ethyl (3S)-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-2-oxo-1-(prop-2-en-1-yl)-2,3-dihydro-1H-indole-3-carboxylate | 1596355-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl (3S)-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-2-oxo-1-(prop-2-en-1-yl)-2,3-dihydro-1H-indole-3-carboxylate
• CAS: 1596355-39-3
• 化学式: C₂₄H₂₂N₂O₅
• 分子量: 418.449
• InChiKey: OEUXTYMYRCTKIS-HOYKHHGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1-allylindolin-2-one 在 sodium ethanolate 、 辛可尼丁 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 17.0h， 生成 ethyl (3S)-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-2-oxo-1-(prop-2-en-1-yl)-2,3-dihydro-1H-indole-3-carboxylate 、 ethyl (3R)-3-[(3R)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-2-oxo-1-(prop-2-en-1-yl)-2,3-dihydro-1H-indole-3-carboxylate 、 ethyl 3-[2,5-dioxo-1-phenylpyrrolidin-3-yl]-2-oxo-1-(prop-2-en-1-yl)-2,3-dihydro-1H-indole-3-carboxylate
  参考文献：
  名称：

  Efficient asymmetric Michael reaction of 2-oxindole-3-carboxylate esters with maleimides catalyzed by cinchonidine

  摘要：

  A highly efficient enantioselective Michael reaction of 2-oxindole-3-carboxylate esters with N-maleimides catalyzed by commercially available cinchonidine was described. The desired adducts, containing a quaternary center at the C3-position and a vicinal tertiary center, were obtained in excellent yields (up to 99%), good enantioselectivities (up to 85% ee), and diastereoselectivities (dr>90:10) in the presence of 0.05-5 mol % catalyst loading. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.065