3-[4-(methylthio)phenyl]pyridin-2-yl N,N,N',N'-tetramethyldiamidophosphate | 1224597-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-[4-(methylthio)phenyl]pyridin-2-yl N,N,N',N'-tetramethyldiamidophosphate
• 英文别名: N-[dimethylamino-[3-(4-methylsulfanylphenyl)pyridin-2-yl]oxyphosphoryl]-N-methylmethanamine
• CAS: 1224597-95-8
• 化学式: C₁₆H₂₂N₃O₂PS
• 分子量: 351.409
• InChiKey: ZKDFMLFZCRNKEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  71
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-溴茴香硫醚 、 pyridin-2-yl N,N,N',N'-tetramethyldiamidophosphate 在 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex 、 zinc(II) chloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以74%的产率得到3-[4-(methylthio)phenyl]pyridin-2-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.