pyridin-3-yl N,N,N',N'-tetramethyldiamidophosphate | 1224597-88-9

• 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: pyridin-3-yl N,N,N',N'-tetramethyldiamidophosphate
• 英文别名: N-[dimethylamino(pyridin-3-yloxy)phosphoryl]-N-methylmethanamine
• CAS: 1224597-88-9
• 化学式: C₉H₁₆N₃O₂P
• 分子量: 229.219
• InChiKey: PATVXGZFMVBMFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  45.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-溴-2-甲基丙烯 、 pyridin-3-yl N,N,N',N'-tetramethyldiamidophosphate 在 bis(2,2,6,6-tetramethylpiperidinyl)zinc, lithium chloride, magnesium chloride complex 、 copper(I) cyanide di(lithium chloride) 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到4-(2-methylprop-2-en-1-yl)pyridin-3-yl N,N,N',N'-tetramethyldiamidophosphate
  参考文献：
  名称：

  Phosphorodiamidate-Directed Metalation of N-Heterocycles using Mg- and Zn-TMP Bases

  摘要：

  The strong directing ability of the N,N,N',N'-tetramethyldiaminophosphorodiamidate group has been used to achieve selective metalations on various heterocycles such as pyridines, quinolines and quinoxalines with TMP-derived bases like TMPMgCl.LiCl, TMP2Mg.2LiCl, and TMP2Zn.2MgCl(2).2LiCl. This protocol was applied in the synthesis of etoricoxib, talnetant and a P-selectin inhibitor.

  DOI：

  10.1021/ol100453x
• 作为产物：
  描述：

  3-羟基吡啶 、 双(二甲胺基)氯酸磷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以88%的产率得到pyridin-3-yl N,N,N',N'-tetramethyldiamidophosphate
  参考文献：
  名称：

  Phosphorodiamidate-Directed Metalation of N-Heterocycles using Mg- and Zn-TMP Bases

  摘要：

  The strong directing ability of the N,N,N',N'-tetramethyldiaminophosphorodiamidate group has been used to achieve selective metalations on various heterocycles such as pyridines, quinolines and quinoxalines with TMP-derived bases like TMPMgCl.LiCl, TMP2Mg.2LiCl, and TMP2Zn.2MgCl(2).2LiCl. This protocol was applied in the synthesis of etoricoxib, talnetant and a P-selectin inhibitor.

  DOI：

  10.1021/ol100453x

文献信息

• Phosphorodiamidate-Directed Metalation of <i>N</i>-Heterocycles using Mg- and Zn-TMP Bases
  作者：Christoph J. Rohbogner、Stefan Wirth、Paul Knochel

  DOI：10.1021/ol100453x

  日期：2010.5.7

  The strong directing ability of the N,N,N',N'-tetramethyldiaminophosphorodiamidate group has been used to achieve selective metalations on various heterocycles such as pyridines, quinolines and quinoxalines with TMP-derived bases like TMPMgCl.LiCl, TMP2Mg.2LiCl, and TMP2Zn.2MgCl(2).2LiCl. This protocol was applied in the synthesis of etoricoxib, talnetant and a P-selectin inhibitor.