 以 四氢呋喃 为溶剂， 反应 10.5h， 生成 (E)-3-tetradecylidene-1-p-tolyl-pyrrolidine-2,5-dione
  参考文献：
  名称：

  Mangaleswaran, Sivaprakasam; Argade, Narshinha P., Synthesis, 2003, # 3, p. 343 - 345

  摘要：

  DOI：

文献信息

• General Strategy for the Synthesis of Natural and Unnatural Dialkylmaleic Anhydrides
  作者：Kishan P. Haval、Narshinha P. Argade

  DOI：10.1021/jo801284r

  日期：2008.9.1

  Starting from alkylidenesuccinimides, a wide range of dialkylmaleic anhydrides have been synthesized via the generation of a carbanion on a succinimide unit and its condensation with various alkyl halides as the key reaction.

  从亚烷基琥珀酰亚胺开始，已经通过在琥珀酰亚胺单元上产生碳负离子并与各种烷基卤化物缩合为关键反应，合成了多种二烷基马来酸酐。
• 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.
• Mangaleswaran, Sivaprakasam; Argade, Narshinha P., Synthesis, 2003, # 3, p. 343 - 345
  作者：Mangaleswaran, Sivaprakasam、Argade, Narshinha P.

  DOI：——

  日期：——