N-Benzoyl-2-hydroxy-5-aminobiphenyl | 66723-72-6

• 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-2-hydroxy-5-aminobiphenyl
• 英文别名: N-(4-hydroxy-3-phenylphenyl)benzamide
• CAS: 66723-72-6
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: ARXLUCOYLMFPPA-UHFFFAOYSA-N

物化性质

• 沸点：
  401.9±38.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  N-Benzoyl-2-hydroxy-5-aminobiphenyl 以95%的产率得到
  参考文献：
  名称：

  Novak Michael, Helmick John S., Oberlies Nicholas, Rangappa Kanchugarakop+, J. Org. Chem, 53 (1993) N 4, S 867-878

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基-2-苯基苯酚 在 platinum on activated charcoal 氢气 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 25.0 ℃ 、448.16 kPa 条件下， 反应 3.25h， 生成 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

文献信息

• 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
  作者：Michael Novak、John S. Helmick、Nicholas Oberlies、Kanchugarakoppal S. Rangappa、William M. Clark、John S. Swenton

  DOI：10.1021/jo00056a019

  日期：1993.2

  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.
• Novak Michael, Helmick John S., Oberlies Nicholas, Rangappa Kanchugarakop+, J. Org. Chem, 53 (1993) N 4, S 867-878
  作者：Novak Michael, Helmick John S., Oberlies Nicholas, Rangappa Kanchugarakop+

  DOI：——

  日期：——