3-(2-phenyl-2-hydroxyethyl)-4,6-dibromoindole

• 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-phenyl-2-hydroxyethyl)-4,6-dibromoindole
• 英文别名: 2-(4,6-dibromo-1H-indol-3-yl)-1-phenylethanol
• 化学式: C₁₆H₁₃Br₂NO
• 分子量: 395.093
• InChiKey: JKFCKLPQMRPDAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4,6-二溴靛红 在 硼烷四氢呋喃络合物 、 二乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 3-(2-phenyl-2-hydroxyethyl)-4,6-dibromoindole
  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

文献信息

• A versatile synthetic methodology for the synthesis of tryptophols
  作者：Simon J Garden、Rosângela B da Silva、Angelo C Pinto

  DOI：10.1016/s0040-4020(02)01048-7

  日期：2002.10

  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.