4-((1-benzylpiperidin-4-yl)(3-bromophenyl)amino)-N,N-diethylbenzamide | 1198602-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-((1-benzylpiperidin-4-yl)(3-bromophenyl)amino)-N,N-diethylbenzamide
• CAS: 1198602-05-9
• 化学式: C₂₉H₃₄BrN₃O
• 分子量: 520.512
• InChiKey: NQRZGNZRYBCOKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  26.79
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-((1-benzylpiperidin-4-yl)(3-bromophenyl)amino)-N,N-diethylbenzamide 在 二苯甲酮亚胺 、 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 、 盐酸 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 以81%的产率得到4-((3-aminophenyl)(1-benzylpiperidin-4-yl)amino)-N,N-diethylbenzamide
  参考文献：
  名称：

  Delta agonist hydroxy bioisosteres: The discovery of 3-((1-benzylpiperidin-4-yl){4-[(diethylamino)carbonyl]phenyl}amino)benzamide with improved delta agonist activity and in vitro metabolic stability

  摘要：

  We have investigated phenol replacements in a series of diaryl amino piperidine delta opioid agonists. From this study we have demonstrated that the hydroxy functional group can be replaced with a primary amide group, giving enhanced activity at the delta receptor, increased selectivity versus mu and kappa as well as improved in vitro metabolic stability. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.068
• 作为产物：
  描述：

  4-[N-(1-benzyl-piperidin-4-yl)-amino]-N,N-diethyl benzamide 、 1,3-二溴苯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 以68%的产率得到4-((1-benzylpiperidin-4-yl)(3-bromophenyl)amino)-N,N-diethylbenzamide
  参考文献：
  名称：

  Delta agonist hydroxy bioisosteres: The discovery of 3-((1-benzylpiperidin-4-yl){4-[(diethylamino)carbonyl]phenyl}amino)benzamide with improved delta agonist activity and in vitro metabolic stability

  摘要：

  We have investigated phenol replacements in a series of diaryl amino piperidine delta opioid agonists. From this study we have demonstrated that the hydroxy functional group can be replaced with a primary amide group, giving enhanced activity at the delta receptor, increased selectivity versus mu and kappa as well as improved in vitro metabolic stability. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.068