3-(4-hydroxyphenyl)-5-propylisoxazole | 1620843-87-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(4-hydroxyphenyl)-5-propylisoxazole
• 英文别名: 4-(5-Propyl-1,2-oxazol-3-yl)phenol；4-(5-propyl-1,2-oxazol-3-yl)phenol
• CAS: 1620843-87-9
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: HOCCAQJMMVVFNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲氧基苯甲醛肟 在 三氟二甲基硫醚络合物 、 chloroamine-T 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.75h， 生成 3-(4-hydroxyphenyl)-5-propylisoxazole
  参考文献：
  名称：

  Microwave-assisted synthesis of 3,5-disubstituted isoxazoles and evaluation of their anti-ageing activity

  摘要：

  One-pot uncatalysed microwave-assisted 1,3-dipolar cycloaddition reactions between in situ generated nitrile oxides and alkynes bearing protected antioxidant substituents, were regioselectively afforded 3,5-disubstituted isoxazoles. The yields were moderate, based on the starting aldehydes, while the reaction times were in general shorter than those reported in the literature. The cytoprotective and anti-ageing effect of the final deprotected compounds was evaluated in vitro, on cellular survival following oxidative challenge and in vivo, on organismal longevity using the nematode Caenorhabditis elegans. The activity of the isoxazole analogues depends on the nature and the number of the antioxidant substituents. Analogue 17 bearing a phenolic group and a 6-OH-chroman group is a promising anti-ageing agent, since it increased survival of human primary fibroblasts following treatment with H2O2 and extended C. elegans lifespan.

  DOI：

  10.1016/j.ejmech.2014.06.046