(2S,3R)-1-(t-butoxycarbonyl)-N-(4-methoxyphenyl)-3-(4-methylphenyl)aziridine-2-carboxamide | 1172132-96-5

• 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: (2S,3R)-1-(t-butoxycarbonyl)-N-(4-methoxyphenyl)-3-(4-methylphenyl)aziridine-2-carboxamide
• 英文别名: tert-butyl (2S,3R)-2-[(4-methoxyphenyl)carbamoyl]-3-(4-methylphenyl)aziridine-1-carboxylate
• CAS: 1172132-96-5
• 化学式: C₂₂H₂₆N₂O₄
• 分子量: 382.459
• InChiKey: DAMFPQWMIJYXHT-WEAPTXNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(4-methoxyphenyl)diazoacetamide 、 4-methylbenzaldehyde N-(tert-butoxycarbonyl)imine 在 (S)-3,3'-双(9-蒽基)-1,1'-联萘-2,2'-二基磷酸氢酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (2R,3S)-1-(t-butoxycarbonyl)-N-(4-methoxyphenyl)-3-(4-methylphenyl)aziridine-2-carboxamide 、 (2S,3R)-1-(t-butoxycarbonyl)-N-(4-methoxyphenyl)-3-(4-methylphenyl)aziridine-2-carboxamide
  参考文献：
  名称：

  Highly Efficient Asymmetric Trans-Selective Aziridination of Diazoacetamides and N-Boc-imines Catalyzed by Chiral Brønsted Acids

  摘要：

  A clean and fast (10 min) aziridination of diazoacetamides with N-Boc-imines, as well as N-Cbz-imines, catalyzed by chiral phosphoric acid (R)-5g in DCM at room temperature was developed, The excellent yields (89-97%), diastereoselectivities (trans/cis > 50:1), chemoselectivities (3:4 = >95:5), and enantioselectivities (88-98% ee) were achieved in the reaction.

  DOI：

  10.1021/ol901047w

文献信息

• Highly Efficient Asymmetric <i>Trans-</i>Selective Aziridination of Diazoacetamides and <i>N</i>-Boc-imines Catalyzed by Chiral Brønsted Acids
  作者：Xiaofei Zeng、Xin Zeng、Zhenjiang Xu、Min Lu、Guofu Zhong

  DOI：10.1021/ol901047w

  日期：2009.7.16

  A clean and fast (10 min) aziridination of diazoacetamides with N-Boc-imines, as well as N-Cbz-imines, catalyzed by chiral phosphoric acid (R)-5g in DCM at room temperature was developed, The excellent yields (89-97%), diastereoselectivities (trans/cis > 50:1), chemoselectivities (3:4 = >95:5), and enantioselectivities (88-98% ee) were achieved in the reaction.