1-(2,2-Dibromo-vinyl)-3-methoxy-2-nitro-benzene | 959143-07-8

• 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: 1-(2,2-Dibromo-vinyl)-3-methoxy-2-nitro-benzene
• CAS: 959143-07-8
• 化学式: C₉H₇Br₂NO₃
• 分子量: 336.967
• InChiKey: KUNHVVNAKDUHBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(2,2-Dibromo-vinyl)-3-methoxy-2-nitro-benzene 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 0.75h， 生成 2-(2,2-二溴-乙烯基)-6-甲氧基-苯基胺
  参考文献：
  名称：

  CuI-Catalyzed Tandem Intramolecular Amidation Using gem-Dibromovinyl Systems

  摘要：

  Imidazoindolones are present as the key structural motif in the family of antifungals, fumiquinazolines, and the antagonist asperlicin. The first example of a Cul-catalyzed tandem intramolecular amidation forming substituted imidazoindolones from readily accessible ortho gem-dibromovinylanilines is described.

  DOI：

  10.1021/ol052840u
• 作为产物：
  描述：

  四溴化碳 、 3-甲氧基-2-硝基苯甲醛 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以92%的产率得到1-(2,2-Dibromo-vinyl)-3-methoxy-2-nitro-benzene
  参考文献：
  名称：

  WO2007/134421

  摘要：

  公开号：

文献信息

• Rapid, robust, clean, catalyst-free synthesis of 2-halo-3-carboxyindoles
  作者：Aaron R. Kunzer、Michael D. Wendt

  DOI：10.1016/j.tetlet.2011.02.037

  日期：2011.4

  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.
• Tandem Palladium-Catalyzed N,C-Coupling/Carbonylation Sequence for the Synthesis of 2-Carboxyindoles
  作者：Tiago O. Vieira、Laura A. Meaney、Yong-Ling Shi、Howard Alper

  DOI：10.1021/ol801985q

  日期：2008.11.6

  Tandem palladium-catalyzed N,C-coupling/carbonylation, under 10 atm of carbon monoxide and at 110 degrees C, is a novel and efficient method for the preparation of 2-carboxyindoles. The catalyst system tolerates a variety of functional groups, and the noted indoles were obtained in good isolated yields.