(S)-1-(4-fluoro-3-morpholin-4-yl-phenyl)ethylamine | 591742-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (S)-1-(4-fluoro-3-morpholin-4-yl-phenyl)ethylamine
• 英文别名: (1S)-1-(4-fluoro-3-morpholin-4-ylphenyl)ethanamine
• CAS: 591742-65-3
• 化学式: C₁₂H₁₇FN₂O
• 分子量: 224.278
• InChiKey: NEXQZVQGXDIAFM-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  肉桂酸 、 (S)-1-(4-fluoro-3-morpholin-4-yl-phenyl)ethylamine 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (E)-N-[(1S)-1-(4-fluoro-3-morpholin-4-ylphenyl)ethyl]-3-phenylprop-2-enamide
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of Acrylamides as KCNQ2 Potassium Channel Openers

  摘要：

  A new class of acrylamides was synthesized, and the effects of these analogues on outward potassium current were evaluated by using two electrode voltage clamp recordings from Xenopus laevis oocytes expressing cloned mKCNQ2 channels. SAR studies indicated that the pharmacophore of the acrylamide series includes the (S) absolute configuration at the (1-phenyl)ethyl moiety and the alpha,beta-unsaturated acrylamide functionality with a free NH. This study identified (S)-N-[1-(3-morpholin-4-yl-phenyl)-ethyl]-3-phenyl-acrylamide ((S)-1) and (S)-N-[1-(4-fluoro-3morpholin-4-yl-phenyl)-ethyl]-3-(4-fluoro-phenyl)-acrylamide ((S)-2) as KCNQ2 openers for further electrophysiological evaluations. These two acrylamides demonstrated significant activity in the cortical spreading depression model of migraine as we reported previously.

  DOI：

  10.1021/jm0305826
• 作为产物：
  描述：

  3-溴-4-氟苯甲酮 在 palladium on activated charcoal 、 Ra-Ni palladium diacetate 、 氢气 、 甲酸铵 、 四氯化钛 、 caesium carbonate 、 三乙胺 、 2-(二叔丁基膦)联苯 作用下， 以 甲醇 、 甲苯 、 苯 为溶剂， 80.0 ℃ 、206.84 kPa 条件下， 反应 31.0h， 生成 (S)-1-(4-fluoro-3-morpholin-4-yl-phenyl)ethylamine
  参考文献：
  名称：

  Synthesis of fluorinated 1-(3-Morpholin-4-yl-phenyl)-Ethylamines

  摘要：

  The synthesis of four (+/-)-fluorinated 1-(3-morpholin-4-yl-phenyl)-ethylamines and an enantioselective approach to these amines through reductive amination are described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00240-3

文献信息

• Synthesis of fluorinated 1-(3-Morpholin-4-yl-phenyl)-Ethylamines
  作者：Yong-Jin Wu、Huan He、Li-Qiang Sun、Dedong Wu、Qi Gao、Hui-Yin Li

  DOI：10.1016/s0960-894x(03)00240-3

  日期：2003.5

  The synthesis of four (+/-)-fluorinated 1-(3-morpholin-4-yl-phenyl)-ethylamines and an enantioselective approach to these amines through reductive amination are described. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis and Structure−Activity Relationship of Acrylamides as KCNQ2 Potassium Channel Openers
  作者：Yong-Jin Wu、Huan He、Li-Qiang Sun、Alexandre L'Heureux、Jie Chen、Pierre Dextraze、John E. Starrett,、Christopher G. Boissard、Valentin K. Gribkoff、Joanne Natale、Steven I. Dworetzky

  DOI：10.1021/jm0305826

  日期：2004.5.1

  A new class of acrylamides was synthesized, and the effects of these analogues on outward potassium current were evaluated by using two electrode voltage clamp recordings from Xenopus laevis oocytes expressing cloned mKCNQ2 channels. SAR studies indicated that the pharmacophore of the acrylamide series includes the (S) absolute configuration at the (1-phenyl)ethyl moiety and the alpha,beta-unsaturated acrylamide functionality with a free NH. This study identified (S)-N-[1-(3-morpholin-4-yl-phenyl)-ethyl]-3-phenyl-acrylamide ((S)-1) and (S)-N-[1-(4-fluoro-3morpholin-4-yl-phenyl)-ethyl]-3-(4-fluoro-phenyl)-acrylamide ((S)-2) as KCNQ2 openers for further electrophysiological evaluations. These two acrylamides demonstrated significant activity in the cortical spreading depression model of migraine as we reported previously.