ethyl (2S,3S)-1-[bis(3,5-ditert-butyl-4-methoxyphenyl)methyl]-3-(4-bromophenyl)aziridine-2-carboxylate | 1072879-82-3

• 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: ethyl (2S,3S)-1-[bis(3,5-ditert-butyl-4-methoxyphenyl)methyl]-3-(4-bromophenyl)aziridine-2-carboxylate
• CAS: 1072879-82-3
• 化学式: C₄₂H₅₈BrNO₄
• 分子量: 720.831
• InChiKey: HGOHWJZXQKRGCS-CIKQOIAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  重氮乙酸乙酯 、 N-(4-bromobenzylidene)-bis(4-methoxy-3,5-di-tert-butylphenyl)methylamine 在 C₃₈H₅₂BrNO₂*C₅₂H₃₄B₃O₇^(1-)*H⁽¹⁺⁾ 作用下， 以 tolune-d8 为溶剂， 反应 2.0h， 以715 mg的产率得到ethyl (2S,3S)-1-[bis(3,5-ditert-butyl-4-methoxyphenyl)methyl]-3-(4-bromophenyl)aziridine-2-carboxylate
  参考文献：
  名称：

  Evidence for a Boroxinate Based Brønsted Acid Derivative of VAPOL as the Active Catalyst in the Catalytic Asymmetric Aziridination Reaction

  摘要：

  Studies are described that were designed to determine the structure of the active catalyst in the asymmetric catalytic aziridination of imines with ethyl diazoacetate (AZ reaction). Evidence suggests that the active catalyst contains a boroxine ring in which one of the three boron atoms is spiro-fused with the two phenol groups of the VAPOL tigand. B-11 and H-1 NMR evidence supports the boroxinate structure B in which the counterion to the boroxinate is the protonated form of the imine. The boroxinate structure is also supported by two solid state structures of a VAPOL boroxinate in which the gegen cation is tetramethyl ammonium and 4-dimethylaminopyridinium.

  DOI：

  10.1021/ja904589k

文献信息

• Evidence for a Boroxinate Based Brønsted Acid Derivative of VAPOL as the Active Catalyst in the Catalytic Asymmetric Aziridination Reaction
  作者：Gang Hu、Li Huang、Rui H. Huang、William D. Wulff

  DOI：10.1021/ja904589k

  日期：2009.11.4

  Studies are described that were designed to determine the structure of the active catalyst in the asymmetric catalytic aziridination of imines with ethyl diazoacetate (AZ reaction). Evidence suggests that the active catalyst contains a boroxine ring in which one of the three boron atoms is spiro-fused with the two phenol groups of the VAPOL tigand. B-11 and H-1 NMR evidence supports the boroxinate structure B in which the counterion to the boroxinate is the protonated form of the imine. The boroxinate structure is also supported by two solid state structures of a VAPOL boroxinate in which the gegen cation is tetramethyl ammonium and 4-dimethylaminopyridinium.