2-(2,2-dibromovinyl)-3-chlorobenzenamine | 1190766-93-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2,2-dibromovinyl)-3-chlorobenzenamine
• CAS: 1190766-93-8
• 化学式: C₈H₆Br₂ClN
• 分子量: 311.403
• InChiKey: AHBARZPXSQAITN-UHFFFAOYSA-N

物化性质

• 沸点：
  365.3±42.0 °C(Predicted)
• 密度：
  2.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(2,2-dibromovinyl)-3-chlorobenzenamine 、 caesium carbonate 以 二甲基亚砜 为溶剂， 反应 0.17h， 以74%的产率得到2-bromo-4-chloro-1H-indole-3-carboxylic acid
  参考文献：
  名称：

  Rapid, robust, clean, catalyst-free synthesis of 2-halo-3-carboxyindoles

  摘要：

  A novel synthesis of 2-halo-3-carboxyindoles from 2-(2,2-dihalovinyl)anilines was discovered. Reaction conditions and substrate applicability were studied. Optimally, the reaction takes only minutes when these substrates are heated in DMSO at 120 degrees C in the presence of cesium carbonate. However, the reaction is robust and takes place at a wide range of temperatures, is tolerant of aqueous reaction conditions, and can be performed in a variety of polar solvent/carbonate base combinations where the limiting factor is base solubility. A wide range of substituents is tolerated on the 2-(2,2-dihalovinyl)anilines, and yields are generally high, requiring only acidic aqueous work-up to obtain pure products. No catalyst is required for the transformation. The mechanism is believed to involve initial formation of an alkynyl bromide intermediate followed by ring closure and carbon dioxide trapping, leading to product formation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.037
• 作为产物：
  描述：

  2-氯-6-硝基苯甲醛 在 三苯基膦 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(2,2-dibromovinyl)-3-chlorobenzenamine
  参考文献：
  名称：

  Rapid, robust, clean, catalyst-free synthesis of 2-halo-3-carboxyindoles

  摘要：

  A novel synthesis of 2-halo-3-carboxyindoles from 2-(2,2-dihalovinyl)anilines was discovered. Reaction conditions and substrate applicability were studied. Optimally, the reaction takes only minutes when these substrates are heated in DMSO at 120 degrees C in the presence of cesium carbonate. However, the reaction is robust and takes place at a wide range of temperatures, is tolerant of aqueous reaction conditions, and can be performed in a variety of polar solvent/carbonate base combinations where the limiting factor is base solubility. A wide range of substituents is tolerated on the 2-(2,2-dihalovinyl)anilines, and yields are generally high, requiring only acidic aqueous work-up to obtain pure products. No catalyst is required for the transformation. The mechanism is believed to involve initial formation of an alkynyl bromide intermediate followed by ring closure and carbon dioxide trapping, leading to product formation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.037

文献信息

• Palladium-Catalyzed Domino C,N-Coupling/Carbonylation/Suzuki Coupling Reaction: An Efficient Synthesis of 2-Aroyl-/Heteroaroylindoles
  作者：Martin Arthuis、Renée Pontikis、Jean-Claude Florent

  DOI：10.1021/ol901875z

  日期：2009.10.15

  A convenient one-pot synthesis of 2-aroylindoles using a domino palladium-catalyzed C,N-coupling/carbonylation/C,C-coupling sequence is described. The reaction involved easily prepared 2-gem-dibromovinylanilines and boronic acids under carbon monoxide. Optimized reaction conditions allowed the construction of a wide variety of highly functionalized 2-aroyl-/heteroaroylindoles in satisfactory yields

  描述了使用多米诺钯催化的C，N偶联/羰基化/ C，C偶联序列方便地一锅合成2-芳基吲哚。所涉及的反应容易地制备2-偕- dibromovinylanilines和硼酸下一氧化碳。优化的反应条件允许以令人满意的产率构建各种高度官能化的2-芳酰基-/杂芳酰基吲哚。
• Facile synthesis of 2-bromoindoles by ligand-free CuI-catalyzed intramolecular cross-coupling of gem-dibromoolefins
  作者：Baishan Jiang、Kemei Tao、Wang Shen、Jiancun Zhang

  DOI：10.1016/j.tetlet.2010.09.129

  日期：2010.12

  A mild and efficient synthesis of 2-bromoindoles by ligand-free CuI-catalyzed intramolecular cross-coupling of gem-dibromoolefins was developed. Reactions were carried out in toluene at room temperature and the corresponding 2-bromoindoles were obtained in excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.