3,5-dibromo-2-fluorobenzenamine | 1404196-11-7

• 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: 3,5-dibromo-2-fluorobenzenamine
• 英文别名: 3,5-dibromo-2-fluorophenylamine；3,5-dibromo-2-fluoroaniline
• CAS: 1404196-11-7
• 化学式: C₆H₄Br₂FN
• 分子量: 268.911
• InChiKey: LDLPMCQQIHVTEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-dibromo-2-fluorobenzenamine 、 4-methoxy-3-(4-(2,2,2-trichloroacetyl)piperazin-1-yl)benzene-1-sulfonyl chloride 在 吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 N-(3,5-Dibromo-2-fluoro-phenyl)-4-methoxy-3-[4-(2,2,2-trichloro-acetyl)-piperazin-1-yl]-benzenesulfonamide
  参考文献：
  名称：

  Phenyl benzenesulfonamides are novel and selective 5-HT6 antagonists: identification of N-(2,5-dibromo-3-fluorophenyl)-4-methoxy-3-piperazin-1-ylbenzenesulfonamide (SB-357134)

  摘要：

  Substituted N-phenyl-4-methoxy-3-piperazin-1-ylbenzenesulfonamides and conformationally restricted analogues have been identified as high affinity and selective 5-HT6 antagonists. Compounds from this series had a range of pharmacokinetic profiles in rat and in general there was a correlation between clearance and CNS penetration. Based on its overall biological profile 2 (SB-357134) was selected for further pre-clinical evaluation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00597-7
• 作为产物：
  描述：

  3,5-二溴-2-氟苯硼酸 在 2,4-二硝基苯基羟胺 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以54%的产率得到3,5-dibromo-2-fluorobenzenamine
  参考文献：
  名称：

  Elusive Metal-Free Primary Amination of Arylboronic Acids: Synthetic Studies and Mechanism by Density Functional Theory

  摘要：

  Herein, we disclose the first metal-free synthesis of primary aromatic amines from arylboronic acids, a reaction that has eluded synthetic chemists for decades. This remarkable transformation affords structurally diverse primary arylamines in good chemical yields, including a variety of halogenated primary anilines that often cannot be prepared via transition-metal-catalyzed amination. The reaction is operationally simple, requires only a slight excess of aminating agent, proceeds under neutral or basic conditions, and, importantly, can be scaled up to provide multigram quantities of primary anilines. Density functional calculations reveal that the most likely mechanism involves a facile 1,2-aryl migration and that the presence of an ortho nitro group in the aminating agent plays a critical role in lowering the free energy barrier of the 1,2-aryl migration step.

  DOI：

  10.1021/ja309637r