3-(4-{2-[4-(2-ethoxycarbonyl-1-methylvinyl)phenoxy]ethoxy}phenyl)but-2-enoic acid ethyl ester | 1092501-42-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(4-{2-[4-(2-ethoxycarbonyl-1-methylvinyl)phenoxy]ethoxy}phenyl)but-2-enoic acid ethyl ester
• CAS: 1092501-42-2
• 化学式: C₂₆H₃₀O₆
• 分子量: 438.521
• InChiKey: CIYHBLBGKVSOQN-UHFFFAOYSA-N

物化性质

• 熔点：
  115-117 °C
• 沸点：
  578.2±38.0 °C(predicted)
• 密度：
  1.115±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-(4-{2-[4-(2-ethoxycarbonyl-1-methylvinyl)phenoxy]ethoxy}phenyl)but-2-enoic acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到3-(4-{2-[4-(3-hydroxy-1-methylpropenyl)phenoxy]ethoxy}phenyl)but-2-en-1-ol
  参考文献：
  名称：

  Novel Bis- and Tris-1,2,4-trioxanes: Synthesis and Antimalarial Activity against Multidrug-Resistant Plasmodium yoelii in Swiss Mice

  摘要：

  A new series of bis-1,2,4-trioxanes 12a-h, 13a-h, and 14a-h and tris-1,2,4-trioxanes 12i-14i were prepared and evaluated against multidrug-resistant Plasmodium yoelii in Swiss mice by oral route. Cyclopentane-based bis-trioxanes 12a, 12b, 12f-h and cyclohexane-based bis-trioxanes 13a, 13f, and 13g showed promising activity. All the tris-1,2,4-trioxanes were found to be inactive. Bis-trioxane 12a, the most active compound of the series, provided 100% and 80% protection to infected mice at 48 and 24 mg/kg x 4 days, respectively. Clinically useful drug P-arteether provided 100% and 20% protection at similar doses.

  DOI：

  10.1021/jm801006v
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 1,2-bis[4-oxyacetophenone]ethane 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以46%的产率得到3-(4-{2-[4-(2-ethoxycarbonyl-1-methylvinyl)phenoxy]ethoxy}phenyl)but-2-enoic acid ethyl ester
  参考文献：
  名称：

  Novel Bis- and Tris-1,2,4-trioxanes: Synthesis and Antimalarial Activity against Multidrug-Resistant Plasmodium yoelii in Swiss Mice

  摘要：

  A new series of bis-1,2,4-trioxanes 12a-h, 13a-h, and 14a-h and tris-1,2,4-trioxanes 12i-14i were prepared and evaluated against multidrug-resistant Plasmodium yoelii in Swiss mice by oral route. Cyclopentane-based bis-trioxanes 12a, 12b, 12f-h and cyclohexane-based bis-trioxanes 13a, 13f, and 13g showed promising activity. All the tris-1,2,4-trioxanes were found to be inactive. Bis-trioxane 12a, the most active compound of the series, provided 100% and 80% protection to infected mice at 48 and 24 mg/kg x 4 days, respectively. Clinically useful drug P-arteether provided 100% and 20% protection at similar doses.

  DOI：

  10.1021/jm801006v