[2-(6-bromopyridin-2-yl)ethyl]phosphoramidic acid diethyl ester | 404034-93-1

• 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: [2-(6-bromopyridin-2-yl)ethyl]phosphoramidic acid diethyl ester
• 英文别名: 2-(6-bromopyridin-2-yl)-N-diethoxyphosphorylethanamine
• CAS: 404034-93-1
• 化学式: C₁₁H₁₈BrN₂O₃P
• 分子量: 337.153
• InChiKey: AYABLSBAMOWZBB-UHFFFAOYSA-N

物化性质

• 沸点：
  397.8±52.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  (4-cyanobutyl)zinc iodide 、 [2-(6-bromopyridin-2-yl)ethyl]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77%的产率得到{2-[6-(4-cyanobutyl)pyridin-2-yl]ethyl}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：

  (6-溴吡啶-2-基)乙腈 在 三氟化硼四氢呋喃络合物 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 [2-(6-bromopyridin-2-yl)ethyl]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

文献信息

• Palladium(0)-Catalyzed Coupling of Organozinc Iodide Reagents with Bromopyridines:  Synthesis of Selectively Protected Pyridine-Containing Azamacrocycles
  作者：Renato T. Skerlj、Yuanxi Zhou、Trevor Wilson、Gary J. Bridger

  DOI：10.1021/jo0109523

  日期：2002.2.1

  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.