2-(2,2-dibromovinyl)-5-methoxyaniline | 1290035-10-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2,2-dibromovinyl)-5-methoxyaniline
• 英文别名: 2-(2,2-Dibromoethenyl)-5-methoxyaniline
• CAS: 1290035-10-7
• 化学式: C₉H₉Br₂NO
• 分子量: 306.985
• InChiKey: VMKHJWRKVHFXRU-UHFFFAOYSA-N

物化性质

• 熔点：
  59-60 °C
• 沸点：
  385.4±42.0 °C(Predicted)
• 密度：
  1.845±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.25
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(2,2-dibromovinyl)-5-methoxyaniline 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以72%的产率得到2-bromo-6-methoxyindole
  参考文献：
  名称：

  [EN] OXA-IBOGAINE INSPIRED ANALOGUES FOR TREATMENT OF NEUROLOGICAL AND PSYCHIATRIC DISORDERS
  [FR] ANALOGUES INSPIRÉS D'OXA-IBOGAÏNE POUR LE TRAITEMENT DE TROUBLES NEUROLOGIQUES ET PSYCHIATRIQUES

  摘要：

  本发明提供了一种具有以下结构的化合物：[结构]，其中D、E、F、X1、X2和R1-R14的定义如本文所述；一种包括该化合物和药学上可接受的载体的药物组合物；以及一种治疗物质使用障碍、阿片类戒断症状、抑郁症、情绪障碍、焦虑症、帕金森病、创伤性脑损伤、头痛、偏头痛或改变心理状态或增强心理治疗效果的方法，包括向受试者施用该化合物或其药学上可接受的盐的有效量。

  公开号：

  WO2022170268A1
• 作为产物：
  描述：

  1-(2,2-dibromovinyl)-4-methoxy-2-nitrobenzene 在 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以901.1 mg的产率得到2-(2,2-dibromovinyl)-5-methoxyaniline
  参考文献：
  名称：

  Palladium-Catalyzed Synthesis of 2-Cyanoindoles from 2-gem-Dihalovinylanilines

  摘要：

  An efficient Pd(0)-catalyzed synthesis of 2-cyanoindoles from 2-gem-dihalovinylanilines is reported. Few methods have aimed to synthesize these scaffolds, which are found in many natural products and have high bioactivity. This protocol features a robust catalyst system utilizing Zn(TFA)(2) to prolong the catalytic activity. Additionally, the amount of cyanide in the reaction phase is minimized by taking advantage of the solubility of Zn(CN)(2) in a two-solvent mixture.

  DOI：

  10.1021/acs.orglett.7b02244

文献信息

• Synthesis of 3-aryl-2-aminoquinolines: palladium-catalyzed cascade reactions of gem-dibromovinylanilines with tert-butyl isocyanide and arylboronic acids
  作者：Langxi Hu、Weijun Gui、Zichen Liu、Baishan Jiang

  DOI：10.1039/c4ra05670a

  日期：——

  A three-component cascade reaction involving gem-dibromovinylanilines, tert-butyl isocyanide and arylboronic acids for the efficient synthesis of 3-aryl-2-aminoquinolines has been developed. The reaction proceeds through palladium-catalyzed isocyanide insertion, intramolecular cyclization of gem-dibromovinylanilines followed by Suzuki coupling with arylboronic acids, and the corresponding products

  为了有效合成3-芳基-2-氨基喹啉，已经开发了涉及宝石-二溴乙烯基苯胺，叔丁基异氰化物和芳基硼​​酸的三组分级联反应。通过钯催化的胩插入该反应进行，的分子内环化宝石-dibromovinylanilines随后铃木与芳基硼酸偶合，并处于良好，获得优异的分离产率相应的产品。
• Facile synthesis of 2-amino-3-bromoquinolines by palladium-catalyzed isocyanide insertion and cyclization of gem-dibromovinylanilines
  作者：Baishan Jiang、Langxi Hu、Weijun Gui

  DOI：10.1039/c4ra00821a

  日期：——

  A novel and efficient synthesis of 2-amino-3-bromoquinolines through palladium-catalyzed isocyanide insertion followed by intramolecular cyclization of gem-dibromovinylanilines was developed.

  通过钯催化的异氰酸酯插入，然后通过内环化反应合成2-氨基-3-溴喹啉的新颖高效方法已经开发出来。
• 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.
• 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.