6-Methoxy-3-methyl-4,7-indoloquinone | 137542-69-9

• 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: 6-Methoxy-3-methyl-4,7-indoloquinone
• 英文别名: 6-methoxy-3-methylindole-4,7-dione；6-methoxy-3-methyl-1H-indole-4,7-dione
• CAS: 137542-69-9
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: YYEPRYXQNQAUNE-UHFFFAOYSA-N

物化性质

• 熔点：
  180-182 °C(Solv: ethanol (64-17-5))
• 沸点：
  431.5±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-methyl-4,6-dimethoxyindole-7-carbaldehyde 在 盐酸 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以47%的产率得到6-Methoxy-3-methyl-4,7-indoloquinone
  参考文献：
  名称：

  Synthesis of 4,7-indoloquinones from indole-7-carbaldehydes by Dakin oxidation

  摘要：

  Dakin oxidation of 4,6-dimethoxyindole-7-carbaldehydes, using hydrogen peroxide and hydrochloric acid, results in the synthesis of 6-methoxy-4,7-indoloquinones. The starting materials are readily available through the activation of the indole C7 position by the presence of the methoxy groups. Structural variation is possible through functionalities at C2 and C3. A 2,2'-di-indolylmethane-7,7'-dicarbaldehyde can also be oxidized to a bisindoloquinone under these conditions. The related oxidation of indole-7-carbaldehydes with m-chloroperbenzoic acid or preferably magnesium monoperphthalate instead leads to oxidation at C2 to give indol-2-ones. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.107

文献信息

• A novel entry to 4,7-indoloquinones via the Fremy's salt oxidative degradation of 4-formyl-7-hydroxyindoles
  作者：Jose M. Saa、Catalina Marti、Angel Garcia-Raso

  DOI：10.1021/jo00028a035

  日期：1992.1

  A novel synthetic approach toward 4-formyl-7-hydroxyindoles and 4,7-indoloquinones is described. Basically, two major operations need to be carried out, namely: (1) ozonization of the appropriately protected 4-amino-5-hydroxyindenes leading eventually to 4-formyl-7-hydroxyindoles and (2) Fremy's salt promoted oxidative degradation of the later compounds to the desired 4,7-indoloquinones. A formal synthesis of PDE I and PDE II has been achieved.