diethyl (Z)-2-(1-methyl-2-oxo-3H-indol-4-yl)but-2-enedioate | 1196150-97-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: diethyl (Z)-2-(1-methyl-2-oxo-3H-indol-4-yl)but-2-enedioate
• CAS: 1196150-97-6
• 化学式: C₁₇H₁₉NO₅
• 分子量: 317.342
• InChiKey: AAVPXVNNLJSARW-RAXLEYEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-溴-1,3-二氢-1-甲基-2H-吲哚-2-酮 、 富马酸二乙酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 16.0h， 生成 、 diethyl (Z)-2-(1-methyl-2-oxo-3H-indol-4-yl)but-2-enedioate
  参考文献：
  名称：

  Synthesis of the Bicyclic Welwitindolinone Core via an Alkylation/Cyclization Cascade Reaction

  摘要：

  Synthesis of an advanced welwitindolinone intermediate via an alkylation/cyclization reaction Is reported. The key step involves a one pot Lewis acid-mediated alkylation of a silylketene aminal with a furan alcohol followed by an intramolecular cyclization. The reaction is stereoselective and takes place at low temperature. The cycloadduct was highly functionalized and contains the welwitindolinone core structure.

  DOI：

  10.1021/ol902173g

文献信息

• Synthesis of the Bicyclic Welwitindolinone Core via an Alkylation/Cyclization Cascade Reaction
  作者：John A. Brailsford、Ryan Lauchli、Kenneth J. Shea

  DOI：10.1021/ol902173g

  日期：2009.11.19

  Synthesis of an advanced welwitindolinone intermediate via an alkylation/cyclization reaction Is reported. The key step involves a one pot Lewis acid-mediated alkylation of a silylketene aminal with a furan alcohol followed by an intramolecular cyclization. The reaction is stereoselective and takes place at low temperature. The cycloadduct was highly functionalized and contains the welwitindolinone core structure.