N-(3-bromo-5-chloro-pyridin-2-yl)-N-methyl-carbamic acid phenyl ester | 1267467-24-2

• 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: N-(3-bromo-5-chloro-pyridin-2-yl)-N-methyl-carbamic acid phenyl ester
• 英文别名: phenyl N-(3-bromo-5-chloropyridin-2-yl)-N-methylcarbamate
• CAS: 1267467-24-2
• 化学式: C₁₃H₁₀BrClN₂O₂
• 分子量: 341.592
• InChiKey: KQRXSKIMIMVYOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-bromo-5-chloro-pyridin-2-yl)-N-methyl-carbamic acid phenyl ester 在 三(三甲基硅基)硅烷 、 1,1'-偶氮(氰基环己烷) 作用下， 以 间二甲苯 为溶剂， 反应 50.0h， 以67%的产率得到(5-chloro-3-phenyl-pyridin-2-yl)-methyl-amine
  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：

  N-(3-bromo-5-chloropyridin-2-yl)pyridin-1-ium-1-aminide 在 甲酸 、 5% Pd(II)/C(eggshell) 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 65.0h， 生成 N-(3-bromo-5-chloro-pyridin-2-yl)-N-methyl-carbamic acid phenyl 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