(S)-1-acetyl-2-((S)-1-(furan-2-yl)-2-nitroethyl)indolin-3-one | 1276688-11-9

• 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: (S)-1-acetyl-2-((S)-1-(furan-2-yl)-2-nitroethyl)indolin-3-one
• 英文别名: (2S)-1-acetyl-2-[(1S)-1-(furan-2-yl)-2-nitroethyl]-2H-indol-3-one
• CAS: 1276688-11-9
• 化学式: C₁₆H₁₄N₂O₅
• 分子量: 314.298
• InChiKey: GCUXQUDRFMUSHY-DOMZBBRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  96.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(2-糠酰)-2-硝基乙烯 、 N-乙酰基-3-吲哚啉酮 在 N-[3,5-双(三氟甲基)苯基]-N'-[(8a,9S)-6'-甲氧基-9-金鸡宁]硫脲 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 1-acetyl-2-(1-(furan-2-yl)-2-nitroethyl)indolin-3-one 、 (S)-1-acetyl-2-((S)-1-(furan-2-yl)-2-nitroethyl)indolin-3-one 、 (R)-1-acetyl-2-((R)-1-(furan-2-yl)-2-nitroethyl)indolin-3-one
  参考文献：
  名称：

  Asymmetric Michael Addition of 1-Acetylindolin-3-ones to β-Nitrostyrenes Catalyzed by Bifunctional Thioureas: A Simple Access to 2-Functionalized Indoles

  摘要：

  The first asymmetric Michael addition of 1-acetylindolin-3-ones to beta-nitrostyrenes has been developed. 2-Substituted indolin-3-one derivatives were obtained with excellent yields (up to 99%) and good stereoselectivities (up to 28:1 dr and 92% ee), which could be transformed into 2-functionalized indoles easily without racemization. This achievement might further contribute to the chemistry and pharmacology of indole-related compounds.

  DOI：

  10.1021/jo102022g

文献信息

• Asymmetric Michael Addition of 1-Acetylindolin-3-ones to β-Nitrostyrenes Catalyzed by Bifunctional Thioureas: A Simple Access to 2-Functionalized Indoles
  作者：Yao-Zong Liu、Rui-Ling Cheng、Peng-Fei Xu

  DOI：10.1021/jo102022g

  日期：2011.4.15

  The first asymmetric Michael addition of 1-acetylindolin-3-ones to beta-nitrostyrenes has been developed. 2-Substituted indolin-3-one derivatives were obtained with excellent yields (up to 99%) and good stereoselectivities (up to 28:1 dr and 92% ee), which could be transformed into 2-functionalized indoles easily without racemization. This achievement might further contribute to the chemistry and pharmacology of indole-related compounds.