[4-(2,4-Dimethyl-phenyl)-piperazin-1-yl]-((1R,2R)-2-phenyl-cyclopropyl)-methanone | 307952-36-9

• 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: [4-(2,4-Dimethyl-phenyl)-piperazin-1-yl]-((1R,2R)-2-phenyl-cyclopropyl)-methanone
• 英文别名: [4-(2,4-dimethylphenyl)piperazin-1-yl]-[(1R,2R)-2-phenylcyclopropyl]methanone
• CAS: 307952-36-9
• 化学式: C₂₂H₂₆N₂O
• 分子量: 334.461
• InChiKey: QEEWQDKNYXNRKV-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [4-(2,4-Dimethyl-phenyl)-piperazin-1-yl]-((1R,2R)-2-phenyl-cyclopropyl)-methanone 在 aluminium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (1R,2R)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dimethylphenyl)piperazine
  参考文献：
  名称：

  trans-1-[(2-Phenylcyclopropyl)methyl]-4-arylpiperazines:  Mixed Dopamine D₂/D₄ Receptor Antagonists as Potential Antipsychotic Agents

  摘要：

  The dopaminergic receptor profile of a series of trans-1-[(2-phenylcyclopropyl)methyl]-4-arylpiperazines was examined. Aromatic substitution patterns were varied with the goal of identifying a compound having affinities for the D-2 and D-4 receptors in a ratio similar to that observed for the atypical neuroleptic clozapine. The compounds (1S,2S)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dichlorophenyl)piperazine (5m) and (1S,2S)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dimethylphenyl)piperazine (5t) were selected for functional antagonists at D-2 and D-4 receptors and had a D-2/D-4 ratio approximating that of clozapine; they proved inactive in behavioral tests of antipsychotic activity.

  DOI：

  10.1021/jm990562x
• 作为产物：
  描述：

  trans-2-phenyl-1-cyclopropanecarbonyl chloride 在 4-二甲氨基吡啶 、 氢氧化钾 、 1-羟基苯并三唑 、 一水合肼 、 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 、 乙二醇 为溶剂， 反应 33.0h， 生成 [4-(2,4-Dimethyl-phenyl)-piperazin-1-yl]-((1R,2R)-2-phenyl-cyclopropyl)-methanone
  参考文献：
  名称：

  trans-1-[(2-Phenylcyclopropyl)methyl]-4-arylpiperazines:  Mixed Dopamine D₂/D₄ Receptor Antagonists as Potential Antipsychotic Agents

  摘要：

  The dopaminergic receptor profile of a series of trans-1-[(2-phenylcyclopropyl)methyl]-4-arylpiperazines was examined. Aromatic substitution patterns were varied with the goal of identifying a compound having affinities for the D-2 and D-4 receptors in a ratio similar to that observed for the atypical neuroleptic clozapine. The compounds (1S,2S)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dichlorophenyl)piperazine (5m) and (1S,2S)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dimethylphenyl)piperazine (5t) were selected for functional antagonists at D-2 and D-4 receptors and had a D-2/D-4 ratio approximating that of clozapine; they proved inactive in behavioral tests of antipsychotic activity.

  DOI：

  10.1021/jm990562x