N-Benzoyl-4-hydroxy-4-phenyl-p-benzoquinol imine | 146474-22-8

• 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-4-hydroxy-4-phenyl-p-benzoquinol imine
• 英文别名: 4-Phenyl-p-benzoquinol N-benzoylimine
• CAS: 146474-22-8
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: AOEPQABCTOVABI-JZJYNLBNSA-N

物化性质

• 沸点：
  491.5±55.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  49.66
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-Benzoyl-4-hydroxy-4-phenyl-p-benzoquinol imine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到N-Benzoyl-2-hydroxy-5-aminobiphenyl
  参考文献：
  名称：

  The electrochemical preparation and kinetic and product studies of acylated quinol and quinol ether imines. In search of the hydrolysis products of the ultimate carcinogen of N-acetyl-2-aminofluorene

  摘要：

  The N-acetyl and benzoyl derivatives of 4-methoxy-4-phenyl-2,5-cyclohexadienone imine and the N-benzoyl derivative of 4-hydroxy-4-phenyl-2,5-cyclohexadienone imine (1a-c) have been prepared via anodic oxidation of the corresponding amide of 4-aminobiphenyl in either methanol or water/acetonitrile, respectively. The products and the kinetics of the acidic and basic hydrolyses of these compounds were studied and the results compared with other N-acylquinol imine derivatives, including N-acetyl-4-hydroxy-4-phenyl-2,5-cyclohexadienone imine (1d), generated by solvolytic routes. The chemistry of these compounds was dependent upon the pH and the substituents on the quinol imine derivative. The major reaction pathways were hydrolysis of the imine linkage to afford the respective dienone and phenyl migration to afford the amides of 2-hydroxy- or 2-methoxy-5-aminobiphenyl. The reactivity of the quinol imine derivatives follows the order: 4-hydroxyl more reactive than 4-methoxyl compounds and N-acetyl more reactive than N-benzoyl derivatives. The higher reactivity for the former compounds is attributed to the greater electron-donating ability of the 4-hydroxyl versus the 4-methoxyl group. The higher reactivity of the N-acetyl relative to the N-benzoyl derivatives is attributed to the ca. 30-fold increase in basicity of the N-acetyl functionality. The additive effect of the 4-hydroxyl and N-acetyl functionality on the basic quinol imine moiety makes compounds having both of the groups difficult to isolate in aqueous media. This serves as a limitation for the preparation of the quinol imine derivative of N-acetyl-2-aminofluorene via the anodic oxidation methods reported herein.

  DOI：

  10.1021/jo00056a019
• 作为产物：
  描述：

  N-4-联苯基苯甲酰胺 在 水 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以53%的产率得到N-Benzoyl-4-hydroxy-4-phenyl-p-benzoquinol imine
  参考文献：
  名称：

  Preparation of quinol N-acyl- and quinol ether imines via anodic oxidation of para-substituted anilide derivatives

  摘要：

  Anodic oxidation of N-benzoyl-4-methylaniline in 5 % aqueous methanol in the presence of sodium bicarbonate affords two major products: 4-methoxy-4-methylbenzoquinol N-benzoylimine, 8a, and a dimer, 4-[N-benzoyl-N-(4-methylphenyl)amino]-4-methylbenzoquinol N-benzoylimine, 9. The ratio of these two products was temperature dependent, and conditions were developed for preparing 8a and 9 in good yield. Using the conditions developed for 8a, the anodic methoxylation of N-benzoyl and acetyl derivatives of 4-ethyl- and 4-sec-butyl-4-phenylaniline and 2-aminofluorene derivatives was performed. The yields of the N-benzoyl derivatives of the 4-methoxy-4-substituted-benzoquinol imines were 46-80%, while the N-acetyl derivatives gave lower yields. When the anodic oxidation was performed using 30% water/acetonitrile or 10 % water/tetrahydrofuran, the 4-alkylbenzoquinol N-benzoylimine derivatives were obtained. The yields of these anodic hydroxylation reactions were lower than those of the corresponding methoxylations for all systems studied. In addition, the 4-alkylbenzoquinol N-benzoylimine derivatives were much more labile. Two methods were developed for conversion of the 4-methoxy-4-substituted-benzoquinol N-acylimines to the 4-methoxy-4-substituted-benzoquinol N-alkylimines. Finally, the especially labile 4-hydroxy-4-phenylbenzoquinol N-acetylimine was prepared for the first time from the readily available N-benzoyl derivative.

  DOI：

  10.1021/jo00073a016