(S)-3-(diethylphosphoryl)-3-phenyl-1-pyrrol-1-yl-propan-1-one | 1221726-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (S)-3-(diethylphosphoryl)-3-phenyl-1-pyrrol-1-yl-propan-1-one
• 英文别名: (3S)-3-diethylphosphoryl-3-phenyl-1-pyrrol-1-ylpropan-1-one
• CAS: 1221726-75-5
• 化学式: C₁₇H₂₂NO₂P
• 分子量: 303.341
• InChiKey: DHSSDPTXZFRJAC-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  39.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-(diethylphosphoryl)-3-phenyl-1-pyrrol-1-yl-propan-1-one 在 三氯硅烷 、 三乙胺 、 dimethyl sulfide borane 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以76%的产率得到
  参考文献：
  名称：

  Catalytic Asymmetric Hydrophosphinylation of α,β-Unsaturated N-Acylpyrroles: Application of Dialkyl Phosphine Oxides in Enantioselective Synthesis of Chiral Phosphine Oxides or Phosphines

  摘要：

  Dialkyl phosphine oxides were introduced in catalytic asymmetric transformations for the first time. An unprecedented phospha-Michael reaction of dialkyl phosphine oxide with alpha,beta-unsaturated N-acylpyrroles was disclosed. Excellent enantioselectivities (94-99% ee) and chemical yields (up to 99%) were achieved with a broad substrate scope of the N-acylpyrroles. Importantly, pyridine was found to be critical to achieve good results for the present reaction.

  DOI：

  10.1021/ol100504h
• 作为产物：
  描述：

  diethylphosphine oxide 、 3-phenyl-1-pyrrol-1-yl-2-propen-1-one 在 吡啶 、 Dimethylzinc 、 (S,S)-(+)-2,6-双[2-(羟基二苯甲基)-1-吡咯烷基-甲基]-4-甲基苯酚 作用下， 以 甲苯 为溶剂， 以99%的产率得到(S)-3-(diethylphosphoryl)-3-phenyl-1-pyrrol-1-yl-propan-1-one
  参考文献：
  名称：

  Catalytic Asymmetric Hydrophosphinylation of α,β-Unsaturated N-Acylpyrroles: Application of Dialkyl Phosphine Oxides in Enantioselective Synthesis of Chiral Phosphine Oxides or Phosphines

  摘要：

  Dialkyl phosphine oxides were introduced in catalytic asymmetric transformations for the first time. An unprecedented phospha-Michael reaction of dialkyl phosphine oxide with alpha,beta-unsaturated N-acylpyrroles was disclosed. Excellent enantioselectivities (94-99% ee) and chemical yields (up to 99%) were achieved with a broad substrate scope of the N-acylpyrroles. Importantly, pyridine was found to be critical to achieve good results for the present reaction.

  DOI：

  10.1021/ol100504h

文献信息

• Catalytic Asymmetric Hydrophosphinylation of α,β-Unsaturated <i>N</i>-Acylpyrroles: Application of Dialkyl Phosphine Oxides in Enantioselective Synthesis of Chiral Phosphine Oxides or Phosphines
  作者：Depeng Zhao、Lijuan Mao、Yuan Wang、Dongxu Yang、Quanliang Zhang、Rui Wang

  DOI：10.1021/ol100504h

  日期：2010.4.16

  Dialkyl phosphine oxides were introduced in catalytic asymmetric transformations for the first time. An unprecedented phospha-Michael reaction of dialkyl phosphine oxide with alpha,beta-unsaturated N-acylpyrroles was disclosed. Excellent enantioselectivities (94-99% ee) and chemical yields (up to 99%) were achieved with a broad substrate scope of the N-acylpyrroles. Importantly, pyridine was found to be critical to achieve good results for the present reaction.