2-(2,4-dichlorophenyl)-1H-indole | 76869-15-3

• 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: 2-(2,4-dichlorophenyl)-1H-indole
• CAS: 76869-15-3
• 化学式: C₁₄H₉Cl₂N
• mdl: MFCD05224900
• 分子量: 262.138
• InChiKey: ZFEKXOOYILRYEW-UHFFFAOYSA-N

物化性质

• 沸点：
  425.0±30.0 °C(Predicted)
• 密度：
  1.371±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(2,4-dichlorophenyl)-1H-indole 在 ammonium hydroxide 、 氧气 、 copper(I) bromide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以63%的产率得到2-(2,4-dichlorophenyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Copper-Catalyzed Synthesis of 2-Arylquinazolinones from 2-Arylindoles with Amines or Ammoniums

  摘要：

  A novel copper-catalyzed synthesis of quinazolinones from easily available 2-arylindoles and amines or ammoniums has been developed, which provided various quinazolinones in up to 99% yields for 43 examples. This strategy features tolerance of a wide range of functional groups, easily available starting materials, simple operation, mild reaction conditions, and environmental friendliness.

  DOI：

  10.1021/acs.joc.5b00957

文献信息

• Easy access to 3-indolyl 1,1,2,2-ethanetetracarboxylates from malonates and indoles catalyzed by Pd(OAc)2
  作者：Yunqi Liu、Xiangdong Wang、Lianhui Wang、Jinhai Shen、Yadong Feng、Xiuling Cui

  DOI：10.1016/j.tet.2016.10.042

  日期：2016.12

  A novel dehydrodimerization of malonates with indoles has been developed, providing simple and rapid access to 3-indolyl tetramethyl 1,1,2,2-ethanetetracarboxylates. Pd(OAc)2-catalyzed ‘one pot’ C(sp2)–C(sp3) and C(sp3)–C(sp3) cross-dehydrogenative-couplings of malonates with a variety of 2-aryl indoles were involved. The titled compounds were obtained in high yields with good functional group tolerance

  已经开发了丙二酸酯与吲哚的新型脱氢二聚，其提供了简单快速地获得3-吲哚基四甲基1,1,2,2-乙烷四羧酸酯。Pd（OAc）2催化的“一锅” C（sp 2）–C（sp 3）和C（sp 3）–C（sp 3）丙二酸酯与各种2-芳基吲哚的交叉脱氢偶联分别为参与。以高收率获得具有良好官能团耐受性的标题化合物。
• Copper‐Catalyzed Aerobic Cross‐Dehydrogenative Coupling of β‐Oxime Ether Furan with Indole
  作者：Rushil Fernandes、Krishna Mhaske、Reena Balhara、Garima Jindal、Rishikesh Narayan

  DOI：10.1002/asia.202101369

  日期：2022.3.14

  Furan and Indole represent two of the most versatile heterocycles in organic chemistry. Herein, we report the first cross-dehydrogenative coupling of these two heterocycles catalyzed by copper in combination with aerial oxygen. Additionally, we also demonstrate a lesser known activating group effect of oxime ether substituent in oxidative coupling. The reaction has broad substrate scope and exhibits

  呋喃和吲哚代表有机化学中用途最广泛的两种杂环。在此，我们报告了铜与空气氧结合催化的这两个杂环的首次交叉脱氢偶联。此外，我们还证明了肟醚取代基在氧化偶联中鲜为人知的活化基团效应。该反应具有广泛的底物范围和优异的化学选择性。
• 一种喹唑啉酮芳香化合物的合成方法
  申请人：华侨大学

  公开号：CN104496915B

  公开（公告）日：2017-05-03

  本发明公开了一种喹唑啉酮芳香化合物的合成方法，将2‑芳基吲哚、有机胺/无机铵和溴化亚铜溶于有机溶剂中，在氧气参与条件下，于60‑120℃反应20～30小时后，经分离纯化，即得所述喹唑啉酮芳香化合物。本发明的合成方法的原料易得，收率高(高达99％)；反应条件温和，反应时间短，底物范围广，反应专一性强,后处理简便且绿色。
• Synthesis of 3‐Arylazoindoles through Iron(III)‐Catalyzed C−H Azolation of Indoles and Arylhydrazines
  作者：Kun Li、Jin‐Qi Zhang、Wei‐Cong Liao、Cui Liang、Xiao‐Pan Ma、Dong‐Liang Mo、Chun‐Hua Chen

  DOI：10.1002/adsc.202301388

  日期：——

  A variety of functionalized 3‐arylazoindoles were prepared in good to excellent yields through an iron(III)‐catalyzed C‐H azolation of 2‐substituted indoles with arylhydrazines under mild reaction conditions. The reaction underwent an initial TBN‐mediated nitrosation, 1,5‐hydrogen migration, intramolecular condensation, and 1,5‐hydrogen migration over four steps in one pot. A paracyclophane‐derived

  在温和的反应条件下，通过铁(III)催化的2-取代吲哚与芳基肼的C-H偶氮化反应，以良好至优异的收率制备了各种官能化的3-芳基偶氮吲哚。该反应在一锅中经历了初始 TBN 介导的亚硝化、1,5-氢迁移、分子内缩合和 1,5-氢迁移四个步骤。经过三个步骤可以以 25% 的产率制备对环芳烷衍生的 3-苯基偶氮吲哚，并且一些制备的 3-芳基偶氮吲哚表现出不同的荧光发射波长，并且存在明显的 pH 条件响应。该方法突出了易于获得的起始原料的广泛底物范围、广泛的官能团兼容性、克级规模的制备、高原子经济性、避免不稳定和爆炸性的偶氮化试剂以及通过萃取、洗涤和重结晶而无需闪蒸柱的简单纯化操作色谱法。
• Regioselective one pot synthesis of 3,3′-diindolylethylene derivatives and study of their cytotoxic activity
  作者：Madhumita Mandal、Deepak Kumar、Rajneeta Roy、Rupashree Sen、Padma Das、Mitali Chatterjee、Parasuraman Jaisankar

  DOI：10.1016/j.bmcl.2011.03.028

  日期：2011.5

  2,2'-Diphenyl-3,3'-diindolylethylene (DPDIE) derivatives 3a-g were regioselectively prepared in one pot from indoles 1a-g in the presence of Lewis acids and were subsequently evaluated for cytotoxic activity against human leukemic cell lines, U937 and K562. The most potent compound 3g exhibited IC50 of 13.0-17.0 mu M. (C) 2011 Elsevier Ltd. All rights reserved.