3-decyl-1-(p-tolyl)-1H-pyrrole-2,5-dione | 887144-79-8

• 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-decyl-1-(p-tolyl)-1H-pyrrole-2,5-dione
• 英文别名: 3-decyl-1-p-tolyl-pyrrole-2,5-dione；3-Decyl-1-(4-methylphenyl)pyrrole-2,5-dione
• CAS: 887144-79-8
• 化学式: C₂₁H₂₉NO₂
• 分子量: 327.467
• InChiKey: ZSNZYTFHZWYQFB-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60 °C(Solv: ligroine (8032-32-4); ethyl acetate (141-78-6))
• 沸点：
  457.4±24.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 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-decyl-1-(p-tolyl)-1H-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-bis-decyl-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：

  N-(4-Methylphenyl)-3-bromomaleimide 在 喹啉 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 6.0h， 生成 3-decyl-1-(p-tolyl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Sonogashira Coupling Reactions of Bromomaleimides: Route to Alkyne/cis-Alkene/Alkyl Maleimides: Synthesis of Luffarin X and Cacospongionolide C

  摘要：

  Palladium-catalyzed Sonogashira coupling reaction of bromomaleimides with a diverse range of terminal alkynes has been demonstrated to furnish the corresponding alkynylmaleimides in very good yields. This coupling reaction followed by selective reduction of the triple bond to single bond have been utilized as the decisive steps to accomplish the first total synthesis of natural products (+/-)-luffarin X and (+/-)-cacospongionolide C.

  DOI：

  10.1021/jo2021218