diethyl (S)-hydroxy{(S)-1-[(S)-1-phenylethyl]aziridin-2-yl}methylphosphonate | 945676-55-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl (S)-hydroxy{(S)-1-[(S)-1-phenylethyl]aziridin-2-yl}methylphosphonate
• CAS: 945676-55-1
• 化学式: C₁₅H₂₄NO₄P
• 分子量: 313.334
• InChiKey: CVYCJPOAEHCHPZ-UGEFFSKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.77
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diethyl (S)-hydroxy{(S)-1-[(S)-1-phenylethyl]aziridin-2-yl}methylphosphonate 在 palladium dihydroxide 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 88.0h， 生成 diethyl (1S,2S)-2-acetamido-1-hydroxypropylphosphonate
  参考文献：
  名称：

  Synthesis of four enantiomers of 2-acetamido-1-hydroxypropylphosphonates

  摘要：

  Enantiomerically pure diethyl 2-acetamido-1-hydroxypropylphosphonates were synthesised from N-[(R)-(1-phenylethyl)]aziridine-(2S)- and N-[(S)-(1-phenylethyl)]aziridine-(2R)-carboxaldehydes via phosphonylation followed by acetylation of the hydroxy groups and the simultaneous hydrogenolytic cleavage of the aziridine rings and the removal of the chiral auxiliaries. In addition, enantiomerically pure diethyl (1S,2R)- and (1R,2S)-2-amino-1-hydroxypropylphosphonates (the phosphonate analogues of isothreonine) were separated. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.021
• 作为产物：
  描述：

  N-[(S)-α-phenylethyl]aziridin-2(S)-yl-methanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 反应 73.0h， 生成 diethyl (S)-hydroxy{(S)-1-[(S)-1-phenylethyl]aziridin-2-yl}methylphosphonate
  参考文献：
  名称：

  Synthesis of four enantiomers of 2-acetamido-1-hydroxypropylphosphonates

  摘要：

  Enantiomerically pure diethyl 2-acetamido-1-hydroxypropylphosphonates were synthesised from N-[(R)-(1-phenylethyl)]aziridine-(2S)- and N-[(S)-(1-phenylethyl)]aziridine-(2R)-carboxaldehydes via phosphonylation followed by acetylation of the hydroxy groups and the simultaneous hydrogenolytic cleavage of the aziridine rings and the removal of the chiral auxiliaries. In addition, enantiomerically pure diethyl (1S,2R)- and (1R,2S)-2-amino-1-hydroxypropylphosphonates (the phosphonate analogues of isothreonine) were separated. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.021