N-[(3-bromo-5-chloro-pyridin-2-yl)-naphthalen-1-yloxycarbonyl-amino]pyridinium chloride | 1267467-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[(3-bromo-5-chloro-pyridin-2-yl)-naphthalen-1-yloxycarbonyl-amino]pyridinium chloride
• 英文别名: naphthalen-1-yl N-(3-bromo-5-chloropyridin-2-yl)-N-pyridin-1-ium-1-ylcarbamate;chloride
• CAS: 1267467-16-2
• 化学式: C₂₁H₁₄BrClN₃O₂*Cl
• 分子量: 491.171
• InChiKey: QDQAIXSGJGKODR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(3-bromo-5-chloro-pyridin-2-yl)-naphthalen-1-yloxycarbonyl-amino]pyridinium chloride 在 三乙基硼 作用下， 以 乙醇 、 正己烷 为溶剂， 以25%的产率得到N-(3-bromo-5-chloro-pyridin-2-yl)carbamic acid naphthalen-1-yl ester
  参考文献：
  名称：

  Unusual Approach to 3-Aryl-2-aminopyridines through a Radical Mechanism: Synthesis and Theoretical Rationale from Quantum Mechanical Calculations

  摘要：

  Tris(trimethylsilyl)silane and azobis(cyclohexanenitrile) promoted the easy intramolecular arylation of aryl bromopyridine carbamates through a radical [1,6] ipso substitution process. These substrates showed a preference for this type of reaction over the alternative [1,7] addition. The results were rationalized by making use of quantum mechanical calculations and computer graphics.

  DOI：

  10.1021/jo102122h
• 作为产物：
  描述：

  氯甲酸-1-萘酯 、 N-(3-bromo-5-chloropyridin-2-yl)pyridin-1-ium-1-aminide 以 丙酮 为溶剂， 反应 0.17h， 以90%的产率得到N-[(3-bromo-5-chloro-pyridin-2-yl)-naphthalen-1-yloxycarbonyl-amino]pyridinium chloride
  参考文献：
  名称：

  Unusual Approach to 3-Aryl-2-aminopyridines through a Radical Mechanism: Synthesis and Theoretical Rationale from Quantum Mechanical Calculations

  摘要：

  Tris(trimethylsilyl)silane and azobis(cyclohexanenitrile) promoted the easy intramolecular arylation of aryl bromopyridine carbamates through a radical [1,6] ipso substitution process. These substrates showed a preference for this type of reaction over the alternative [1,7] addition. The results were rationalized by making use of quantum mechanical calculations and computer graphics.

  DOI：

  10.1021/jo102122h

文献信息

• Unusual Approach to 3-Aryl-2-aminopyridines through a Radical Mechanism: Synthesis and Theoretical Rationale from Quantum Mechanical Calculations
  作者：Marta Camacho-Artacho、Valentina Abet、Luis M. Frutos、Federico Gago、Julio Alvarez-Builla、Carolina Burgos

  DOI：10.1021/jo102122h

  日期：2011.3.4

  Tris(trimethylsilyl)silane and azobis(cyclohexanenitrile) promoted the easy intramolecular arylation of aryl bromopyridine carbamates through a radical [1,6] ipso substitution process. These substrates showed a preference for this type of reaction over the alternative [1,7] addition. The results were rationalized by making use of quantum mechanical calculations and computer graphics.