2-bromo-3,6-dimethoxy-4-methyl-p-benzoquinone | 383179-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-3,6-dimethoxy-4-methyl-p-benzoquinone
• 英文别名: 2-Bromo-3,6-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione
• CAS: 383179-82-6
• 化学式: C₉H₉BrO₄
• 分子量: 261.072
• InChiKey: ATDYRWHYZOVVSM-UHFFFAOYSA-N

物化性质

• 沸点：
  351.4±42.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-bromo-3,6-dimethoxy-4-methyl-p-benzoquinone 、 1-(1-phenylethyl)-2-(tributylstannylmethylene)pirrolidine 以 四氢呋喃 为溶剂， 反应 0.5h， 以40%的产率得到2-Bromo-6-methoxy-5-methyl-3-[1-(1-phenyl-ethyl)-pyrrolidin-(2E)-ylidenemethyl]-[1,4]benzoquinone
  参考文献：
  名称：

  Use of the Vicinal Element Effect for Regiochemical Control of Quinone Substitutions and Its Implication for Convergent Mitomycin Construction

  摘要：

  [GRAPHICS]Nucleophilic substitution reactions of 2-methoxy-3-alkyl-p-benzoquinones are described as they relate to the construction of the mitomycin backbone. Normally controlled by activating groups attached to the olefin, the observed regioselection in these cases is determined by the deactivating substituent. Approximation of carbonyl activating ability would not have predicted the behavior of two systems investigated in which the poorer of two leaving groups is substituted in each case.

  DOI：

  10.1021/ol016625z
• 作为产物：
  描述：

  2,3-Dibromo-5-methoxy-6-methyl-1,4-benzoquinone 、 magnesium methanolate 以 甲醇 为溶剂， 反应 2.0h， 以55%的产率得到2-bromo-3,6-dimethoxy-4-methyl-p-benzoquinone
  参考文献：
  名称：

  Use of the Vicinal Element Effect for Regiochemical Control of Quinone Substitutions and Its Implication for Convergent Mitomycin Construction

  摘要：

  [GRAPHICS]Nucleophilic substitution reactions of 2-methoxy-3-alkyl-p-benzoquinones are described as they relate to the construction of the mitomycin backbone. Normally controlled by activating groups attached to the olefin, the observed regioselection in these cases is determined by the deactivating substituent. Approximation of carbonyl activating ability would not have predicted the behavior of two systems investigated in which the poorer of two leaving groups is substituted in each case.

  DOI：

  10.1021/ol016625z