2-phenylquinolin-3-yl N,N,N',N'-tetramethyldiamidophosphate | 1224598-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-phenylquinolin-3-yl N,N,N',N'-tetramethyldiamidophosphate
• 英文别名: N-[dimethylamino-oxido-(2-phenylquinolin-3-yl)oxyphosphaniumyl]-N-methylmethanamine
• CAS: 1224598-14-4
• 化学式: C₁₉H₂₂N₃O₂P
• 分子量: 355.376
• InChiKey: GOLHKGIJNNGXDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-phenylquinolin-3-yl N,N,N',N'-tetramethyldiamidophosphate 、 氰基甲酸乙酯 在 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到ethyl 3-([bis(dimethylamino)phosphoryl]oxy)-2-phenylquinoline-4-carboxylate
  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：

  碘苯 、 quinolin-3-yl N,N,N',N'-tetramethyldiamidophosphate 在 bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex 、 zinc(II) chloride 、 三(2-呋喃基)膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以81%的产率得到2-phenylquinolin-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.