tert-butyl (3S)-3-[(2,3-dichlorobenzyl)amino]pyrrolidine-1-carboxylate | 892388-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (3S)-3-[(2,3-dichlorobenzyl)amino]pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (3S)-3-[(2,3-dichlorophenyl)methylamino]pyrrolidine-1-carboxylate
• CAS: 892388-59-9
• 化学式: C₁₆H₂₂Cl₂N₂O₂
• 分子量: 345.269
• InChiKey: IKDKEVXVFVDALR-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S)-3-[(2,3-dichlorobenzyl)amino]pyrrolidine-1-carboxylate 、 异戊酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 tert-butyl (S)-3-(N-(2,3-dichlorobenzyl)-3-methylbutanamido)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  N-Benzyl-N-(pyrrolidin-3-yl)carboxamides as a new class of selective dual serotonin/noradrenaline reuptake inhibitors

  摘要：

  The structure-activity relationship and the synthesis of novel N-benzyl-N-(pyrrolidin-3-yl)carboxamides as dual serotonin (5-HT) and noradrenaline (NA) monoamine reuptake inhibitors are described. Compounds such as 18 exhibited dual 5-HT and NA reuptake inhibition, good selectivity over dopamine (DA) reuptake inhibition and drug-like physicochemical properties consistent with CNS target space. Compound 18 was selected for further preclinical evaluation. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.078
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 tert-butyl (3S)-3-[(2,3-dichlorobenzyl)amino]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  N-Benzyl-N-(pyrrolidin-3-yl)carboxamides as a new class of selective dual serotonin/noradrenaline reuptake inhibitors

  摘要：

  The structure-activity relationship and the synthesis of novel N-benzyl-N-(pyrrolidin-3-yl)carboxamides as dual serotonin (5-HT) and noradrenaline (NA) monoamine reuptake inhibitors are described. Compounds such as 18 exhibited dual 5-HT and NA reuptake inhibition, good selectivity over dopamine (DA) reuptake inhibition and drug-like physicochemical properties consistent with CNS target space. Compound 18 was selected for further preclinical evaluation. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.078

文献信息

• N-Benzyl-N-(pyrrolidin-3-yl)carboxamides as a new class of selective dual serotonin/noradrenaline reuptake inhibitors
  作者：Florian Wakenhut、Paul V. Fish、M. Jonathan Fray、Ian Gurrell、James E. Mills、Alan Stobie、Gavin A. Whitlock

  DOI：10.1016/j.bmcl.2008.06.078

  日期：2008.8

  The structure-activity relationship and the synthesis of novel N-benzyl-N-(pyrrolidin-3-yl)carboxamides as dual serotonin (5-HT) and noradrenaline (NA) monoamine reuptake inhibitors are described. Compounds such as 18 exhibited dual 5-HT and NA reuptake inhibition, good selectivity over dopamine (DA) reuptake inhibition and drug-like physicochemical properties consistent with CNS target space. Compound 18 was selected for further preclinical evaluation. (c) 2008 Elsevier Ltd. All rights reserved.