(4-乙酰氨基-3-溴-2-甲基苯基)乙酸甲酯 | 890086-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-乙酰氨基-3-溴-2-甲基苯基)乙酸甲酯
• 英文名称: (4-Acetamido-3-bromo-2-methylphenyl)methyl acetate
• CAS: 890086-37-0
• 化学式: C₁₂H₁₄BrNO₃
• 分子量: 300.152
• InChiKey: FVIFJWGWGXFMIL-UHFFFAOYSA-N

物化性质

• 沸点：
  419.4±45.0 °C(Predicted)
• 密度：
  1.444±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-硝基邻二甲苯 在 甲醇 、 sodium tetrahydroborate 、 1,3-二溴-5,5-二甲基海因 、 三乙胺 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 3.5h， 生成 (4-乙酰氨基-5-溴-2-甲基苯基)乙酸甲酯 、 (4-乙酰氨基-3-溴-2-甲基苯基)乙酸甲酯
  参考文献：
  名称：

  Chemical Development of ZD9331:  Synthesis of a Bromomethylquinazolinone Avoiding a Nonselective Radical Bromination

  摘要：

  An efficient regiospecific synthesis of ZD9331 Pivaloyloxymethyl (POM) Bromide ( 4) has been accomplished via ZD9331 Quinacetate HCl ( 15) avoiding a nonselective bromination. The original route used a radical bromination on a substrate with three methyl groups, which generated a range of bromomethyl derived compounds that carried through to the final active pharmaceutical ingredient (API). A strategy, based on the Zinin reaction, was developed to synthesize the required bromomethyl compound in a regioselective manner. This approach was successfully scaled to manufacture a tonne of material.

  DOI：

  10.1021/op060049a

文献信息

• Chemical Development of ZD9331:  Synthesis of a Bromomethylquinazolinone Avoiding a Nonselective Radical Bromination
  作者：Dagmar Bentley、Andrew A. Godfrey、Kenneth E. H. Warren

  DOI：10.1021/op060049a

  日期：2006.5.1

  An efficient regiospecific synthesis of ZD9331 Pivaloyloxymethyl (POM) Bromide ( 4) has been accomplished via ZD9331 Quinacetate HCl ( 15) avoiding a nonselective bromination. The original route used a radical bromination on a substrate with three methyl groups, which generated a range of bromomethyl derived compounds that carried through to the final active pharmaceutical ingredient (API). A strategy, based on the Zinin reaction, was developed to synthesize the required bromomethyl compound in a regioselective manner. This approach was successfully scaled to manufacture a tonne of material.