2-amino-7,7-dimethyl-1-(4-fluorophenyl)-1,4,5,6,7,8-hexahydro-4-(4-methoxyphenyl)-5-oxo-quinoline-3-carbonitrile | 311776-34-8

• 英文名称: 2-amino-7,7-dimethyl-1-(4-fluorophenyl)-1,4,5,6,7,8-hexahydro-4-(4-methoxyphenyl)-5-oxo-quinoline-3-carbonitrile
• 英文别名: 2-Amino-1-(4-fluorophenyl)-4-(4-methoxyphenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarbonitrile；2-amino-1-(4-fluorophenyl)-4-(4-methoxyphenyl)-7,7-dimethyl-5-oxo-6,8-dihydro-4H-quinoline-3-carbonitrile
• CAS: 311776-34-8
• 化学式: C₂₅H₂₄FN₃O₂
• 分子量: 417.483
• InChiKey: OMMORDGMCANSNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-7,7-dimethyl-1-(4-fluorophenyl)-1,4,5,6,7,8-hexahydro-4-(4-methoxyphenyl)-5-oxo-quinoline-3-carbonitrile 在 sodium azide 、 硫酸 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以17%的产率得到2-amino-1-(4-fluorophenyl)-4-(4-methoxyphenyl)-8,8-dimethyl-3-aminocarbonyl-5-oxo-4,5,6,7,8,9-hexahydro-1H-pyrido[3,2-c]azepine
  参考文献：
  名称：

  Synthesis of Hexahydro-1H-pyrido[3,2-c]azepines as Hypotensive Agents of Expected Calcium-Channel Blocking Activity

  摘要：

  Michael addition reaction of 3-(4-fluorophenylamino)-2-cyclohexenone and its 5,5-dimethyl derivative to the acrylonitrile derivatives afforded the novel hexahydroquinolines. The target hexahydro-1H-pyrido[3,2-c]azepine derivatives were obtained via ring enlargement of the corresponding hexahydroquinolines under Schmedt conditions.Some novel pyrido[3,2-c]azepines showed hypotensive activity in vivo on normotensive anaesthetized male adult albino rats and their effects on the ventricular contraction and auricular rate of isolated rabbit hearts using Langendorff's method and nefidipine as a reference drug were studied. Compounds 29 and 36 which bear some structural similarities to nefidipine exhibited the highest hypotensive activity and negative inotropic as well as chronotropic activities.

  DOI：

  10.1007/s00706-007-0586-5
• 作为产物：
  描述：

  (4-甲氧基苄烯)丙二腈 、 3-(4-氟苯胺基)-5,5-二甲基环己-2-烯-1-酮 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 2-amino-7,7-dimethyl-1-(4-fluorophenyl)-1,4,5,6,7,8-hexahydro-4-(4-methoxyphenyl)-5-oxo-quinoline-3-carbonitrile
  参考文献：
  名称：

  Synthesis of Hexahydro-1H-pyrido[3,2-c]azepines as Hypotensive Agents of Expected Calcium-Channel Blocking Activity

  摘要：

  Michael addition reaction of 3-(4-fluorophenylamino)-2-cyclohexenone and its 5,5-dimethyl derivative to the acrylonitrile derivatives afforded the novel hexahydroquinolines. The target hexahydro-1H-pyrido[3,2-c]azepine derivatives were obtained via ring enlargement of the corresponding hexahydroquinolines under Schmedt conditions.Some novel pyrido[3,2-c]azepines showed hypotensive activity in vivo on normotensive anaesthetized male adult albino rats and their effects on the ventricular contraction and auricular rate of isolated rabbit hearts using Langendorff's method and nefidipine as a reference drug were studied. Compounds 29 and 36 which bear some structural similarities to nefidipine exhibited the highest hypotensive activity and negative inotropic as well as chronotropic activities.

  DOI：

  10.1007/s00706-007-0586-5

文献信息

• Uncatalyzed and Solvent‐Free Process for the Synthesis of 1,4‐Diarylquinoline Derivatives
  作者：Xiang‐Shan Wang、Mei‐Mei Zhang、Hong Jiang、Chang‐Sheng Yao、Shu‐Jiang Tu

  DOI：10.1080/00397910801916397

  日期：2008.4

  The uncatalyzed and three-component reaction of arylaldehyde, malonodinitrile, and 3-arylamino-5,5-dimethylcyclohex-2-enone at 160 degrees C under solvent-free conditions gave 1,4-diarylquinoline derivatives in high yields.