N-(4-acetylphenyl)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)acetamide | 905514-05-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-acetylphenyl)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)acetamide
• 英文别名: N-(4-acetylphenyl)-2-[[5-(3-nitrophenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide
• CAS: 905514-05-8
• 化学式: C₁₈H₁₄N₄O₅S
• 分子量: 398.399
• InChiKey: BBGBZYSSWSJEJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(4-acetylphenyl)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)acetamide 、 苯甲醛 在 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以62%的产率得到(Z)-N-(4-cinnamoylphenyl)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)acetamide
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of 1,3,4-oxadiazole-based chalcone derivatives

  摘要：

  A series of chalcones-bearing 1,3,4-oxadiazole derivatives was synthesized as novel bio-active antimicrobial agents against multidrug-resistant bacteria and fungi. The lead compounds (Z)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)-N-(4-(3-(aryl)acryloyl)phenyl)acetamides 5a-n were synthesized via acid-catalyzed aldol condensation (SOCl2) by reacting N-(4-acetylphenyl)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)acetamide (4) with differently substituted aldehydes. Compound (4) was obtained by reacting 5-(3-nitrophenyl)-1,3,4-oxadiazole-2-thiol (2) with N-(4-acetylphenyl)-2-chloroacetamide (3) in the presence of K2CO3. The intermediates (2) and (3) were synthesized simultaneously from 3-nitrobenzohydrazide (1) and 4-aminoacetophenone, respectively. The formation of intermediates and targeted compounds were confirmed for their structure by means of various spectral-analytical techniques like IR, H-1 NMR, C-13 NMR, elemental analysis, and mass spectra. Antimicrobial properties of all the synthesized compounds have been evaluated against broad panel of bacteria and fungi.

  DOI：

  10.1007/s00044-013-0791-1
• 作为产物：
  描述：

  3-硝基苯酰肼 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 N-(4-acetylphenyl)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)acetamide
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of 1,3,4-oxadiazole-based chalcone derivatives

  摘要：

  A series of chalcones-bearing 1,3,4-oxadiazole derivatives was synthesized as novel bio-active antimicrobial agents against multidrug-resistant bacteria and fungi. The lead compounds (Z)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)-N-(4-(3-(aryl)acryloyl)phenyl)acetamides 5a-n were synthesized via acid-catalyzed aldol condensation (SOCl2) by reacting N-(4-acetylphenyl)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)acetamide (4) with differently substituted aldehydes. Compound (4) was obtained by reacting 5-(3-nitrophenyl)-1,3,4-oxadiazole-2-thiol (2) with N-(4-acetylphenyl)-2-chloroacetamide (3) in the presence of K2CO3. The intermediates (2) and (3) were synthesized simultaneously from 3-nitrobenzohydrazide (1) and 4-aminoacetophenone, respectively. The formation of intermediates and targeted compounds were confirmed for their structure by means of various spectral-analytical techniques like IR, H-1 NMR, C-13 NMR, elemental analysis, and mass spectra. Antimicrobial properties of all the synthesized compounds have been evaluated against broad panel of bacteria and fungi.

  DOI：

  10.1007/s00044-013-0791-1