3-p-tolylcarbamoyl-heptadec-3-enoic acid | 887144-74-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-p-tolylcarbamoyl-heptadec-3-enoic acid
• 英文别名: (E)-3-[(4-methylphenyl)carbamoyl]heptadec-3-enoic acid
• CAS: 887144-74-3
• 化学式: C₂₅H₃₉NO₃
• 分子量: 401.59
• InChiKey: KIHCICPEXAAJOW-PXLXIMEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  29
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-p-tolylcarbamoyl-heptadec-3-enoic acid 在 三聚氯氰 、 溶剂黄146 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 3-tetradecyl-4-tetradecylidene-1-p-tolyl-pyrrolidine-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 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 10.5h， 生成 3-p-tolylcarbamoyl-heptadec-3-enoic acid
  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.