3-Acetyloxindol | 99224-31-4

• 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: 3-Acetyloxindol
• 英文别名: 1-(2-hydroxy-1H-indol-3-yl)ethanone
• CAS: 99224-31-4
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: GCHBFPDGJVIFQY-UHFFFAOYSA-N

物化性质

• 熔点：
  195-197 °C
• 沸点：
  368.9±22.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Acetyloxindol 、 methyl 4-phenyl-2-oxo-3-butenoate 生成
  参考文献：
  名称：

  Organocatalytic asymmetric cascade Michael/hemiketalization/retro-aldol reaction of 3-acetyl-oxindole with β,γ-unsaturated ketoesters catalyzed by bifunctional amino-squaramides

  摘要：

  An unprecedented organocatalytic asymmetric Michael/Hemiketalization/retro-aldol cascade sequence catalyzed by bifunctional amino-squaramides is described. The corresponding adducts were generally obtained in high yields (up to 97%) with moderate diastereo- (up to 79:21 dr) and good enantioselectivities (up to 90% ee). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.040
• 作为产物：
  描述：

  N-乙酰基-2-羟基吲哚 在 4-二甲氨基吡啶 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 3-Acetyloxindol
  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

• SETSUNE, JUN-ICHIRO;MATSUKAWA, KIMIHIRO;KITAO, TEIJIRO, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM., 1985, N 3, 438-441
  作者：SETSUNE, JUN-ICHIRO、MATSUKAWA, KIMIHIRO、KITAO, TEIJIRO

  DOI：——

  日期：——