(2R,5S)-2-((S)-aziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (2R,5S)-2-((S)-aziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol
• 英文别名: (2R,5S)-2-[(2S)-aziridin-2-yl]-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol
• 化学式: C₆H₁₀N₂O₂
• 分子量: 142.158
• InChiKey: WLKQLTSLRNRVSR-RWPYEQMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  反式肉桂醛 、 (2R,5S)-2-((S)-aziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol 在 四氢吡咯 、 苯甲酸 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以86%的产率得到(E)-2-((S)-((S)-aziridin-2-yl)(hydroxy)methyl)-3-phenylacrylaldehyde
  参考文献：
  名称：

  Amphoteric Amino Aldehydes Reroute the Aza-Michael Reaction

  摘要：

  Amphoteric amino aldehydes, which exist as stable dimers, participate in an aza-Michael/aldol domino reaction with alpha,beta-unsaturated aldehydes to afford stable 1,5-aminohydroxyaldehydes in high yields and diastereoselectivies. The reaction outcome hinges upon the dimeric nature of amphoteric amino aldehydes and the orthogonality between the NH aziridine and the two aldehyde functionalities during the reaction. Through the use of reaction conditions that disfavor dimer dissociation, the aza-Michael process has been directed toward a novel 8-(enolendo)-exo-trig cyclization. The results described herein further demonstrate the potential of amphoteric molecules in reaction discovery.

  DOI：

  10.1021/ja9072194
• 作为产物：
  描述：

  (S)-butyl azidirine-2-carboxylate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以76%的产率得到(2R,5S)-2-((S)-aziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol
  参考文献：
  名称：

  Amphoteric Amino Aldehydes Reroute the Aza-Michael Reaction

  摘要：

  Amphoteric amino aldehydes, which exist as stable dimers, participate in an aza-Michael/aldol domino reaction with alpha,beta-unsaturated aldehydes to afford stable 1,5-aminohydroxyaldehydes in high yields and diastereoselectivies. The reaction outcome hinges upon the dimeric nature of amphoteric amino aldehydes and the orthogonality between the NH aziridine and the two aldehyde functionalities during the reaction. Through the use of reaction conditions that disfavor dimer dissociation, the aza-Michael process has been directed toward a novel 8-(enolendo)-exo-trig cyclization. The results described herein further demonstrate the potential of amphoteric molecules in reaction discovery.

  DOI：

  10.1021/ja9072194

文献信息

• Amphoteric Amino Aldehydes Reroute the Aza-Michael Reaction
  作者：Ryan Hili、Andrei K. Yudin

  DOI：10.1021/ja9072194

  日期：2009.11.18

  Amphoteric amino aldehydes, which exist as stable dimers, participate in an aza-Michael/aldol domino reaction with alpha,beta-unsaturated aldehydes to afford stable 1,5-aminohydroxyaldehydes in high yields and diastereoselectivies. The reaction outcome hinges upon the dimeric nature of amphoteric amino aldehydes and the orthogonality between the NH aziridine and the two aldehyde functionalities during the reaction. Through the use of reaction conditions that disfavor dimer dissociation, the aza-Michael process has been directed toward a novel 8-(enolendo)-exo-trig cyclization. The results described herein further demonstrate the potential of amphoteric molecules in reaction discovery.