P,P-diphenyl-N-(1-phenylprop-2-ynyl)phosphinic amide | 1187086-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: P,P-diphenyl-N-(1-phenylprop-2-ynyl)phosphinic amide
• 英文别名: (1R)-N-diphenylphosphoryl-1-phenylprop-2-yn-1-amine
• CAS: 1187086-76-5
• 化学式: C₂₁H₁₈NOP
• 分子量: 331.354
• InChiKey: QPHSSJOCURREKM-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  P,P-diphenyl-N-(1-phenylprop-2-ynyl)phosphinic amide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以73%的产率得到N-(1-phenylpropyl)-diphenylphosphinamide
  参考文献：
  名称：

  Enantioselective Nucleophilic Addition of Trimethylsilylacetylene to N-Phosphinoylimines Promoted by C₂-Symmetric Proline-Derived β-Amino Alcohol

  摘要：

  Both C-2- and C-3-symmetric proline-derived beta-amine alcohol ligands were designed, synthesized, and successfully applied to the enantioselective direct addition of trimethylsilylacetylene to N-phosphinoylimines. Aromatic, heteroaromatic, and aliphatic N-(diphenylphosphinoyl) imines and several N-(diethoxyphosphoryl) imines were tested, and optically active propargylic amides in good yields (up to 92%) and excellent enantioselectivities (up to 95%) were obtained by the simple experimental procedure. The convenience, mild conditions, and easy deprotection of the phosphonamide products made the present method very attractive. Furthermore, the Michael-type addition process of C=N alkynylation was studied and proposed on the basis of React P-31 NMR investigation.

  DOI：

  10.1021/jo901492w
• 作为产物：
  描述：

  (S)-P,P-diphenyl-N-(1-phenyl-3-(trimethylsilyl)prop-2-ynyl)phosphinic amide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以87%的产率得到P,P-diphenyl-N-(1-phenylprop-2-ynyl)phosphinic amide
  参考文献：
  名称：

  Enantioselective Nucleophilic Addition of Trimethylsilylacetylene to N-Phosphinoylimines Promoted by C₂-Symmetric Proline-Derived β-Amino Alcohol

  摘要：

  Both C-2- and C-3-symmetric proline-derived beta-amine alcohol ligands were designed, synthesized, and successfully applied to the enantioselective direct addition of trimethylsilylacetylene to N-phosphinoylimines. Aromatic, heteroaromatic, and aliphatic N-(diphenylphosphinoyl) imines and several N-(diethoxyphosphoryl) imines were tested, and optically active propargylic amides in good yields (up to 92%) and excellent enantioselectivities (up to 95%) were obtained by the simple experimental procedure. The convenience, mild conditions, and easy deprotection of the phosphonamide products made the present method very attractive. Furthermore, the Michael-type addition process of C=N alkynylation was studied and proposed on the basis of React P-31 NMR investigation.

  DOI：

  10.1021/jo901492w

文献信息

• Enantioselective Nucleophilic Addition of Trimethylsilylacetylene to <i>N</i>-Phosphinoylimines Promoted by <i>C</i>₂-Symmetric Proline-Derived β-Amino Alcohol
  作者：Shaoqun Zhu、Wenjin Yan、Bin Mao、Xianxing Jiang、Rui Wang

  DOI：10.1021/jo901492w

  日期：2009.9.18

  Both C-2- and C-3-symmetric proline-derived beta-amine alcohol ligands were designed, synthesized, and successfully applied to the enantioselective direct addition of trimethylsilylacetylene to N-phosphinoylimines. Aromatic, heteroaromatic, and aliphatic N-(diphenylphosphinoyl) imines and several N-(diethoxyphosphoryl) imines were tested, and optically active propargylic amides in good yields (up to 92%) and excellent enantioselectivities (up to 95%) were obtained by the simple experimental procedure. The convenience, mild conditions, and easy deprotection of the phosphonamide products made the present method very attractive. Furthermore, the Michael-type addition process of C=N alkynylation was studied and proposed on the basis of React P-31 NMR investigation.