ethyl (3S)-5-bromo-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate | 1596355-35-9

• 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)-5-bromo-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate
• 英文别名: ethyl (3S)-5-bromo-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxoindole-3-carboxylate
• CAS: 1596355-35-9
• 化学式: C₂₂H₁₉BrN₂O₅
• 分子量: 471.307
• InChiKey: JWJRDCIAMSORQD-OPAMFIHVSA-N

物化性质

• 沸点：
  716.4±60.0 °C(predicted)
• 密度：
  1.543±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-溴-1-甲基-2-氧吲哚烷 在 sodium ethanolate 、 辛可尼丁 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 63.0h， 生成 ethyl (3S)-5-bromo-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate 、 ethyl (3R)-5-bromo-3-[(3R)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate 、 ethyl 5-bromo-3-[2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-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