methyl 1-acetyl-2-benzylpyrrolidine-2-carboxylate | 1228439-56-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 1-acetyl-2-benzylpyrrolidine-2-carboxylate
• CAS: 1228439-56-2
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: OBLGYQLICGDPHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-acetyl-2-benzylpyrrolidine-2-carboxylate 在 锂硼氢 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-acetyl-2-benzylpyrrolidine-2-carbaldehyde
  参考文献：
  名称：

  Towards a KCC2 blocker pharmacophore model

  摘要：

  A multi-disciplinary approach was used to identify the first pharmacophore model for KCC2 blockers: several physico-chemical studies such as XRD and NMR were combined to molecular modelling techniques, SAR analysis and synthesis of constrained analogues in order to determine a minimal conformational space regrouping few potential bioactive conformations. These conformations were further compared to the conformational space of a different series of KCC2 blockers in order to identify the common pharmacophoric features. The synthesis of more potent analogues in this second series confirmed the usefulness of this KCC2 blocker pharmacophore model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.097
• 作为产物：
  描述：

  2-benzyl 1-(tert-butyl) 2-benzylpyrrolidine-1,2-dicarboxylate 在 盐酸 、 硫酸 、 碳酸氢钠 、 sodium carbonate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 1.01h， 生成 methyl 1-acetyl-2-benzylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  新型吡咯烷衍生物的微波辅助合成和抑菌活性

  摘要：

  微波辅助合成1-乙酰基-2-苄基吡咯烷-2-羧酸及其衍生物已得到了令人鼓舞的产率。在目标化合物的四步合成中，将2-苄基叔丁基吡咯烷-1,2-二羧酸酯用作起始化合物。产物5a-5h的结构已通过光谱法确认。根据抗微生物试验，确定1-乙酰基-2-苄基吡咯烷-2-羧酰胺5c是最有效的产物。

  DOI：

  10.1134/s107036322001020x

文献信息

• Benzyl prolinate derivatives as novel selective KCC2 blockers
  作者：Cécile Pégurier、Nathalie Bosman、Philippe Collart、Marie-Laure Delporte、Karine Leclercq、Sébastien Lengelé、Ananda Kumar Kanduluru、Stéphane Meunier、Nathalie Pacico、Lakshmana Rao Vadali、Alain Wagner、Christian Wolff、Laurent Provins

  DOI：10.1016/j.bmcl.2010.02.092

  日期：2010.4

  The discovery and optimization of a novel class of selective submicromolar KCC2 blockers is described. Details of synthesis and SAR are given together with ADME properties of selected compounds. A methylsulfone residue on the R(1) phenyl group improved the overall general pro. le of these prolinate derivatives. (C) 2010 Elsevier Ltd. All rights reserved.
• Towards a KCC2 blocker pharmacophore model
  作者：Florence Lebon、Cécile Pégurier、Marie Ledecq、Benoit Mathieu、Nathalie Bosman、Anne Frycia、Sébastien Lengelé、Kashinath Dhurke、Ananda Kumar Kanduluru、Stéphane Meunier、Alain Wagner、Christian Wolff、Laurent Provins

  DOI：10.1016/j.bmcl.2012.04.097

  日期：2012.6

  A multi-disciplinary approach was used to identify the first pharmacophore model for KCC2 blockers: several physico-chemical studies such as XRD and NMR were combined to molecular modelling techniques, SAR analysis and synthesis of constrained analogues in order to determine a minimal conformational space regrouping few potential bioactive conformations. These conformations were further compared to the conformational space of a different series of KCC2 blockers in order to identify the common pharmacophoric features. The synthesis of more potent analogues in this second series confirmed the usefulness of this KCC2 blocker pharmacophore model. (C) 2012 Elsevier Ltd. All rights reserved.
• Microwave Assisted Synthesis and Antimicrobial Activity of Novel Pyrrolidine Derivatives
  作者：K. Sreekanth、Anjali Jha

  DOI：10.1134/s107036322001020x

  日期：2020.1

  Microwave assisted synthesis of 1-acetyl-2-benzylpyrrolidine-2-carboxylic acid and its derivatives has been developed with highly encouraging yields. 2-Benzyl-tert-butylpyrrolidine-1,2-dicarboxylate is used as an initial compound in the four steps synthesis of the target compounds. Structures of the products 5a–5h have been confirmed by spectroscopic methods. According to antimicrobial tests 1-ace

  微波辅助合成1-乙酰基-2-苄基吡咯烷-2-羧酸及其衍生物已得到了令人鼓舞的产率。在目标化合物的四步合成中，将2-苄基叔丁基吡咯烷-1,2-二羧酸酯用作起始化合物。产物5a-5h的结构已通过光谱法确认。根据抗微生物试验，确定1-乙酰基-2-苄基吡咯烷-2-羧酰胺5c是最有效的产物。