5-methoxy-1,3-dimethyl-3-(3,3,3-trifluoropropyl)indolin-2-one

• 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: 5-methoxy-1,3-dimethyl-3-(3,3,3-trifluoropropyl)indolin-2-one
• 英文别名: 5-Methoxy-1,3-dimethyl-3-(3,3,3-trifluoropropyl)indol-2-one；5-methoxy-1,3-dimethyl-3-(3,3,3-trifluoropropyl)indol-2-one
• 化学式: C₁₄H₁₆F₃NO₂
• 分子量: 287.282
• InChiKey: GJFUHSFLWAWBHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-碘-1,1,1-三氟乙烷 、 N-(4-methoxyphenyl)-N,2-dimethylacrylamide 在 rongalite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以58%的产率得到5-methoxy-1,3-dimethyl-3-(3,3,3-trifluoropropyl)indolin-2-one
  参考文献：
  名称：

  Metal-free trifluoroethylation of activated alkenes: rapid access to construct fluorinated 3,3-disubstituted 2-oxindoles

  摘要：

  A novel and mild fluorination/cyclization reaction of activated alkenes under metal-free conditions has been developed. Fluorinated radicals were produced from halogenated hydrocarbons by simple rongalit, meanwhile, no metal and extra base are needed. This method provides a general and rapid route to construct fluorinated 2-oxindoles in aqueous solution. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.004

文献信息

• Photoredox-Catalyzed Tandem Radical Cyclization of <i>N</i>-Arylacrylamides: General Methods To Construct Fluorinated 3,3-Disubstituted 2-Oxindoles Using Fluoroalkylsulfonyl Chlorides
  作者：Xiao-Jun Tang、Charles S. Thomoson、William R. Dolbier

  DOI：10.1021/ol502163f

  日期：2014.9.5

  Fluorinated radicals were generated from RfSO2Cl by photoredox catalysis under mild conditions, where Rf = n-C4F9, CF3, CF2H, CH2F, CH2CF3, and CF2CO2Me. This method provided a general way to construct fluorinated 2-oxindoles from reaction with N-arylacrylamides via a proposed tandem radical cyclization process.
• Metal-free trifluoroethylation of activated alkenes: rapid access to construct fluorinated 3,3-disubstituted 2-oxindoles
  作者：Wen-Peng Mai、Bin Sun、Guan-Sheng Qian、Jin-Wei Yuan、Pu Mao、Liang-Ru Yang、Yong-Mei Xiao

  DOI：10.1016/j.tet.2015.09.004

  日期：2015.11

  A novel and mild fluorination/cyclization reaction of activated alkenes under metal-free conditions has been developed. Fluorinated radicals were produced from halogenated hydrocarbons by simple rongalit, meanwhile, no metal and extra base are needed. This method provides a general and rapid route to construct fluorinated 2-oxindoles in aqueous solution. (C) 2015 Elsevier Ltd. All rights reserved.