3-methyl-4,6-dimethoxyindole-7-carbaldehyde | 100997-51-1

• 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-methyl-4,6-dimethoxyindole-7-carbaldehyde
• 英文别名: 4,6-dimethoxy-3-methyl-1H-indole-7-carbaldehyde
• CAS: 100997-51-1
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: HLUPCBMZHFBEPE-UHFFFAOYSA-N

物化性质

• 熔点：
  185-186 °C
• 沸点：
  443.2±40.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  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
• 作为产物：
  描述：

  4,6-二甲氧基-3-甲基吲哚 、 N,N-二甲基甲酰胺 以46%的产率得到
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• 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。
• A Ready Synthesis of 4-Oxo-4<i>H</i>-pyrrolo[3,2,1-<i>ij</i>]quinolines
  作者：David St. C. Black、Andrew J. Ivory、Paul A. Keller、Naresh Kumar

  DOI：10.1055/s-1989-27243

  日期：——

  4,6-Dimethoxy-7-formylindoles undergo condensation with ethyl acetate in the presence of sodium ethoxide to yield new 4-oxo-4H-pyrrolo[3,2,1-ij]quinolines.

  4,6-二甲氧基-7-甲酰基吲哚在乙醇钠存在下与乙酸乙酯缩合，生成新的4-氧代-4H-吡咯并[3,2,1-ij]喹啉。
• Nickel(II) complexes of imine ligands derived from 7-formylindoles
  作者：David St C. Black、Donald C. Craig、Naresh Kumar、Laurence C. H. Wong

  DOI：10.1039/c39850001172

  日期：——

  Quadridentate bis-imine nickel(II) complexes have been formed from 7-formylindoles and 1,2-diamnobenzene: an X-ray crystal structure determination of the chloroform solvate of the N,N′-bis(4,6-dimethoxyindol-7-ylidene)-1,2-diaminobenzene complex shows severe distortion from planarity and a distance of 2.96 Å between the C-2 indole atoms.

  由7-甲酰基吲哚和1,2-二苯胺形成四重双亚胺镍（II）络合物：X射线晶体结构测定N，N'-双（4,6-二甲氧基吲哚-7）的氯仿溶剂化物-亚烷基）-1,2-二氨基苯配合物显示出严重的平面度变形，并且C-2吲哚原子之间的距离为2.96Å。
• Synthesis of Some (Triindolyl)dimethanes and (Tetraindolyl)trimethanes
  作者：David StC. Black、Kittya Somphol、Naresh Kumar

  DOI：10.3987/com-20-14397

  日期：——
• Synthesis of Semi-Calix[4]indoles Containing Combinations of Direct Links and Methylene Linkages
  作者：David Black、Rui Chen、Kittiya Somphol、Mohan Bhadbhade、Naresh Kumar

  DOI：10.1055/s-0033-1338868

  日期：——

  Macrocyclic compounds containing four 3-substituted-4,6-dimethoxyindole units joined through the C2 and C7 positions, by a combination of direct links or methylene bridges, can be prepared by acid-catalyzed reactions of indole methanols and 2,7'-biindolyldimethanols with indoles and 2,7'-biindolyls.