N-[diethoxy(oxido)phosphaniumyl]-1-naphthalen-2-ylmethanimine | 1187086-75-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[diethoxy(oxido)phosphaniumyl]-1-naphthalen-2-ylmethanimine
• CAS: 1187086-75-4
• 化学式: C₁₅H₁₈NO₃P
• 分子量: 291.287
• InChiKey: BFZOOKMGUDHKBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  53.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[diethoxy(oxido)phosphaniumyl]-1-naphthalen-2-ylmethanimine 、 三甲基乙炔基硅 在 (2S,2S')-1,1'-(5-methyl-1,3-phenylene)bis(methylene)bis(pyrrolidin-2-ylmethanol) 、 diethylzinc 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 diethyl 1-(naphthalen-2-yl)-3-(trimethylsilyl)prop-2-ynylphosphoramidate 、 diethyl 1-(naphthalen-2-yl)-3-(trimethylsilyl)prop-2-ynylphosphoramidate
  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