1-[4-(3,5-Bis-trifluoromethyl-benzyl)-2-phenyl-piperazin-1-yl]-2-bromo-ethanone | 185110-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-[4-(3,5-Bis-trifluoromethyl-benzyl)-2-phenyl-piperazin-1-yl]-2-bromo-ethanone
• 英文别名: 1-[4-[[3,5-Bis(trifluoromethyl)phenyl]methyl]-2-phenylpiperazin-1-yl]-2-bromoethanone
• CAS: 185110-05-8
• 化学式: C₂₁H₁₉BrF₆N₂O
• 分子量: 509.289
• InChiKey: TWVXGWDAZLCVHX-UHFFFAOYSA-N

物化性质

• 沸点：
  473.2±45.0 °C(Predicted)
• 密度：
  1.486±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(4-苯基哌啶-4-基)乙酰胺 、 1-[4-(3,5-Bis-trifluoromethyl-benzyl)-2-phenyl-piperazin-1-yl]-2-bromo-ethanone 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(1-{2-[4-(3,5-Bis-trifluoromethyl-benzyl)-2-phenyl-piperazin-1-yl]-2-oxo-ethyl}-4-phenyl-piperidin-4-yl)-acetamide
  参考文献：
  名称：

  Synthesis and NK1/NK2 binding activities of a series of diacyl-substituted 2-arylpiperazines

  摘要：

  The synthesis and binding affinity for hNK(1) and hNK(2) receptors of a series of diacyl substituted 2-aryl piperazines are described. SAR evaluation led to the racemic derivative 11g as an apparent dual inhibitor. Chiral chromatographic separation of 11g led to the observation that NK1 activity was shown by one enantiomer (13a) and NK2 activity was shown by the other enantiomer (13b). X-ray crystallographic analysis of the crystalline di-BOC derivative of the NK2, active piperazine (15) showed that the 2R configuration was associated with NK2 activity. Further derivatization indicated that dual NK1/NK2 activity could be built into the 2R series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00645-5
• 作为产物：
  描述：

  2-苯基吡嗪 在 palladium diacetate 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、344.74 kPa 条件下， 反应 4.0h， 生成 1-[4-(3,5-Bis-trifluoromethyl-benzyl)-2-phenyl-piperazin-1-yl]-2-bromo-ethanone
  参考文献：
  名称：

  Synthesis and NK1/NK2 binding activities of a series of diacyl-substituted 2-arylpiperazines

  摘要：

  The synthesis and binding affinity for hNK(1) and hNK(2) receptors of a series of diacyl substituted 2-aryl piperazines are described. SAR evaluation led to the racemic derivative 11g as an apparent dual inhibitor. Chiral chromatographic separation of 11g led to the observation that NK1 activity was shown by one enantiomer (13a) and NK2 activity was shown by the other enantiomer (13b). X-ray crystallographic analysis of the crystalline di-BOC derivative of the NK2, active piperazine (15) showed that the 2R configuration was associated with NK2 activity. Further derivatization indicated that dual NK1/NK2 activity could be built into the 2R series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00645-5