methyl (2S,3'R)-2-(3-fluoro-2,2-diphenylaziridin-1-yl)-3-phenylpropanoate | 1245904-20-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S,3'R)-2-(3-fluoro-2,2-diphenylaziridin-1-yl)-3-phenylpropanoate
• CAS: 1245904-20-4
• 化学式: C₂₄H₂₂FNO₂
• 分子量: 375.443
• InChiKey: NPORVBZEBKOSLU-OYICLKKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.31
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,3'R)-2-(3-fluoro-2,2-diphenylaziridin-1-yl)-3-phenylpropanoate 在 三氟化锑 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl (S)-2-[(2-fluoro-2,2-diphenylethylidene)amino]-3-phenylpropanoate
  参考文献：
  名称：

  Monofluorinated aziridines in asymmetric synthesis of chiral fluorinated prop-2-yn-1-amines

  摘要：

  Nonracemic C-fluoroaziridines were synthesized for the first time by reaction of fluorocarbene with N-diphenylmethylidene-substituted natural amino acid esters. The products were shown to be used in asymmetric synthesis of chiral fluorinated prop-2-yn-1-amines via one-pot process involving isomerization of 2-fluoroaziridines into alpha-fluoro imines and subsequent reaction with alkynyldifluoroborane generated in situ.

  DOI：

  10.1134/s1070428010070043
• 作为产物：
  描述：

  二溴氟甲烷 、 L-苯丙氨酸,N-(二苯亚甲基)-,甲基酯 在 lead 、 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 77.0h， 以22%的产率得到methyl (2S,3'R)-2-(3-fluoro-2,2-diphenylaziridin-1-yl)-3-phenylpropanoate
  参考文献：
  名称：

  Monofluorinated aziridines in asymmetric synthesis of chiral fluorinated prop-2-yn-1-amines

  摘要：

  Nonracemic C-fluoroaziridines were synthesized for the first time by reaction of fluorocarbene with N-diphenylmethylidene-substituted natural amino acid esters. The products were shown to be used in asymmetric synthesis of chiral fluorinated prop-2-yn-1-amines via one-pot process involving isomerization of 2-fluoroaziridines into alpha-fluoro imines and subsequent reaction with alkynyldifluoroborane generated in situ.

  DOI：

  10.1134/s1070428010070043