11-(2,5-dioxo-1-(p-tolyl)-2,5-dihydro-1H-pyrrol-3-yl)undec-10-ynoic acid | 1353013-46-3

• 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: 11-(2,5-dioxo-1-(p-tolyl)-2,5-dihydro-1H-pyrrol-3-yl)undec-10-ynoic acid
• 英文别名: 11-[1-(4-Methylphenyl)-2,5-dioxopyrrol-3-yl]undec-10-ynoic acid
• CAS: 1353013-46-3
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: LGENPFAOJCDZNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(4-Methylphenyl)-3-bromomaleimide 、 10-十一碳炔酸 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以63%的产率得到11-(2,5-dioxo-1-(p-tolyl)-2,5-dihydro-1H-pyrrol-3-yl)undec-10-ynoic acid
  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

文献信息

• Sonogashira Coupling Reactions of Bromomaleimides: Route to Alkyne/<i>cis</i>-Alkene/Alkyl Maleimides: Synthesis of Luffarin X and Cacospongionolide C
  作者：Prashant S. Deore、Narshinha P. Argade

  DOI：10.1021/jo2021218

  日期：2012.1.6

  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.