1-[4-(4-chlorobenzyloxy)-3-cyanophenyl]ethanone | 1198617-58-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-(4-chlorobenzyloxy)-3-cyanophenyl]ethanone
• 英文别名: 5-Acetyl-2-[(4-chlorophenyl)methoxy]benzonitrile
• CAS: 1198617-58-1
• 化学式: C₁₆H₁₂ClNO₂
• 分子量: 285.73
• InChiKey: UCXPOYPBNSUGQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[4-(4-chlorobenzyloxy)-3-cyanophenyl]ethanone 、 草酸二乙酯 在 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以59.7%的产率得到(Z)-ethyl 4-[4-(4-chlorobenzyloxy)-3-cyanophenyl]-2-hydroxy-4-oxobut-2-enoate
  参考文献：
  名称：

  Synthesis of some 5-phenylisoxazole-3-carboxylic acid derivatives as potent xanthine oxidase inhibitors

  摘要：

  A number of 5-phenylisoxazole-3-carboxylic acid derivatives (5a-e, 11a-e) were synthesized and analyzed for their ability to inhibit xanthine oxidase. Most of the compounds exhibited potency levels in the micromolar/submicromolar range. The presence of a cyano group at the 3-position of phenyl moiety turned out to be the preferred substitution pattern, as its transformation into the nitro group determined a general reduction of the inhibitory potency. A molecular modeling study on compound 11a was performed to gain an insight into its binding mode with xanthine oxidase, and to provide the basis for further structure-guided design of new non-purine xanthine oxidase inhibitors related with 5-phenylisoxazole-3-carboxylic acid scaffold.

  DOI：

  10.1016/j.ejmech.2010.02.013
• 作为产物：
  描述：

  1-[4-(4-chlorobenzyloxy)-3-iodophenyl]ethanone 、 copper(l) cyanide 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以79.8%的产率得到1-[4-(4-chlorobenzyloxy)-3-cyanophenyl]ethanone
  参考文献：
  名称：

  Synthesis of some 5-phenylisoxazole-3-carboxylic acid derivatives as potent xanthine oxidase inhibitors

  摘要：

  A number of 5-phenylisoxazole-3-carboxylic acid derivatives (5a-e, 11a-e) were synthesized and analyzed for their ability to inhibit xanthine oxidase. Most of the compounds exhibited potency levels in the micromolar/submicromolar range. The presence of a cyano group at the 3-position of phenyl moiety turned out to be the preferred substitution pattern, as its transformation into the nitro group determined a general reduction of the inhibitory potency. A molecular modeling study on compound 11a was performed to gain an insight into its binding mode with xanthine oxidase, and to provide the basis for further structure-guided design of new non-purine xanthine oxidase inhibitors related with 5-phenylisoxazole-3-carboxylic acid scaffold.

  DOI：

  10.1016/j.ejmech.2010.02.013