(2S,3S)-1-(1-ethyl-3-phenyl-aziridin-2-yl)-2,2-diphenylmethanol | 1276642-49-9

• 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: (2S,3S)-1-(1-ethyl-3-phenyl-aziridin-2-yl)-2,2-diphenylmethanol
• 英文别名: [(2S,3S)-1-ethyl-3-phenylaziridin-2-yl]-diphenylmethanol
• CAS: 1276642-49-9
• 化学式: C₂₃H₂₃NO
• 分子量: 329.442
• InChiKey: NYWLHFSYBCIVKS-AJVCAZFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  23.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 氨 作用下， 以 四氢呋喃 、 环己烷 、 水 为溶剂， 反应 5.0h， 生成 (2S,3S)-1-(1-ethyl-3-phenyl-aziridin-2-yl)-2,2-diphenylmethanol
  参考文献：
  名称：

  BH₃-Promoted Stereoselective β-Lithiation of N-Alkyl-2-phenylaziridines

  摘要：

  BH3 complexes of N-alkyl-2-phenylaziridines have been synthesized land their structure and stereochemistry proved with DFT calculations and NMR experiments. It has been demonstrated that the Lewis acid complexation is able to promote a regioselective beta-lithiation in 2-phenylaziridino-borane complexes. The lithiated intermediates were configurationally stable, allowing an enantioselective preparation of cis-2,3-disubstitiited aziridines.

  DOI：

  10.1021/jo102474u

文献信息

• BH₃-Promoted Stereoselective β-Lithiation of <i>N</i>-Alkyl-2-phenylaziridines
  作者：Ugo Azzena、Giovanna Dettori、Luisa Pisano、Biagia Musio、Renzo Luisi

  DOI：10.1021/jo102474u

  日期：2011.4.1

  BH3 complexes of N-alkyl-2-phenylaziridines have been synthesized land their structure and stereochemistry proved with DFT calculations and NMR experiments. It has been demonstrated that the Lewis acid complexation is able to promote a regioselective beta-lithiation in 2-phenylaziridino-borane complexes. The lithiated intermediates were configurationally stable, allowing an enantioselective preparation of cis-2,3-disubstitiited aziridines.