3-(4-chlorophenyl)-4,6-dimethoxyindole-7-carbaldehyde | 362590-16-7

• 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-7-carbaldehyde
• 英文别名: 3-(4-chlorophenyl)-4,6-dimethoxy-1H-indole-7-carbaldehyde
• CAS: 362590-16-7
• 化学式: C₁₇H₁₄ClNO₃
• 分子量: 315.756
• InChiKey: YPORQTNFCOGSTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-(4-chlorophenyl)-4,6-dimethoxyindole-7-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以98%的产率得到3-(4-chlorophenyl)-7-hydroxymethyl-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， 反应 5.0h， 以84%的产率得到3-(4-chlorophenyl)-4,6-dimethoxyindole-7-carbaldehyde
  参考文献：
  名称：

  Indole-based mono- and poly-nuclear acyclic chelating systems: syntheses and selected transition metal complexes

  摘要：

  在二甲基甲酰胺中用磷酰氯处理 3-(4-氯苯基)-4,6-二甲氧基吲哚，生成区域选择性产物 3-(4-氯苯基)-4,6-二甲氧基吲哚-7-甲醛。它作为一种有价值的配体前体，与选定的二胺和三胺反应，产生许多新的无环配体。在乙腈中的三乙胺存在下，用选定的二价过渡金属乙酸盐处理这些配体，得到一系列具有不同核性的中性配合物，包括四面体和方形平面金属几何形状。除了报道的配体和配合物的化学和物理性质外，单晶分析还用于两种配体衍生物的几何分析：第一个是单核扭曲四面体外消旋镍（II）配合物；第二个是单核扭曲四面体外消旋镍（II）配合物。第二个是二镍异手性配合物。

  DOI：

  10.1039/b101350p

文献信息

• Small molecule inhibitors of bacterial transcription complex formation
  作者：Daniel S. Wenholz、Ming Zeng、Cong Ma、Marcin Mielczarek、Xiao Yang、Mohan Bhadbhade、David St. C. Black、Peter J. Lewis、Renate Griffith、Naresh Kumar

  DOI：10.1016/j.bmcl.2017.08.036

  日期：2017.9

  polymerase-σ70/σA interaction in bacteria. Synthesis was achieved via reactions between a variety of indole-7-carbaldehydes and rhodanine, N-allylrhodanine, barbituric acid or thiobarbituric acid. A library of structurally diverse compounds was examined by enzyme-linked immunosorbent assay (ELISA) to assess the inhibition of the targeted protein–protein interaction. Inhibition of bacterial growth was also evaluated

  Knoevenagel缩合物用于产生一组分子潜在地能够抑制RNA聚合酶的σ 70 / σ甲细菌相互作用。通过多种吲哚-7-甲醛与若丹宁，N-烯丙基罗丹宁，巴比妥酸或硫代巴比妥酸之间的反应实现合成。通过酶联免疫吸附测定（ELISA）检查了结构多样的化合物库，以评估对靶标蛋白质与蛋白质相互作用的抑制作用。还使用枯草芽孢杆菌和大肠杆菌评估了细菌生长的抑制作用文化。证明的用于RNA合成的分子的特定结构特征的重要性的结构-活性关系研究聚合酶σ 70 / σ甲相互作用抑制和抗菌活性。扩展坞是作为计算机方法进一步研究该化合物的计算机方法。
• Synthesis of novel 1,7-annulated 4,6-dimethoxyindoles
  作者：Kasey Wood、David StC Black、Irishi N.N. Namboothiri、Naresh Kumar

  DOI：10.1016/j.tetlet.2010.01.076

  日期：2010.3

  A range of new 1,7-annulated indole derivatives has been prepared via a ring-closing metathesis approach starting from N-allyl-7-formyl indoles. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of 7,7′-Linked-bis-Indoles via 7-Tryptamines
  作者：David StC. Black、Hakan Kandemir、Ibrahim F. Sengul、Christopher R. Gardner、Eryn L. Werry、Melissa L. Barron、Michael Kassiou

  DOI：10.3987/com-15-s(t)55

  日期：——

  The synthesis of 7-tryptamines was accomplished via the reduction of 7-nitrovinylindoles which were developed by the condensation of indole-7-carbaldehydes with nitromethane and ammonium acetate. 7-Tryptamines were subsequently used for the construction of 2,3-disubstituted and 3 -substituted 7,7'-linked-bis-indoles.
• Ring closing metathesis strategies towards functionalised 1,7-annulated 4,6-dimethoxyindoles
  作者：Kasey Wood、David StC Black、Naresh Kumar

  DOI：10.1016/j.tet.2011.04.019

  日期：2011.6

  A ring closing metathesis approach has been used to prepare a novel range of indoles 1,7-annulated with nitromethyl and lactone functionalised medium-sized rings. Initial studies into the preparation of lactam functionalised rings are also discussed. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of 5-(7′-indolyl)oxazoles and 2,5-di-(7′-indolyl)oxazoles
  作者：Hakan Kandemir、Kasey Wood、Naresh Kumar、David StC. Black

  DOI：10.1016/j.tet.2012.12.084

  日期：2013.3

  The synthesis of 7-aminoacetylindoles was achieved via the hydrogenation of 7-acylcyanides, which were produced through the oxidation of indole-7-cyanohydrin silylether intermediates. 7-Oxotryptamines were subsequently converted into 5-(7'-indolyl)oxazoles by reaction with acetic anhydride followed by phosphoryl chloride, and to 2,5-di-(7'-indolyl)oxazoles by reaction with 7-trichloroacetylindoles followed by phosphoryl chloride. (c) 2013 Elsevier Ltd. All rights reserved.