4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-2-(4-hydroxy-(2E)-butenyloxy)methyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine | 138078-47-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-2-(4-hydroxy-(2E)-butenyloxy)methyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine
• 英文别名: 3-O-ethyl 5-O-methyl 4-(2,3-dichlorophenyl)-2-[[(E)-4-hydroxybut-2-enoxy]methyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 138078-47-4
• 化学式: C₂₂H₂₅Cl₂NO₆
• 分子量: 470.35
• InChiKey: JLLABMYAYZEXLC-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  ethyl 4<<4-(2,3-dichlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridin-2-yl>methoxy>-2-butynoate 在 lithium aluminium tetrahydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.25h， 生成 4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-2-(4-hydroxy-(2E)-butenyloxy)methyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine
  参考文献：
  名称：

  Long-acting dihydropyridine calcium antagonists. 7. Compounds containing unsaturation in the 2-substituent on the 1,4-dihydropyridine ring

  摘要：

  To evaluate the effect of introducing unsaturation into the 2-substituent of 1,4-dihydropyridines related to amlodipine (1), a number of alkene and alkyne analogues were prepared and their calcium antagonist activity was assessed. For several series of compounds, in vitro potency increased in the order alkane < alkene < alkyne. This trend may either reflect decreasing entropy loss on binding to the DHP receptor or be a consequence of a favourable pi-interaction with the DHP receptor.

  DOI：

  10.1016/0223-5234(91)90197-u