3-<3,5-dimethyl-4-(4-pentyn-1-yloxy)phenyl>-1,2,4-oxadiazole | 156787-39-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-<3,5-dimethyl-4-(4-pentyn-1-yloxy)phenyl>-1,2,4-oxadiazole
• 英文别名: 3-(3,5-Dimethyl-4-pent-4-ynoxyphenyl)-1,2,4-oxadiazole
• CAS: 156787-39-2
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: SSZDJQKNGKDCIL-UHFFFAOYSA-N

物化性质

• 沸点：
  405.5±55.0 °C(predicted)
• 密度：
  1.112±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  propionaldehyde oxime 、 3-<3,5-dimethyl-4-(4-pentyn-1-yloxy)phenyl>-1,2,4-oxadiazole 在 吡啶 、 N-氯代丁二酰亚胺 、 三乙胺 作用下， 生成 3-[4-[3-(3-Ethyl-1,2-oxazol-5-yl)propoxy]-3,5-dimethylphenyl]-1,2,4-oxadiazole
  参考文献：
  名称：

  Oxadiazoles as Ester Bioisosteric Replacements in Compounds Related to Disoxaril. Antirhinovirus Activity

  摘要：

  A series of 1,2,4-oxadiazoles has been prepared as ester bioisosteres and tested against 15 human rhinovirus serotypes, and the MIC(80), the concentration which inhibits 80% or 12 of the serotypes tested, was determined. Homologation of the alkyl group attached to the oxadiazole ring resulted in a reduction in activity with increased chain length. Introduction of hydrophilic groups in this position rendered the compounds inactive. Increasing the length of the side chain attached to the isoxazole ring resulted in an increase in activity. Replacement of the methyl with alkoxyalkyl substituents retained activity; however, introduction of a hydroxyl group on to the side chain reduced activity. Compound 8a, where both the isoxazole and oxadiazole rings were substituted with methyl groups, was one of the most active compounds in the series. A comparison was made between 8a and the two isomeric oxadiazoles 41 and 46, and an attempt was made to explain the difference in activity by examining electrostatic potential maps and by an energy profiling study. No conclusive results were obtained from these studies.

  DOI：

  10.1021/jm00041a022
• 作为产物：
  描述：

  3,5-二甲基-4-羟基苯甲腈 在 三氟化硼乙醚 、 盐酸羟胺 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 为溶剂， 反应 105.75h， 生成 3-<3,5-dimethyl-4-(4-pentyn-1-yloxy)phenyl>-1,2,4-oxadiazole
  参考文献：
  名称：

  Oxadiazoles as Ester Bioisosteric Replacements in Compounds Related to Disoxaril. Antirhinovirus Activity

  摘要：

  A series of 1,2,4-oxadiazoles has been prepared as ester bioisosteres and tested against 15 human rhinovirus serotypes, and the MIC(80), the concentration which inhibits 80% or 12 of the serotypes tested, was determined. Homologation of the alkyl group attached to the oxadiazole ring resulted in a reduction in activity with increased chain length. Introduction of hydrophilic groups in this position rendered the compounds inactive. Increasing the length of the side chain attached to the isoxazole ring resulted in an increase in activity. Replacement of the methyl with alkoxyalkyl substituents retained activity; however, introduction of a hydroxyl group on to the side chain reduced activity. Compound 8a, where both the isoxazole and oxadiazole rings were substituted with methyl groups, was one of the most active compounds in the series. A comparison was made between 8a and the two isomeric oxadiazoles 41 and 46, and an attempt was made to explain the difference in activity by examining electrostatic potential maps and by an energy profiling study. No conclusive results were obtained from these studies.

  DOI：

  10.1021/jm00041a022