(3-((2-amino-4-fluorophenyl)amino)-1-benzyl-2-oxoindolin-3-yl)methyl tert-butyl carbonate | 1598427-85-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3-((2-amino-4-fluorophenyl)amino)-1-benzyl-2-oxoindolin-3-yl)methyl tert-butyl carbonate
• CAS: 1598427-85-0
• 化学式: C₂₇H₂₈FN₃O₄
• 分子量: 477.535
• InChiKey: DMCZNVFBAWKGLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  93.89
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3-((2-amino-4-fluorophenyl)amino)-1-benzyl-2-oxoindolin-3-yl)methyl tert-butyl carbonate 、 原甲酸三乙酯 在 对甲苯磺酸 作用下， 反应 8.0h， 以96%的产率得到(1-benzyl-3-(5-fluoro-1H-benzo[d]imidazol-1-yl)-2-oxoindolin-3-yl)methyl tert-butyl carbonate
  参考文献：
  名称：

  Synthesis of 3-Amino-3-hydroxymethyloxindoles and 3-Hydroxy-3-hydroxymethyloxindoles by Rh₂(OAc)₄-Catalyzed Three-Component Reactions of 3-Diazooxindoles with Formaldehyde and Anilines or Water

  摘要：

  Efficient Rh(II)-catalyzed three-component reactions of 3-diazooxindoles and formaldehyde with either anilines or water were developed to give a series of substituted 3-amino-3-hydroxymethyloxindoles or 3-hydroxy-3-hydroxymethyloxindoles in good to excellent yields. In this atom- and step-economic transformation, Rh-2(OAc)(4)-catalyzed decomposition of 3-diazooxindoles with anilines or water forms the corresponding active ammonium or oxonium ylides. Electrophilic trapping of the resulting ammonium ylides or oxonium ylides by formaldehyde in the form of formalin efficiently produces the title compounds in one step.

  DOI：

  10.1021/jo500307n
• 作为产物：
  描述：

  1-benzyl-3-diazo-1,3-dihydro-2H-indol-2-one 在 4-二甲氨基吡啶 、 dirhodium tetraacetate 、 5%-palladium/activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 18.0h， 生成 (3-((2-amino-4-fluorophenyl)amino)-1-benzyl-2-oxoindolin-3-yl)methyl tert-butyl carbonate
  参考文献：
  名称：

  Synthesis of 3-Amino-3-hydroxymethyloxindoles and 3-Hydroxy-3-hydroxymethyloxindoles by Rh₂(OAc)₄-Catalyzed Three-Component Reactions of 3-Diazooxindoles with Formaldehyde and Anilines or Water

  摘要：

  Efficient Rh(II)-catalyzed three-component reactions of 3-diazooxindoles and formaldehyde with either anilines or water were developed to give a series of substituted 3-amino-3-hydroxymethyloxindoles or 3-hydroxy-3-hydroxymethyloxindoles in good to excellent yields. In this atom- and step-economic transformation, Rh-2(OAc)(4)-catalyzed decomposition of 3-diazooxindoles with anilines or water forms the corresponding active ammonium or oxonium ylides. Electrophilic trapping of the resulting ammonium ylides or oxonium ylides by formaldehyde in the form of formalin efficiently produces the title compounds in one step.

  DOI：

  10.1021/jo500307n