3-(4-硝基苯基)-5-丙基-1,2,4-噁二唑 | 10364-67-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(4-硝基苯基)-5-丙基-1,2,4-噁二唑
• 中文别名: 3-(4-硝基苯基)-5-丙基-1,2,4-恶二唑
• 英文名称: 5-propyl-3-(4-nitrophenyl)-1,2,4-oxadiazole
• 英文别名: 3-(4-nitro-phenyl)-5-propyl-[1,2,4]oxadiazole；3-p-Nitrophenyl-5-propyl-1,2,4-oxadiazol；3-(4-Nitrophenyl)-5-propyl-1,2,4-oxadiazole
• CAS: 10364-67-7
• 化学式: C₁₁H₁₁N₃O₃
• 分子量: 233.227
• InChiKey: ODAKJMUOVQDEPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  89 °C
• 沸点：
  393.5±44.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-硝基苯基)-5-丙基-1,2,4-噁二唑 在 sodium sulfide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.75h， 以54%的产率得到3-(4'-aminophenyl)-5-propyl-1,2,4-oxadiazole
  参考文献：
  名称：

  Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides

  摘要：

  A number of isosteres (oxadiazoles, thiadiazoles, tetrazoles and diazines) of benzocaine were prepared and evaluated for their capacity to induce methemoglobinemia-with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed within each series, with 1,2,4-oxadiazole 3 (metHb% = 61.0 +/- 3.6) and 1,3,4-oxadiazole 10 (metHb% = 52.4 +/- 0.9) demonstrating the greatest activity. Of the 5 candidates (compounds 3, 10, 11, 13 and 23) evaluated in vivo, failure to induce a lethal end-point at doses of 120 mg/kg was observed in all cases. Inadequate metabolic stability, particularly towards hepatic enzymes such as the CYPs, was postulated as one reason for their failure. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.013
• 作为产物：
  描述：

  对硝基苯甲腈 在 吡啶 、 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 36.5h， 生成 3-(4-硝基苯基)-5-丙基-1,2,4-噁二唑
  参考文献：
  名称：

  Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides

  摘要：

  A number of isosteres (oxadiazoles, thiadiazoles, tetrazoles and diazines) of benzocaine were prepared and evaluated for their capacity to induce methemoglobinemia-with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed within each series, with 1,2,4-oxadiazole 3 (metHb% = 61.0 +/- 3.6) and 1,3,4-oxadiazole 10 (metHb% = 52.4 +/- 0.9) demonstrating the greatest activity. Of the 5 candidates (compounds 3, 10, 11, 13 and 23) evaluated in vivo, failure to induce a lethal end-point at doses of 120 mg/kg was observed in all cases. Inadequate metabolic stability, particularly towards hepatic enzymes such as the CYPs, was postulated as one reason for their failure. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.013