1,3-diacetyl-1H-indol-2-yl acetate | 1195737-72-4

• 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-1H-indol-2-yl acetate
• 英文别名: (1,3-Diacetylindol-2-yl) acetate；(1,3-diacetylindol-2-yl) acetate
• CAS: 1195737-72-4
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: JEXPVJXBZRMWNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  65.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-diacetyl-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 1.0h， 以100%的产率得到1,3-diacetyl-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：

  靛红 在 4-二甲氨基吡啶 、 一水合肼 、 potassium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 5.0h， 生成 1,3-diacetyl-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

文献信息

• Highly efficient one-pot C-, N- and O-acylation of indolin-2-one analogs
  作者：Mukund Jha、Brian Blunt

  DOI：10.1016/j.tetlet.2009.08.057

  日期：2009.11

  A highly efficient one-pot multiple acylation at chemically non-equivalent sites on indolin-2-one and related motifs using 4-(N,N-dimethylamino)pyridine as a catalyst is described. This procedure gives extremely facile entry to highly desired 3-acyl-2-hydroxy-indole synthons among other derivatives. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.