3-(5-氯-2-甲氧基苯基)-5-甲基异恶唑-4-羧酸乙酯 | 495417-29-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(5-氯-2-甲氧基苯基)-5-甲基异恶唑-4-羧酸乙酯
• 英文名称: ethyl 3-(5-chloro-2-methoxyphenyl)-5-methylisoxazole-4-carboxylate
• 英文别名: ethyl 3-(5-chloro-2-methoxyphenyl)-5-methyl-1,2-oxazole-4-carboxylate
• CAS: 495417-29-3
• 化学式: C₁₄H₁₄ClNO₄
• 分子量: 295.722
• InChiKey: MEMVMIGLWPPCEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(5-氯-2-甲氧基苯基)-5-甲基异恶唑-4-羧酸乙酯 在 ammonium hydroxide 、 lithium aluminium tetrahydride 、 magnesium sulfate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 70.0h， 生成 4-[3-(5-Chloro-2-methoxy-phenyl)-5-methyl-isoxazol-4-yl]-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Unique Structure−Activity Relationship for 4-Isoxazolyl-1,4-dihydropyridines

  摘要：

  A series of 4-isoxazolyl-1,4-dihydropyridines (IDs) were prepared and characterized, and their interaction with the calcium channel was studied by patch clamp analysis. The structure-ctivity relationship (SAR) that emerges is distinct from the 4-aryldihydropyridines (DHPs), and affinity increases dramatically at higher holding potentials. Thus, among the 3'-arylisoxazolyl analogues p-Br > p-C much greater than p-F, and p-Cl > m-Cl > o-Cl much greater than o-MeO. Four of the analogues were examined by single-crystal X-ray diffractometry, and all were found to adopt an O-exo conformation in the solid state. The calculated barrier to rotation, however, suggests that rotation about the juncture between the heterocyclic rings is plausible under physiological conditions. A variable-temperature NMR study confirmed the computation. With Striessnig's computational sequence homologation procedure, a working hypothesis was derived from the data that explains the unique SAR for IDs.

  DOI：

  10.1021/jm020354w
• 作为产物：
  描述：

  (E)-3-(1-吡咯烷酮)巴豆酸乙酯 、 5-chloro-2-methoxybenzohydroximinoyl chloride 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以64%的产率得到3-(5-氯-2-甲氧基苯基)-5-甲基异恶唑-4-羧酸乙酯
  参考文献：
  名称：

  Unique Structure−Activity Relationship for 4-Isoxazolyl-1,4-dihydropyridines

  摘要：

  A series of 4-isoxazolyl-1,4-dihydropyridines (IDs) were prepared and characterized, and their interaction with the calcium channel was studied by patch clamp analysis. The structure-ctivity relationship (SAR) that emerges is distinct from the 4-aryldihydropyridines (DHPs), and affinity increases dramatically at higher holding potentials. Thus, among the 3'-arylisoxazolyl analogues p-Br > p-C much greater than p-F, and p-Cl > m-Cl > o-Cl much greater than o-MeO. Four of the analogues were examined by single-crystal X-ray diffractometry, and all were found to adopt an O-exo conformation in the solid state. The calculated barrier to rotation, however, suggests that rotation about the juncture between the heterocyclic rings is plausible under physiological conditions. A variable-temperature NMR study confirmed the computation. With Striessnig's computational sequence homologation procedure, a working hypothesis was derived from the data that explains the unique SAR for IDs.

  DOI：

  10.1021/jm020354w