(E)-3-(3-(tert-butyldimethylsilyloxy)-1-(trimethylsilyl)propylidene)-2-(1H-pyrrol-1-yl)isoindolin-1-one | 1453503-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (E)-3-(3-(tert-butyldimethylsilyloxy)-1-(trimethylsilyl)propylidene)-2-(1H-pyrrol-1-yl)isoindolin-1-one
• 英文别名: (3E)-3-[3-[tert-butyl(dimethyl)silyl]oxy-1-trimethylsilylpropylidene]-2-pyrrol-1-ylisoindol-1-one
• CAS: 1453503-84-8
• 化学式: C₂₄H₃₆N₂O₂Si₂
• 分子量: 440.733
• InChiKey: KKVUNZSHGQNNMQ-QURGRASLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyldimethyl(4-(trimethylsilyl)but-3-ynyloxy)silane 、 2-(1H-吡咯-1-基)异吲哚啉-1,3-二酮 在 bis(1,5-cyclooctadiene)nickel (0) 、 甲铝双(2,6-二叔丁基-4-苯甲醚) 、 三甲基膦 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以90%的产率得到(E)-3-(3-(tert-butyldimethylsilyloxy)-1-(trimethylsilyl)propylidene)-2-(1H-pyrrol-1-yl)isoindolin-1-one
  参考文献：
  名称：

  Nickel-Catalyzed Decarbonylative Alkylidenation of Phthalimides with Trimethylsilyl-Substituted Alkynes

  摘要：

  We have developed a nickel-catalyzed transformation, in which phthalimides react with trimethylsilyl-substituted alkynes in the presence of Ni(0)/PMe3/MAD catalyst to provide isoindolinones. The reaction process displays an unusual mechanistic feature-decarbonylation and alkylidenation. The use of both trimethylsilyl-substiuted alkynes and MAD was found to be essential for the transformation with high selectivities.

  DOI：

  10.1021/ja4068172

文献信息

• Nickel-Catalyzed Decarbonylative Alkylidenation of Phthalimides with Trimethylsilyl-Substituted Alkynes
  作者：Takahiro Shiba、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1021/ja4068172

  日期：2013.9.18

  We have developed a nickel-catalyzed transformation, in which phthalimides react with trimethylsilyl-substituted alkynes in the presence of Ni(0)/PMe3/MAD catalyst to provide isoindolinones. The reaction process displays an unusual mechanistic feature-decarbonylation and alkylidenation. The use of both trimethylsilyl-substiuted alkynes and MAD was found to be essential for the transformation with high selectivities.