1-(4-chlorophenyl)-5-methoxy-1H-indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(4-chlorophenyl)-5-methoxy-1H-indole
• 英文别名: 1-(4-Chlorophenyl)-5-methoxyindole
• 化学式: C₁₅H₁₂ClNO
• 分子量: 257.719
• InChiKey: DILGVUZDYSVXEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-甲氧基吲哚 、 对氯碘苯 在 copper(l) iodide 、 盐酸二甲双胍 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以91%的产率得到1-(4-chlorophenyl)-5-methoxy-1H-indole
  参考文献：
  名称：

  Synthesis of 1-aryl indoles via coupling reaction of indoles and aryl halides catalyzed by CuI/metformin

  摘要：

  Ullmann-type C-N coupling reaction has been developed for the synthesis of 1-aryl indole derivatives by indoles and aryl halides in the presence of CuI/metformin (CuI/Met) in DMF. This method is very easy, rapid, and high yielding reaction for the synthesis of 1-aryl indoles. In particular, the metformin, which is used as ligand, is inexpensive and nontoxic that is considered to be relatively environmentally benign. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.080

文献信息

• Insights on Bimetallic Micellar Nanocatalysis for Buchwald–Hartwig Aminations
  作者：Tharique N. Ansari、Armand Taussat、Adam H. Clark、Maarten Nachtegaal、Scott Plummer、Fabrice Gallou、Sachin Handa

  DOI：10.1021/acscatal.9b02622

  日期：2019.11.1

  their linkage with the activated carbon surface is revealed by XAS analysis. Control NMR experiments revealed the binding of the ligand with both Cu and Pd, and all phosphine molecules are under the same environment. In addition to NMR and XAS analysis, the catalyst is characterized by SEM, HRTEM, XPS, and TGA. Reactions are highly reproducible at variable scales. Environmentally benign, proline-based

  胶束布赫瓦尔德-哈特维格胺胺化的纳米催化剂已经开发，充分表征并应用于多种底物上。该催化剂在环境条件下稳定至少六个月。催化剂在几个循环后仍保持其活性，并且如NMR光谱所证实的，其结构保持完整。31揭示了磷化氢配体使Pd纳米颗粒与Cu缔合通过XAS分析揭示了P NMR光谱及其与活性炭表面的联系。对照NMR实验表明，配体与Cu和Pd均结合，所有膦分子均处于同一环境中。除了NMR和XAS分析之外，该催化剂还通过SEM，HRTEM，XPS和TGA进行表征。反应在可变规模下可高度重现。环境友好的脯氨酸基两亲物PS-750-M对于催化活性至关重要，该催化活性是在温和条件下以水为反应介质的条件下实现的。这些条件的固有可持续性，再加上通过催化剂和反应介质的强健循环可实现的低E因子，证明了该技术的巨大实用性。
• [EN] INDOLE, BENZIMIDAZOLE OR BENZOTRIAZOLE DERIVATIVES INCLUDING A PIPERIDINE OR PIPERAZINE CORE AS ANTI-NEOPLASIC AGENTS OR CELL PROLIFERATION INHIBITORS<br/>[FR] DERIVES D'INDOLE, BENZIMIDAZOLE OU BENZOTRIAZOLE, COMPRENANT UN NOYAU PIPERIDINE OU PIPERAZINE, COMME AGENTS ANTI-NEOPLASIQUES OU INHIBITEURS DE PROLIFERATION CELLULAIRE
  申请人：CEREP

  公开号：WO2008107322A1

  公开（公告）日：2008-09-12

  [EN] The invention relates to compounds of the formula (I), as well as to their pharmaceutically acceptable salts, in which: Ar₁ is an aryl or heteroaryl group, each optionally substituted; X and Y are identical or different and represent a nitrogen atom of a CH group; n is an integer between 4 and 6; D is a carbon or nitrogen atom. The invention also relates to a manufacturing method, to pharmaceutical compositions containing the same, and to their use as anti-neoplasic agents and/or cell proliferation inhibitors.
  [FR] L'invention concerne des composés de formule (I) ainsi que leurs sels pharmaceutiquement acceptables, dans laquelle Ar₁ représente un groupement aryle ou hétéroaryle, chacun éventuellement substitué; X et Y, identiques ou différents, représentent un atome d'azote ou un groupement CH; n représente un nombre entier entre 4 et 6; D représente un atome de carbone ou un atome d'azote, leur procédé de fabrication, les compositions pharmaceutiques les renfermant, ainsi que leur utilisation comme agents anti-néoplasiques et/ou inhibiteurs de la prolifération cellulaire.
• Synthesis of 1-aryl indoles via coupling reaction of indoles and aryl halides catalyzed by CuI/metformin
  作者：Hu Chen、Min Lei、Lihong Hu

  DOI：10.1016/j.tet.2014.06.080

  日期：2014.9

  Ullmann-type C-N coupling reaction has been developed for the synthesis of 1-aryl indole derivatives by indoles and aryl halides in the presence of CuI/metformin (CuI/Met) in DMF. This method is very easy, rapid, and high yielding reaction for the synthesis of 1-aryl indoles. In particular, the metformin, which is used as ligand, is inexpensive and nontoxic that is considered to be relatively environmentally benign. (C) 2014 Elsevier Ltd. All rights reserved.