1,3-diacetyl-5-nitro-1H-indol-2-yl acetate | 1214260-91-9

• 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: 1,3-diacetyl-5-nitro-1H-indol-2-yl acetate
• CAS: 1214260-91-9
• 化学式: C₁₄H₁₂N₂O₆
• 分子量: 304.259
• InChiKey: CMILZPCUYVYBHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  108.51
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,3-diacetyl-5-nitro-1H-indol-2-yl acetate 在 immobilized Candida antarctica Lipase B 、 正丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以100%的产率得到1,3-diacetyl-5-nitro-2-hydroxylndole
  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
• 作为产物：
  描述：

  5-硝基-1,3-二氢-2H-吲哚-2-酮 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 反应 4.0h， 以76%的产率得到1,3-diacetyl-5-nitro-1H-indol-2-yl acetate
  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