1-butanoyloxy-2-bromo-1-(4-nitrophenyl)ethane | 849359-49-5

• 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: 1-butanoyloxy-2-bromo-1-(4-nitrophenyl)ethane
• 英文别名: [2-Bromo-1-(4-nitrophenyl)ethyl] butanoate
• CAS: 849359-49-5
• 化学式: C₁₂H₁₄BrNO₄
• 分子量: 316.151
• InChiKey: YEIPKEWDMBEKCK-UHFFFAOYSA-N

物化性质

• 沸点：
  394.4±32.0 °C(Predicted)
• 密度：
  1.453±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-butanoyloxy-2-bromo-1-(4-nitrophenyl)ethane 在 sodium hydroxide 、 sodium phosphate buffer 、 磷脂酶B 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 2.0h， 生成 (R)-1-butanoyloxy-2-bromo-1-(4-nitrophenyl)ethane 、 (S)-1-butanoyloxy-2-bromo-1-(4-nitrophenyl)ethane 、 (S)-(+)-2-bromo-1-(4-nitrophenyl)ethanol 、 (R)-(-)-2-溴-1-(对硝基苯基)乙醇
  参考文献：
  名称：

  Synthesis of β-adrenergic blockers (R)-(−)-nifenalol and (S)-(+)-sotalol via a highly efficient resolution of a bromohydrin precursor

  摘要：

  (R)- and (S)-2-bromo-1-(4-nitrophenyl)ethanol are precursors of important P-adrenergic receptor blocking drugs (R)-nifenalol and (S)-sotalol, respectively. Both were obtained in enantiomeric pure forms via a single highly efficient enzymatic transesterification reaction of (+/-)-2-bromo-1-(4-nitrophenyl)ethanol using immobilized lipase PS-C-II (E > 1000; concn 200 g/L), while PS lipase completely failed to react. On the other hand, the hydrolytic method also produced enantiorich precursors though relatively less efficient (PS-C-II, E = 5.1). Out of all the approaches employed the transesterification method proved to be the most efficient. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.12.016
• 作为产物：
  描述：

  2-溴-4'-硝基苯乙酮 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-butanoyloxy-2-bromo-1-(4-nitrophenyl)ethane
  参考文献：
  名称：

  Synthesis of β-adrenergic blockers (R)-(−)-nifenalol and (S)-(+)-sotalol via a highly efficient resolution of a bromohydrin precursor

  摘要：

  (R)- and (S)-2-bromo-1-(4-nitrophenyl)ethanol are precursors of important P-adrenergic receptor blocking drugs (R)-nifenalol and (S)-sotalol, respectively. Both were obtained in enantiomeric pure forms via a single highly efficient enzymatic transesterification reaction of (+/-)-2-bromo-1-(4-nitrophenyl)ethanol using immobilized lipase PS-C-II (E > 1000; concn 200 g/L), while PS lipase completely failed to react. On the other hand, the hydrolytic method also produced enantiorich precursors though relatively less efficient (PS-C-II, E = 5.1). Out of all the approaches employed the transesterification method proved to be the most efficient. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.12.016