3-(3-chlorophenyl)-5-methylisoxazole-4-carboxaldehyde | 495417-37-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-chlorophenyl)-5-methylisoxazole-4-carboxaldehyde
• 英文别名: 4-Isoxazolecarboxaldehyde, 3-(3-chlorophenyl)-5-methyl-；3-(3-chlorophenyl)-5-methyl-1,2-oxazole-4-carbaldehyde
• CAS: 495417-37-3
• 化学式: C₁₁H₈ClNO₂
• 分子量: 221.643
• InChiKey: HYDJYURXCQTXCL-UHFFFAOYSA-N

物化性质

• 沸点：
  390.8±42.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酰乙酸乙酯 、 3-(3-chlorophenyl)-5-methylisoxazole-4-carboxaldehyde 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以39%的产率得到Diethyl 4-[3-(3-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  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：

  [3-(3-氯苯基)-5-甲基-1,2-恶唑-4-基]甲醇 在 magnesium sulfate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以93%的产率得到3-(3-chlorophenyl)-5-methylisoxazole-4-carboxaldehyde
  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

文献信息

• Unique Structure−Activity Relationship for 4-Isoxazolyl-1,4-dihydropyridines
  作者：Gerald W. Zamponi、Stephanie C. Stotz、Richard J. Staples、Tina M. Andro、Jared K. Nelson、Victoria Hulubei、Alex Blumenfeld、Nicholas R. Natale

  DOI：10.1021/jm020354w

  日期：2003.1.1

  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.