N-benzoyl-3-bromo-2,6-dimethyl-1,4-benzoquinone monoimine | 924831-13-0

• 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: N-benzoyl-3-bromo-2,6-dimethyl-1,4-benzoquinone monoimine
• 英文别名: N-(2-bromo-3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)benzamide
• CAS: 924831-13-0
• 化学式: C₁₅H₁₂BrNO₂
• 分子量: 318.17
• InChiKey: YVBXUTXFTLZGCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzoyl-3-bromo-2,6-dimethyl-1,4-benzoquinone monoimine 在 溴 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-benzoyloxy-3,6-dibromo-2,6-dimethylcyclohex-2-ene-1,4-dione
  参考文献：
  名称：

  Halogenation of N-substituted para-quinone monoimines and para-quinone monoximes ethers: IX. Halogenation of N-aroyl-2,6(3,5)-dimethyl-1,4-benzoquinone monoimines and their reduced forms

  摘要：

  At the halogenation of N-aroyl-2,6(3,5)-dimethyl-1,4-benzoquinone imines we found the halogenation of methyl groups to occur. The bromination of N-aroyl-2,6-dimethyl-1,4-benzoquinone imines yielded 3,6-dibromo2,6-dimethyl-5-aroyloxycyclohex-2-ene-1,4-diones due to the strong acceptor property of the ArCO group and high redox potentials of N-aroyl derivatives. In the chlorination of N-aroyl-3,5-dimethyl-1,4-benzoquinone imines the chlorine addition to the C=C bond of the quinoid ring proceeded both by the trans-and syn-scheme.

  DOI：

  10.1134/s1070428009110128
• 作为产物：
  描述：

  N-(3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)benzamide 在 溴 作用下， 以 溶剂黄146 为溶剂， 生成 N-benzoyl-3-bromo-2,6-dimethyl-1,4-benzoquinone monoimine
  参考文献：
  名称：

  Halogenation of N-substituted para-quinone monoimines and para-quinone monoximes ethers: IX. Halogenation of N-aroyl-2,6(3,5)-dimethyl-1,4-benzoquinone monoimines and their reduced forms

  摘要：

  At the halogenation of N-aroyl-2,6(3,5)-dimethyl-1,4-benzoquinone imines we found the halogenation of methyl groups to occur. The bromination of N-aroyl-2,6-dimethyl-1,4-benzoquinone imines yielded 3,6-dibromo2,6-dimethyl-5-aroyloxycyclohex-2-ene-1,4-diones due to the strong acceptor property of the ArCO group and high redox potentials of N-aroyl derivatives. In the chlorination of N-aroyl-3,5-dimethyl-1,4-benzoquinone imines the chlorine addition to the C=C bond of the quinoid ring proceeded both by the trans-and syn-scheme.

  DOI：

  10.1134/s1070428009110128

文献信息

• Halogenation of N-substituted para-quinone monoimines and para-quinone monoximes ethers: IX. Halogenation of N-aroyl-2,6(3,5)-dimethyl-1,4-benzoquinone monoimines and their reduced forms
  作者：A. P. Avdeenko、S. A. Konovalova、O. N. Ludchenko、G. V. Palamarchuk、O. V. Shishkin

  DOI：10.1134/s1070428009110128

  日期：2009.11

  At the halogenation of N-aroyl-2,6(3,5)-dimethyl-1,4-benzoquinone imines we found the halogenation of methyl groups to occur. The bromination of N-aroyl-2,6-dimethyl-1,4-benzoquinone imines yielded 3,6-dibromo2,6-dimethyl-5-aroyloxycyclohex-2-ene-1,4-diones due to the strong acceptor property of the ArCO group and high redox potentials of N-aroyl derivatives. In the chlorination of N-aroyl-3,5-dimethyl-1,4-benzoquinone imines the chlorine addition to the C=C bond of the quinoid ring proceeded both by the trans-and syn-scheme.