ethyl (R)-P-((R)-1-(4-bromophenyl)-1-(1,1-dimethylethylsulfonamido)ethyl)-N-((S)-1-phenylethyl)phosphonamidate | 1410782-29-4

• 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: ethyl (R)-P-((R)-1-(4-bromophenyl)-1-(1,1-dimethylethylsulfonamido)ethyl)-N-((S)-1-phenylethyl)phosphonamidate
• 英文别名: N-[(1R)-1-(4-bromophenyl)-1-[ethoxy-[[(1S)-1-phenylethyl]amino]phosphoryl]ethyl]-2-methylpropane-2-sulfonamide
• CAS: 1410782-29-4
• 化学式: C₂₂H₃₂BrN₂O₄PS
• 分子量: 531.451
• InChiKey: AZWMELGJYCHVLN-GAAAPTCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl (R)-((R)-1-(4-bromophenyl)-1-(1,1-dimethylethylsulfonamido)ethyl)(diethoxymethyl)phosphinate 在 三氟化硼乙醚 、 溴 、 三乙胺 作用下， 以 氯仿 、 乙腈 为溶剂， 生成 ethyl (R)-P-((R)-1-(4-bromophenyl)-1-(1,1-dimethylethylsulfonamido)ethyl)-N-((S)-1-phenylethyl)phosphonamidate
  参考文献：
  名称：

  Stereospecific Transformation of Protected P–H Group into P–O or P–N Group in One-Pot Reaction

  摘要：

  A general and efficient procedure for converting 1,1-diethoxyalkylphosphinates into phosphonates or phosphonamides is described by the application of bromine with moderate to high yields and good purity in a one-pot reaction. H-Phosphinate reacts stereospecifically with bromine and subsequently couples with nucleophile to form the corresponding optically active (RP)-P-1(O)(OEt)X with retention of configuration at the phosphorus center. For alpha-amino-H-phosphinates, the transformation could be realized without the protection of the amino group.

  DOI：

  10.1021/jo302140q

文献信息

• Stereospecific Transformation of Protected P–H Group into P–O or P–N Group in One-Pot Reaction
  作者：Qiuli Yao、Chengye Yuan

  DOI：10.1021/jo302140q

  日期：2012.12.7

  A general and efficient procedure for converting 1,1-diethoxyalkylphosphinates into phosphonates or phosphonamides is described by the application of bromine with moderate to high yields and good purity in a one-pot reaction. H-Phosphinate reacts stereospecifically with bromine and subsequently couples with nucleophile to form the corresponding optically active (RP)-P-1(O)(OEt)X with retention of configuration at the phosphorus center. For alpha-amino-H-phosphinates, the transformation could be realized without the protection of the amino group.