N-(6-bromopyridin-2-ylmethyl)phosphoramidic acid diethyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: N-(6-bromopyridin-2-ylmethyl)phosphoramidic acid diethyl ester
• 英文别名: 1-(6-bromopyridin-2-yl)-N-diethoxyphosphorylmethanamine
• 化学式: C₁₀H₁₆BrN₂O₃P
• 分子量: 323.126
• InChiKey: NYFFPYUCCCYRCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-cyanopentylzinc iodide 、 N-(6-bromopyridin-2-ylmethyl)phosphoramidic acid diethyl ester 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以95%的产率得到{2-[6-(5-cyanopentyl)pyridin-2-yl]methyl}phosphoramidic acid diethyl ester
  参考文献：
  名称：

  Palladium(0)-Catalyzed Coupling of Organozinc Iodide Reagents with Bromopyridines:  Synthesis of Selectively Protected Pyridine-Containing Azamacrocycles

  摘要：

  The synthesis of azamacrocycles in which the ring nitrogens are regioselectively functionalized is described. An organozinc palladium(0)-catalyzed coupling with an appropriately functionalized bromopyridine generated a key intermediate, which was transformed in two steps to a desired precursor and subjected to an intramolecular N-alkylation to effect a macrocyclization affording selectively protected azamacrocycles 1-3.

  DOI：

  10.1021/jo0109523
• 作为产物：
  描述：

  氯磷酸二乙酯 、 6-溴-2-吡啶甲胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到N-(6-bromopyridin-2-ylmethyl)phosphoramidic acid diethyl ester
  参考文献：
  名称：

  Palladium(0)-Catalyzed Coupling of Organozinc Iodide Reagents with Bromopyridines:  Synthesis of Selectively Protected Pyridine-Containing Azamacrocycles

  摘要：

  The synthesis of azamacrocycles in which the ring nitrogens are regioselectively functionalized is described. An organozinc palladium(0)-catalyzed coupling with an appropriately functionalized bromopyridine generated a key intermediate, which was transformed in two steps to a desired precursor and subjected to an intramolecular N-alkylation to effect a macrocyclization affording selectively protected azamacrocycles 1-3.

  DOI：

  10.1021/jo0109523