(E)-2-((1-hydroxy-2-methylpropan-2-ylimino)methyl)-4-nitrophenol | 1350842-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-2-((1-hydroxy-2-methylpropan-2-ylimino)methyl)-4-nitrophenol
• CAS: 1350842-45-3
• 化学式: C₁₁H₁₄N₂O₄
• 分子量: 238.243
• InChiKey: LFUQGVMMWIATOD-WUXMJOGZSA-N

物化性质

• 沸点：
  412.8±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  95.96
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-氨基-2-甲基-1-丙醇 、 5-硝基水杨醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以95%的产率得到(E)-2-((1-hydroxy-2-methylpropan-2-ylimino)methyl)-4-nitrophenol
  参考文献：
  名称：

  Racemization of secondary alcohols catalyzed by ruthenium: application to chemoenzymatic dynamic resolution

  摘要：

  In this paper, we have shown that the [RuCl2(p-cymene)](2) complex associated with simple hemisalen ligands is able to racemize (S)-1-phenylethanol. The influence on the racemization process of the ligand's structure as well as the nature of a co-catalyst have been evaluated and optimized. This [RuCl2(p-cymene)](2)/Ligand/TEMPO racemization system was then associated with the Candida Antarctica B lipase in order to carry out dynamic kinetic resolution experiments on rac-phenylethanol. This led us to identify the best conditions for effective DKR, which was then applied to various secondary benzylic and aliphatic alcohols. It was thus possible to obtain (R)-1-cyclohexylethyl acetate from rac-1-cyclohexylethanol in quantitative conversion and with high enantioselectivity (98%). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.007
• 作为试剂：
  描述：

  乙酸异丙烯酯 、 苏合香醇 在 2,2,6,6-四甲基哌啶氧化物 、 Candida antarctica B lipase 、 二氯(p-甲基异丙苯)钌(II) 二聚体 、 (E)-2-((1-hydroxy-2-methylpropan-2-ylimino)methyl)-4-nitrophenol 作用下， 以 甲苯 为溶剂， 反应 72.0h， 生成 (S)-1-phenylethyl acetate 、 (R)-1-phenethyl acetate 、 苯乙酮
  参考文献：
  名称：

  Racemization of secondary alcohols catalyzed by ruthenium: application to chemoenzymatic dynamic resolution

  摘要：

  In this paper, we have shown that the [RuCl2(p-cymene)](2) complex associated with simple hemisalen ligands is able to racemize (S)-1-phenylethanol. The influence on the racemization process of the ligand's structure as well as the nature of a co-catalyst have been evaluated and optimized. This [RuCl2(p-cymene)](2)/Ligand/TEMPO racemization system was then associated with the Candida Antarctica B lipase in order to carry out dynamic kinetic resolution experiments on rac-phenylethanol. This led us to identify the best conditions for effective DKR, which was then applied to various secondary benzylic and aliphatic alcohols. It was thus possible to obtain (R)-1-cyclohexylethyl acetate from rac-1-cyclohexylethanol in quantitative conversion and with high enantioselectivity (98%). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.007