4-amino-N-benzoyl-3,5-dimethylphenol | 68395-69-7

• 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: 4-amino-N-benzoyl-3,5-dimethylphenol
• 英文别名: N-(4-hydroxy-2,6-dimethylphenyl)benzamide
• CAS: 68395-69-7
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: RXCARBQIXKLBTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-amino-N-benzoyl-3,5-dimethylphenol 在 lead(IV) tetraacetate 、 溶剂黄146 作用下， 生成 N-(1-methoxy-2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-yl)benzamide
  参考文献：
  名称：

  Activated sterically strained C=N bond in N-substituted p-quinone mono- and diimines: XIV. Reaction of some 3,5-dimethyl-1,4-benzoquinone monoimines with alcohols

  摘要：

  Steric strain in the C=N-C fragment in 3,5-disubstituted N-acyl-1,4-benzoquinone monoimines, unlike their N-arylsulfonyl analogs, leads to increase of the C=N-C angle above 130A degrees or twisting of the double C=N bond and loss of planarity of the quinoid ring. This structural transformation enhances the reactivity of the C=N bond so that 1,2-addition of alcohols becomes possible with formation of sterically unstrained cyclohexadienone structure with sp (3)-hybridized C-4 carbon atom. DOI: 10.1134/S1070428013010107

  DOI：

  10.1134/s1070428013010107
• 作为产物：
  描述：

  3,5-二甲基-4-氨基苯酚 、 苯甲酸酐 以93%的产率得到4-amino-N-benzoyl-3,5-dimethylphenol
  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