4-Chlor-N-(2-methoxy-benzyliden)-anilin-N-oxid | 19865-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-Chlor-N-(2-methoxy-benzyliden)-anilin-N-oxid
• 英文别名: N-(o-Methoxy-benzyliden)-p-chlor-anilin-N-oxid；4-Chlor-N-(2-methoxy-benzyliden)-N-oxy-anilin；N-(4-chlorophenyl)-1-(2-methoxyphenyl)methanimine oxide
• CAS: 19865-62-4
• 化学式: C₁₄H₁₂ClNO₂
• 分子量: 261.708
• InChiKey: YXKKDOOUKQUKBL-UHFFFAOYSA-N

物化性质

• 沸点：
  420.9±55.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-环己基马来酰亚胺 、 4-Chlor-N-(2-methoxy-benzyliden)-anilin-N-oxid 以 甲苯 为溶剂， 以64%的产率得到2-(4'-chlorophenyl)-5-cyclohexyl-3-(2''-methoxyphenyl)-4H-2,3,3a,5,6,6a-hexahydropyrrolo[3,4-d]isoxazole-4,6-dione
  参考文献：
  名称：

  Synthesis and Evaluation of Novel 5-cyclohexyl-2-(4″-substitutedphenyl)-3-(2″-substitutedphenyl)4H-2,3,3a,5,6,6a-hexahydropyrrolo[3,4-d]isoxazole-4,6-dione Derivatives for TheirIn VitroAntioxidant and Antibacterial Activities

  摘要：

  1,3‐Dipolar cycloaddition reactions of N‐cyclohexyl maleimide (1) with azomethine N‐oxide (2) have afforded novel isoxazolidine (3) in excellent yield. Their structures have been characterized from their IR, 1H‐NMR, 13C‐NMR, 1H,1H‐COSY, MS(ESI), and elemental analysis techniques. In vitro antibacterial activity of the synthesized compounds were investigated against a representative panel of pathogenic strains specifically two Gram‐positive bacteria (Staphylococcus aureus and Streptococcus pyogenes) and two Gram‐negative bacteria (Pseudomonas aeruginosa and Escherichia coli) using agar‐well diffusion assay. Some of the compounds (3a, 3k, 3n, and 3o) exhibited promising antibacterial activities. All the synthesized compounds have also been screened for their antioxidant activities and were found to be significantly active.

  DOI：

  10.1002/jhet.2543
• 作为产物：
  描述：

  对硝基氯苯 在 氯化铵 、 锌 作用下， 以 氯仿 、 水 为溶剂， 反应 1.25h， 生成 4-Chlor-N-(2-methoxy-benzyliden)-anilin-N-oxid
  参考文献：
  名称：

  Synthesis and Evaluation of Novel 5-cyclohexyl-2-(4″-substitutedphenyl)-3-(2″-substitutedphenyl)4H-2,3,3a,5,6,6a-hexahydropyrrolo[3,4-d]isoxazole-4,6-dione Derivatives for TheirIn VitroAntioxidant and Antibacterial Activities

  摘要：

  1,3‐Dipolar cycloaddition reactions of N‐cyclohexyl maleimide (1) with azomethine N‐oxide (2) have afforded novel isoxazolidine (3) in excellent yield. Their structures have been characterized from their IR, 1H‐NMR, 13C‐NMR, 1H,1H‐COSY, MS(ESI), and elemental analysis techniques. In vitro antibacterial activity of the synthesized compounds were investigated against a representative panel of pathogenic strains specifically two Gram‐positive bacteria (Staphylococcus aureus and Streptococcus pyogenes) and two Gram‐negative bacteria (Pseudomonas aeruginosa and Escherichia coli) using agar‐well diffusion assay. Some of the compounds (3a, 3k, 3n, and 3o) exhibited promising antibacterial activities. All the synthesized compounds have also been screened for their antioxidant activities and were found to be significantly active.

  DOI：

  10.1002/jhet.2543

文献信息

• 1,3-dipolar cycloaddition reactions of 2-substituted azomethine N-oxides with N-benzyl maleimides leading to the synthesis of stereoisomers
  作者：Rahul Badru、Sakshi Shah、Baldev Singh

  DOI：10.1002/jhet.794

  日期：2012.3

  The azomethine N‐oxides (1) on reacting with N‐benzylmaleimide (2) provide a mixture of stereoisomers 2,3‐diphenyl‐5‐benzyl‐4H‐2,3,3a,5,6,6a‐hexahydropyrrolo[3,4‐d]isoxazole‐4,6–dione derivatives (3) in good yields. These isomers have been assigned cis and trans configurations (3‐A and 3‐B) with respect to proton C3‐H on the azomethinic carbon on the basis of their PMR and H‐NMR COSY data. The ratio

  与N-苄基马来酰亚胺（2）反应时，偶氮甲碱N-氧化物（1）提供了立体异构体2,3-二苯基-5-苄基4 H -2,3,3a，5,6,6a-六氢吡咯[3]的混合物，4 - d ]异恶唑-4,6-二酮衍生物（3），收率高。根据其PMR和H-NMR COZY数据，已将这些异构体相对于偶氮二甲基碳上的质子C 3 -H分配了顺式和反式构型（3-A和3-B）。发现顺式和反式异构体之间的比例取决于存在于C的邻位的取代基-苯基醛基部分。这些1,3-偶极环加成反应的显着特征在于，N-苄基部分上的苄基质子遭受宝石耦合，表明磁性不等价。J.杂环化​​学。，（2012）。
• Synthesis and Evaluation of Novel 5-cyclohexyl-2-(4″-substitutedphenyl)-3-(2″-substitutedphenyl)4<i>H</i>-2,3,3a,5,6,6a-hexahydropyrrolo[3,4-<i>d</i>]isoxazole-4,6-dione Derivatives for Their<i>In Vitro</i>Antioxidant and Antibacterial Activities
  作者：Manpreet Kaur、Anjandeep Kaur、Baldev Singh、Baljit Singh

  DOI：10.1002/jhet.2543

  日期：2017.1

  1,3‐Dipolar cycloaddition reactions of N‐cyclohexyl maleimide (1) with azomethine N‐oxide (2) have afforded novel isoxazolidine (3) in excellent yield. Their structures have been characterized from their IR, 1H‐NMR, 13C‐NMR, 1H,1H‐COSY, MS(ESI), and elemental analysis techniques. In vitro antibacterial activity of the synthesized compounds were investigated against a representative panel of pathogenic strains specifically two Gram‐positive bacteria (Staphylococcus aureus and Streptococcus pyogenes) and two Gram‐negative bacteria (Pseudomonas aeruginosa and Escherichia coli) using agar‐well diffusion assay. Some of the compounds (3a, 3k, 3n, and 3o) exhibited promising antibacterial activities. All the synthesized compounds have also been screened for their antioxidant activities and were found to be significantly active.