3-acetyl-5-bromo-2-hydroxyindole | 1268630-40-5

• 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-acetyl-5-bromo-2-hydroxyindole
• CAS: 1268630-40-5
• 化学式: C₁₀H₈BrNO₂
• 分子量: 254.083
• InChiKey: ZAVKHVVTISWVKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  53.09
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  5-溴氧化吲哚 在 4-二甲氨基吡啶 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3-acetyl-5-bromo-2-hydroxyindole
  参考文献：
  名称：

  General synthesis of mono-, di-, and tri-acetylated indoles from indolin-2-ones

  摘要：

  Having developed the one-pot triacetylation of indolin-3-ones, we have now devised a simple two-step reaction sequences to produce di- and mono-acetylated indoles from indolin-2-ones. The indolin-2-ones were first subjected to acetylation in the presence of acetic anhydride and a catalytic amount of N,N-dimethylaminopyridine to give 2-acetoxy-1,3-diacetylindoles. Subsequently, an enzyme-assisted deacetylation resulted in the chemoselective deprotection of the acetoxy group to produce 1,3-diacetyl-2-hydroxyindoles. However, a chemical deacetylation of 2-acetoxy-1,3-diacetylinoles under mild basic or acidic conditions resulted in the formation of 3-acetyl-2-hydroxyindoles. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.105

文献信息

• General synthesis of mono-, di-, and tri-acetylated indoles from indolin-2-ones
  作者：Mukund Jha、Ting-Yi Chou、Brian Blunt

  DOI：10.1016/j.tet.2010.11.105

  日期：2011.2

  Having developed the one-pot triacetylation of indolin-3-ones, we have now devised a simple two-step reaction sequences to produce di- and mono-acetylated indoles from indolin-2-ones. The indolin-2-ones were first subjected to acetylation in the presence of acetic anhydride and a catalytic amount of N,N-dimethylaminopyridine to give 2-acetoxy-1,3-diacetylindoles. Subsequently, an enzyme-assisted deacetylation resulted in the chemoselective deprotection of the acetoxy group to produce 1,3-diacetyl-2-hydroxyindoles. However, a chemical deacetylation of 2-acetoxy-1,3-diacetylinoles under mild basic or acidic conditions resulted in the formation of 3-acetyl-2-hydroxyindoles. (C) 2010 Elsevier Ltd. All rights reserved.