3-(4-chlorophenyl)-4,6-dimethoxyindole-2,7-dicarbaldehyde | 870193-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(4-chlorophenyl)-4,6-dimethoxyindole-2,7-dicarbaldehyde
• 英文别名: 3-(4-chlorophenyl)-4,6-dimethoxy-1H-indole-2,7-dicarbaldehyde
• CAS: 870193-27-4
• 化学式: C₁₈H₁₄ClNO₄
• 分子量: 343.766
• InChiKey: BHQQBKWXSMMULF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-4,6-dimethoxyindole-2,7-dicarbaldehyde 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以95%的产率得到3-(4-chlorophenyl)-2,7-dihydroxymethyl-4,6-dimethoxyindole
  参考文献：
  名称：

  Synthesis and utilisation of 2,7′-diindolylmethanes and a 2-(2-indolyl)pyrrolylmethane as macrocyclic precursors

  摘要：

  Treatment of 3-(4-chlorophenyl)-7-hydroxymethyl-4,6-dimethoxyindole with 3-(4-chlorophenyl)-4,6-dimethoxyindole results in the generation of two geometrically isomeric diindolylmethanes in addition to a novel triindolyl oligomer, which has been structurally characterised. The 2,7'-diindolylmethanes were found to be unstable under Vilsmeier formylation conditions, thus hampering macrocyle precursor construction. In an alternate approach, the 3-(4-chlorophenyl)-4,6-dimethoxyindole-7-carbaidehyde was converted into the indolyl-pyrrolyl macrocycle precursor 5-(3-(4-chlorophenyl)-4,6-dimethoxyindole-2-ylmethyl)-4-ethyl-3-methylpyrrole-2,7-dicarbaldehyde, which was used to generate an unsymmetrical pentaaza macrocycle. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.075
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 3-(4-chlorophenyl)-4,6-dimethoxyindole 在 三氯氧磷 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以70%的产率得到3-(4-chlorophenyl)-4,6-dimethoxyindole-2,7-dicarbaldehyde
  参考文献：
  名称：

  Synthesis and utilisation of 2,7′-diindolylmethanes and a 2-(2-indolyl)pyrrolylmethane as macrocyclic precursors

  摘要：

  Treatment of 3-(4-chlorophenyl)-7-hydroxymethyl-4,6-dimethoxyindole with 3-(4-chlorophenyl)-4,6-dimethoxyindole results in the generation of two geometrically isomeric diindolylmethanes in addition to a novel triindolyl oligomer, which has been structurally characterised. The 2,7'-diindolylmethanes were found to be unstable under Vilsmeier formylation conditions, thus hampering macrocyle precursor construction. In an alternate approach, the 3-(4-chlorophenyl)-4,6-dimethoxyindole-7-carbaidehyde was converted into the indolyl-pyrrolyl macrocycle precursor 5-(3-(4-chlorophenyl)-4,6-dimethoxyindole-2-ylmethyl)-4-ethyl-3-methylpyrrole-2,7-dicarbaldehyde, which was used to generate an unsymmetrical pentaaza macrocycle. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.075

文献信息

• Synthesis of Imine and Amine-Linked Macrocycles Containing Tris-Indoles
  作者：Hakan Kandemir、Ibrahim F. Sengul、Naresh Kumar、David StC. Black

  DOI：10.1071/ch17264

  日期：——

  7-nitroethylindoles is described. The 7-nitroethylindoles are converted to 2,2′-diindolylmethanes and the nitro groups reduced to amino. The resulting diamines undergo reactions with indole-2,7-dicarbaldehydes to form the macrocyclic imines, which can subsequently be reduced to the macrocyclic amines.

  描述了从7-硝基乙基吲哚开始的21元亚胺和胺连接的三吲哚大环的合成。7-硝基乙基吲哚被转化为2,2'-二吲哚基甲烷，硝基被还原为氨基。所得的二胺与吲哚-2，7-二甲醛反应形成大环亚胺，随后可将其还原为大环胺。
• A new synthetic route to pyrroloquinolines and pyrroloindoles
  作者：Karin Pchalek、Glenn C. Condie、Naresh Kumar、David StC. Black

  DOI：10.24820/ark.5550190.p011.405

  日期：——
• Synthesis and utilisation of 2,7′-diindolylmethanes and a 2-(2-indolyl)pyrrolylmethane as macrocyclic precursors
  作者：Paul K. Bowyer、David StC. Black、Donald C. Craig

  DOI：10.1016/j.tet.2005.08.075

  日期：2005.11

  Treatment of 3-(4-chlorophenyl)-7-hydroxymethyl-4,6-dimethoxyindole with 3-(4-chlorophenyl)-4,6-dimethoxyindole results in the generation of two geometrically isomeric diindolylmethanes in addition to a novel triindolyl oligomer, which has been structurally characterised. The 2,7'-diindolylmethanes were found to be unstable under Vilsmeier formylation conditions, thus hampering macrocyle precursor construction. In an alternate approach, the 3-(4-chlorophenyl)-4,6-dimethoxyindole-7-carbaidehyde was converted into the indolyl-pyrrolyl macrocycle precursor 5-(3-(4-chlorophenyl)-4,6-dimethoxyindole-2-ylmethyl)-4-ethyl-3-methylpyrrole-2,7-dicarbaldehyde, which was used to generate an unsymmetrical pentaaza macrocycle. (c) 2005 Elsevier Ltd. All rights reserved.