tert-butyl (S)-2-formylaziridine-1-carboxylate | 1171118-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丙烷
• 英文名称: tert-butyl (S)-2-formylaziridine-1-carboxylate
• 英文别名: tert-butyl (2S)-2-formylaziridine-1-carboxylate
• CAS: 1171118-67-4
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: QBPYTROGYKSHBW-AADKRJSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2-formylaziridine-1-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 tert-butyl (S)-2-(hydroxymethyl)aziridine-1-carboxylate
  参考文献：
  名称：

  Enantioselective aziridination reaction of α,β-unsaturated aldehydes using an organocatalyst and tert-butyl N-arenesulfonyloxycarbamates

  摘要：

  An organocatalytic enantioselective aziridination reaction of alpha,beta-unsaturated aldehydes including aromatic substrates using N-arenesulfonyloxycarbamates in the presence of diphenylprolinol triethylsilyl ether and sodium carbonate or sodium acetate is described.

  DOI：

  10.1016/j.tetlet.2009.02.095
• 作为产物：
  描述：

  tert-butyl (S)-2-(hydroxymethyl)aziridine-1-carboxylate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以80%的产率得到tert-butyl (S)-2-formylaziridine-1-carboxylate
  参考文献：
  名称：

  Asymmetric Total Syntheses of (−)-Renieramycin M and G and (−)-Jorumycin Using Aziridine as a Lynchpin

  摘要：

  By exploring the triple reactivity of two aziridines and double nucleophilicity of two aromatics, convergent and versatile syntheses of the above four natural products were developed.

  DOI：

  10.1021/ol9024919

文献信息

• Enantioselective aziridination reaction of α,β-unsaturated aldehydes using an organocatalyst and tert-butyl N-arenesulfonyloxycarbamates
  作者：Hiromi Arai、Naomi Sugaya、Neri Sasaki、Kazuishi Makino、Sylvain Lectard、Yasumasa Hamada

  DOI：10.1016/j.tetlet.2009.02.095

  日期：2009.7

  An organocatalytic enantioselective aziridination reaction of alpha,beta-unsaturated aldehydes including aromatic substrates using N-arenesulfonyloxycarbamates in the presence of diphenylprolinol triethylsilyl ether and sodium carbonate or sodium acetate is described.
• Asymmetric Total Syntheses of (−)-Renieramycin M and G and (−)-Jorumycin Using Aziridine as a Lynchpin
  作者：Yan-Chao Wu、Jieping Zhu

  DOI：10.1021/ol9024919

  日期：2009.12.3

  By exploring the triple reactivity of two aziridines and double nucleophilicity of two aromatics, convergent and versatile syntheses of the above four natural products were developed.