1-[(S)-(2,4-dichlorophenyl)(phenyl)methyl]piperazine | 1345627-96-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[(S)-(2,4-dichlorophenyl)(phenyl)methyl]piperazine
• 英文别名: 1-[(S)-(2,4-dichlorophenyl)-phenylmethyl]piperazine
• CAS: 1345627-96-4
• 化学式: C₁₇H₁₈Cl₂N₂
• 分子量: 321.249
• InChiKey: MNZLSUXPVVAZNX-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(S)-(2,4-dichlorophenyl)(phenyl)methyl]piperazine 、 1-氨基哌啶 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 以82%的产率得到4-[(S)-(2,4-dichlorophenyl)(phenyl)methyl]-N-piperidin-1-ylpiperazine-1-carboxamide
  参考文献：
  名称：

  Asymmetric synthesis and biological evaluation of N-cyclohexyl-4-[1-(2,4-dichlorophenyl)-1-(p-tolyl)methyl]piperazine-1-carboxamide as hCB1 receptor antagonists

  摘要：

  We recently discovered and reported a novel series of benzhydrylpiperazine derivatives bearing an asymmetric carbon atom that are potent and selective hCB1 inverse agonists. In the present study, we used Davis-Ellmann-type sulfonamide chemistry to asymmetrically synthesize two enantiomers of the most potent racemic N-cyclohexyl-4-[1-(2,4-dichlorophenyl)-1-(p-tolyl)methyl]piperazine-1-carboxamide [14]. Enantiomer separation and configuration assignment were carried out. Our results indicate that the R-configuration is the more active enantiomer, displaying enhanced antagonistic activity for hCB1 receptor, better oral bioavailability, and greater efficacy in the reduction of body weight in diet-induced obese mice. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.030
• 作为产物：
  描述：

  (R)-N-(2,4-dichlorophenyl)methylene-2-methylpropane-2-sulfinamide 在 盐酸 、 potassium carbonate 、 苯硫酚 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 8.0h， 生成 1-[(S)-(2,4-dichlorophenyl)(phenyl)methyl]piperazine
  参考文献：
  名称：

  Asymmetric synthesis and biological evaluation of N-cyclohexyl-4-[1-(2,4-dichlorophenyl)-1-(p-tolyl)methyl]piperazine-1-carboxamide as hCB1 receptor antagonists

  摘要：

  We recently discovered and reported a novel series of benzhydrylpiperazine derivatives bearing an asymmetric carbon atom that are potent and selective hCB1 inverse agonists. In the present study, we used Davis-Ellmann-type sulfonamide chemistry to asymmetrically synthesize two enantiomers of the most potent racemic N-cyclohexyl-4-[1-(2,4-dichlorophenyl)-1-(p-tolyl)methyl]piperazine-1-carboxamide [14]. Enantiomer separation and configuration assignment were carried out. Our results indicate that the R-configuration is the more active enantiomer, displaying enhanced antagonistic activity for hCB1 receptor, better oral bioavailability, and greater efficacy in the reduction of body weight in diet-induced obese mice. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.030