3-(2-hydroxypropyl)-3-hydroxy-2-oxindole | 500219-94-3

• 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: 3-(2-hydroxypropyl)-3-hydroxy-2-oxindole
• 英文别名: 3-hydroxy-3-(2-hydroxypropyl)-1H-indol-2-one
• CAS: 500219-94-3
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: VHVQUCYGLSMVNS-UHFFFAOYSA-N

物化性质

• 熔点：
  194-195 °C
• 沸点：
  453.1±45.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-hydroxypropyl)-3-hydroxy-2-oxindole 在 硼烷四氢呋喃络合物 作用下， 以100%的产率得到3-<2-Hydroxy-propyl>-indol
  参考文献：
  名称：

  A versatile synthetic methodology for the synthesis of tryptophols

  摘要：

  Tryptophols have been obtained in high yields by the reduction of 3-substituted-dioxindoles (obtained by the aldol condensation reaction of ketones with isatins or by a modified Knovenagel malonate condensation) using a borane tetrahydrofuran complex. The reported methodology offers distinct advantages over existing methods for the synthesis of these compounds, including consistently greater yields, diastereoselective syntheses and the possibility for the synthesis of a wide range of structurally different tryptophols. The reduction reaction was found to proceed via an intermediate 1,3-diol-oxindole, which was obtained diastereoselectively and, which was subsequently reduced to the corresponding tryptophol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01048-7
• 作为产物：
  描述：

  1,3-二氢-3-羟基-3-(2-氧代丙基)-2H-吲哚-2-酮 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以21%的产率得到3-(2-hydroxypropyl)-3-hydroxy-2-oxindole
  参考文献：
  名称：

  A versatile synthetic methodology for the synthesis of tryptophols

  摘要：

  Tryptophols have been obtained in high yields by the reduction of 3-substituted-dioxindoles (obtained by the aldol condensation reaction of ketones with isatins or by a modified Knovenagel malonate condensation) using a borane tetrahydrofuran complex. The reported methodology offers distinct advantages over existing methods for the synthesis of these compounds, including consistently greater yields, diastereoselective syntheses and the possibility for the synthesis of a wide range of structurally different tryptophols. The reduction reaction was found to proceed via an intermediate 1,3-diol-oxindole, which was obtained diastereoselectively and, which was subsequently reduced to the corresponding tryptophol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01048-7