4-phenethyl-piperazine-1-carboxylic acid ethyl ester | 33169-60-7

• 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-phenethyl-piperazine-1-carboxylic acid ethyl ester
• 英文别名: Ethyl 4-(2-phenylethyl)-1-piperazinecarboxylate；ethyl 4-(2-phenylethyl)piperazine-1-carboxylate
• CAS: 33169-60-7
• 化学式: C₁₅H₂₂N₂O₂
• 分子量: 262.352
• InChiKey: TUHSBGWTTLWJQL-UHFFFAOYSA-N

物化性质

• 沸点：
  155-158 °C(Press: 2.5 Torr)
• 密度：
  1.088±0.06 g/cm3(Predicted)
• 溶解度：
  30.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-phenethyl-piperazine-1-carboxylic acid ethyl ester 在 sodium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-[[4-(2-Phenylethyl)piperazin-1-yl]methyl]chromen-4-one
  参考文献：
  名称：

  Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands

  摘要：

  Starling from a random screening showing that 2-[(4-benzylpiperazinyl)methyl] chromone was a selective and potent sigma ligand, a series of analogues were synthesized. Introduction of a substituent on the chromone moiety, replacement of methylenes by carbonyl groups and benzyl by aryl groups decrease the affinity for sigma sites. The result obtained after introduction of various substituents on the aromatic part of the benzyl is strictly depending on the size and on the position of these substituents. Stretching of the carbon chain between the phenyl and the piperazine does not strongly modify the affinity. 2-[4-(4'-methoxy benzyl)-1-piperazinyl methyl] chromone has been tested in behavioral tests that permit to believe that such derivatives could be interesting for the treatment of psychosis. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80001-9
• 作为产物：
  描述：

  N-哌嗪甲酸乙酯 、 邻氯乙苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-phenethyl-piperazine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands

  摘要：

  Starling from a random screening showing that 2-[(4-benzylpiperazinyl)methyl] chromone was a selective and potent sigma ligand, a series of analogues were synthesized. Introduction of a substituent on the chromone moiety, replacement of methylenes by carbonyl groups and benzyl by aryl groups decrease the affinity for sigma sites. The result obtained after introduction of various substituents on the aromatic part of the benzyl is strictly depending on the size and on the position of these substituents. Stretching of the carbon chain between the phenyl and the piperazine does not strongly modify the affinity. 2-[4-(4'-methoxy benzyl)-1-piperazinyl methyl] chromone has been tested in behavioral tests that permit to believe that such derivatives could be interesting for the treatment of psychosis. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80001-9

文献信息

• JILEK J. O; METYSOVA J.; NEMEC J.; SEDIVY Z.; POMYKACEK J.; PROTIVA M., COLLECT. CZECH. CHEM. COMMUNS. <CCCC-AK>, 1975, 40, NO 11, 3386-3398
  作者：JILEK J. O、 METYSOVA J.、 NEMEC J.、 SEDIVY Z.、 POMYKACEK J.、 PROTIVA M.

  DOI：——

  日期：——
• Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands
  作者：Geneviève Baziard-Mouysset、Salouma Younes、Youssef Labssita、Marc Payard、Daniel-Henri Caignard、Marie-Claire Rettori、Pierre Renard、Bruno Pfeiffer、Béatrice Guardiola-Lemaitre

  DOI：10.1016/s0223-5234(98)80001-9

  日期：1998.6

  Starling from a random screening showing that 2-[(4-benzylpiperazinyl)methyl] chromone was a selective and potent sigma ligand, a series of analogues were synthesized. Introduction of a substituent on the chromone moiety, replacement of methylenes by carbonyl groups and benzyl by aryl groups decrease the affinity for sigma sites. The result obtained after introduction of various substituents on the aromatic part of the benzyl is strictly depending on the size and on the position of these substituents. Stretching of the carbon chain between the phenyl and the piperazine does not strongly modify the affinity. 2-[4-(4'-methoxy benzyl)-1-piperazinyl methyl] chromone has been tested in behavioral tests that permit to believe that such derivatives could be interesting for the treatment of psychosis. (C) Elsevier, Paris.