ethyl (3S)-1-methyl-3-[(3S)-1-(3-nitrophenyl)-2,5-dioxopyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate | 1596355-28-0

• 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)-1-methyl-3-[(3S)-1-(3-nitrophenyl)-2,5-dioxopyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate
• 英文别名: ethyl (3S)-1-methyl-3-[(3S)-1-(3-nitrophenyl)-2,5-dioxopyrrolidin-3-yl]-2-oxoindole-3-carboxylate
• CAS: 1596355-28-0
• 化学式: C₂₂H₁₉N₃O₇
• 分子量: 437.409
• InChiKey: ICJRFCLNAVGSGH-OPAMFIHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  32
• 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：
  130
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-甲基吲哚酮 在 sodium ethanolate 、 辛可尼丁 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 39.0h， 生成 ethyl (3S)-1-methyl-3-[(3S)-1-(3-nitrophenyl)-2,5-dioxopyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate 、 ethyl (3R)-1-methyl-3-[(3R)-1-(3-nitrophenyl)-2,5-dioxopyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate 、 ethyl 1-methyl-3-[1-(3-nitrophenyl)-2,5-dioxopyrrolidin-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

文献信息

• Efficient asymmetric Michael reaction of 2-oxindole-3-carboxylate esters with maleimides catalyzed by cinchonidine
  作者：Jing Zhou、Li-Na Jia、Lin Peng、Qi-Lin Wang、Fang Tian、Xiao-Ying Xu、Li-Xin Wang

  DOI：10.1016/j.tet.2014.03.065

  日期：2014.5

  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.