5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole-8-carbaldehyde | 123846-58-2

• 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: 5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole-8-carbaldehyde
• 英文别名: 2,4-dimethoxy-6,7,8,9-tetrahydro-5H-carbazole-1-carbaldehyde
• CAS: 123846-58-2
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: LBGSVTAJEILSRC-UHFFFAOYSA-N

物化性质

• 沸点：
  486.3±40.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.32
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole-8-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50%的产率得到2-methoxy-5,6,7,8-tetrahydro-9H-carbazole-1,4-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：

  3,5-二甲氧基苯胺 在 sodium hydroxide 、 3,5-dimethoxyaniline hydrobromide 、 三氯氧磷 作用下， 以 various solvent(s) 为溶剂， 反应 4.5h， 生成 5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole-8-carbaldehyde
  参考文献：
  名称：

  Black, David St. C.; Keller, Paul A.; Kumar, Naresh, Australian Journal of Chemistry, 1993, vol. 46, # 6, p. 843 - 862

  摘要：

  DOI：

文献信息

• 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。
• BLACK, DAVID ST. C.;IVORY, ANDREW J.;KELLER, PAUL A.;KUMAR, NARESH, SYNTHESIS,(1989) N, C. 322-323
  作者：BLACK, DAVID ST. C.、IVORY, ANDREW J.、KELLER, PAUL A.、KUMAR, NARESH

  DOI：——

  日期：——
• Black David St. C., Keller Paul A., Kumar Naresh, Austral. J. Chem., 46 (1993) N 6, S 843-862
  作者：Black David St. C., Keller Paul A., Kumar Naresh

  DOI：——

  日期：——
• Black, David St. C.; Keller, Paul A.; Kumar, Naresh, Australian Journal of Chemistry, 1993, vol. 46, # 6, p. 843 - 862
  作者：Black, David St. C.、Keller, Paul A.、Kumar, Naresh

  DOI：——

  日期：——
• 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.