1-hydroxy-3-phenylquinolin-2-imine | 59387-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-hydroxy-3-phenylquinolin-2-imine
• 英文别名: 2-amino-3-phenylquinoline 1-oxide；2-Amino-3-phenylchinolin-1-oxid；1-oxy-3-phenyl-quinolin-2-ylamine；1-oxy-3-phenyl-[2]quinolylamine；1-Oxy-3-phenyl-[2]chinolylamin
• CAS: 59387-82-5
• 化学式: C₁₅H₁₂N₂O
• 分子量: 236.273
• InChiKey: PHWXNNRIJWCZAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.96
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-hydroxy-3-phenylquinolin-2-imine 在 二氧化硫 、 水 作用下， 生成 2-氨基-3-苯基喹啉
  参考文献：
  名称：

  Bauer, Chemische Berichte, 1938, vol. 71, p. 2226,2228

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-3-(2-Nitrophenyl)-2-phenylacrylsaeurenitril 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以81%的产率得到1-hydroxy-3-phenylquinolin-2-imine
  参考文献：
  名称：

  Synthese substituierter 2-Aminochinolin-1-oxide durch reduktive Cyclisierung substituierter 3-(2-Nitrophenyl)acrylnitrile

  摘要：

  An approach to the class of 2-aminoquinoline-1-oxides is given based on reductive cyclization of appropriate substituted 3-(2-nitrophenyl)acrylonitriles. Thus, 2-nitrobenzylidene compounds 1a - d have been reductively cyclized by H-2/PtO2 or H-2/Pd-C under normal conditions to form N-oxides 2a - d. H-1-NMR data show that 1d has to be regarded as ethyl(Z)-2-cyano-3-hydroxy-3-(2-nitrophenyl)acrylate.The analogous (2-nitrobenzoyl)acetonitrile 3, however, did not cyclize under the same conditions, but yielded anthraniloylacetonitrile 4. The results are discussed in comparison with the reaction behaviour of structural related nitronitriles under comparable conditions. A short survey of reactions leading to heterocyclic N-oxides by reductive cyclization of nitro compounds is given.

  DOI：

  10.1002/prac.19923340114

文献信息

• Novel and efficient synthesis of substituted quinoline-1-oxides and the complex compounds SnL2Cl2 (L=2-aminoquinoline-1-oxides) with the aid of stannous chloride
  作者：Lei Fu、Wei Lin、Pan Xu、Yu-Kun Xi、Man-Man Wang、Da-Qing Shi

  DOI：10.1016/j.tet.2012.07.049

  日期：2012.9

  A novel and efficient approach to the synthesis of substituted quinoline-1-oxides and the complex compounds SnL2Cl2 (L=2-aminoquinoline-1-oxides) was developed. The reaction has fancy selectivity when 3-(2-nitrophenyl)acrylonitriles were treated with the aid of SnCl2 reagent under the same conditions. When R is -CN or -COOR' the complex compounds SnL2Cl2 (L=2-aminoquinoline-1-oxides) were obtained. Whereas, when R is H or aryl another series of substituted quinoline-1-oxides were formed. The products have been screened for their anticancer activities. (C) 2012 Elsevier Ltd. All rights reserved.
• Bauer, Chemische Berichte, 1938, vol. 71, p. 2226,2228
  作者：Bauer

  DOI：——

  日期：——
• Synthese substituierter 2-Aminochinolin-1-oxide durch reduktive Cyclisierung substituierter 3-(2-Nitrophenyl)acrylnitrile
  作者：D. Sicker、H. Wilde

  DOI：10.1002/prac.19923340114

  日期：——

  An approach to the class of 2-aminoquinoline-1-oxides is given based on reductive cyclization of appropriate substituted 3-(2-nitrophenyl)acrylonitriles. Thus, 2-nitrobenzylidene compounds 1a - d have been reductively cyclized by H-2/PtO2 or H-2/Pd-C under normal conditions to form N-oxides 2a - d. H-1-NMR data show that 1d has to be regarded as ethyl(Z)-2-cyano-3-hydroxy-3-(2-nitrophenyl)acrylate.The analogous (2-nitrobenzoyl)acetonitrile 3, however, did not cyclize under the same conditions, but yielded anthraniloylacetonitrile 4. The results are discussed in comparison with the reaction behaviour of structural related nitronitriles under comparable conditions. A short survey of reactions leading to heterocyclic N-oxides by reductive cyclization of nitro compounds is given.
• KHMDS Mediated Ring-Opening/Reconstruction of Anthranils with Arylacetonitriles: Synthesis of Multisubstituted 2-Aminoquinoline <i>N</i>-Oxides
  作者：Ram Singh Jat、Gautami Singh、M. Bhanuchandra

  DOI：10.1039/d4nj00311j

  日期：——

  A convenient and atom-economical protocol for the construction of multisubstituted 2-aminoquinoline N-oxides using readily available starting materials anthranil and arylacetonitrile has been reported. The KHMDS mediated process tolerates various protecting...