2,3-dimethyl-4,6-dimethoxyindole-7-carbaldehyde | 107167-04-4

• 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: 2,3-dimethyl-4,6-dimethoxyindole-7-carbaldehyde
• 英文别名: 4,6-dimethoxy-2,3-dimethyl-1H-indole-7-carbaldehyde
• CAS: 107167-04-4
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: FJJLPYKEJGTKJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dimethyl-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31%的产率得到6-methoxy-2,3-dimethylindole-4,7-dione
  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
• 作为产物：
  描述：

  4,6-dimethoxy-2,3-dimethylindole 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 1.0h， 以64%的产率得到2,3-dimethyl-4,6-dimethoxyindole-7-carbaldehyde
  参考文献：
  名称：

  Synthesis of 2-(7-Indolyl)-benzimidazoles via 7-Formylindoles

  摘要：

  4,6-二甲氧基吲哚经过Vilsmeier甲酰化反应生成7-甲酰基吲哚，这些产物在与1,2-二氨基苯反应时可转化为2-(7-吲哚基)-苯并咪唑。

  DOI：

  10.1055/s-1986-31678

文献信息

• BLACK, D. ST. C.;KUMAR, NARESH;WONG, L. C. H., SYNTHESIS, BRD, 1986, N 6, 474-476
  作者：BLACK, D. ST. C.、KUMAR, NARESH、WONG, L. C. H.

  DOI：——

  日期：——
• Synthesis of 2-(7-Indolyl)-benzimidazoles via 7-Formylindoles
  作者：David St C. Black、Naresh Kumar、Laurence C. H. Wong

  DOI：10.1055/s-1986-31678

  日期：——

  4,6-Dimethoxyindoles undergo Vilsmeier formylation to give 7-formylindoles which can be converted into 2-(7-indolyl)-benzimidazoles on reaction with 1,2-diaminobenzene.

  4,6-二甲氧基吲哚经过Vilsmeier甲酰化反应生成7-甲酰基吲哚，这些产物在与1,2-二氨基苯反应时可转化为2-(7-吲哚基)-苯并咪唑。
• Synthesis of 4,7-indoloquinones from indole-7-carbaldehydes by Dakin oxidation
  作者：Mahiuddin Alamgir、Peter S.R. Mitchell、Paul K. Bowyer、Naresh Kumar、David StC. Black

  DOI：10.1016/j.tet.2008.05.107

  日期：2008.7

  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.