3-吡咯烷酮,1,2-二甲基-,(2S)- | 172792-66-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 3-吡咯烷酮,1,2-二甲基-,(2S)-
• 英文名称: (2S)-1,2-Dimethylpyrrolidin-3-one
• CAS: 172792-66-4
• 化学式: C₆H₁₁NO
• 分子量: 113.159
• InChiKey: VEUYRZJQDCCKKP-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-吡咯烷酮,1,2-二甲基-,(2S)- 在 iron(III) chloride on silica 、 叔丁基锂 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 (2S)-3-(6-fluoronaphthalen-2-yl)-1,2-dimethyl-2,5-dihydropyrrole
  参考文献：
  名称：

  Microwave assisted synthesis of chiral pyrrolines with biological activity

  摘要：

  A new, high yield regioselective reaction affording racemic and enantiomeric 1,2-dimethyl-3-[2-(6-substituted naphthyl)]-2H,5H-pyrrolines is reported. Compounds were provided by dehydration of the corresponding 1,2-dimethyl-3[2-(6-substituted naphthyl)]-3-hydroxy-pyrrolidines under microwave irradiation and solvent-free conditions. Pharmacological properties of enantiomeric compounds are also described; the analgesic activity was investigated by the hot plate test. A conformational analysis of the compounds was carried out by molecular modeling techniques with the aim to get information about the fitting to known analgesic pharmacophore models. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.001

文献信息

• Chiral arylpyrrolidinols: preparation and biological profile
  作者：Simona Collina、Daniela Rossi、Guya Loddo、Annalisa Barbieri、Enrica Lanza、Laura Linati、Stefano Alcaro、Andrea Gallelli、Ornella Azzolina

  DOI：10.1016/j.bmc.2005.02.054

  日期：2005.5

  The preparation and biological evaluation of a new class of arylpyrrolidinols is reported. The antinociceptive activity was evaluated in vivo with the hot plate test (HPT) and formalin test (FT), excluding any involvement on motor coordination with the rota-rod test (RRT). The nociceptive behavior in the late phase of FT (representative of chronic pain) suggests an involvement of the antiinflammatory process and it is clearly influenced by the stereochemical features, being the eutomer of phenylpyrrolidinols, the (2R,3S) enantiomer. Despite this, a specific mechanism of action is not yet clarified. (c) 2005 Elsevier Ltd. All rights reserved.
• Microwave assisted synthesis of chiral pyrrolines with biological activity
  作者：Simona Collina、Guya Loddo、Annalisa Barbieri、Laura Linati、Stefano Alcaro、Paola Chimenti、Ornella Azzolina

  DOI：10.1016/j.tetasy.2004.10.001

  日期：2004.11

  A new, high yield regioselective reaction affording racemic and enantiomeric 1,2-dimethyl-3-[2-(6-substituted naphthyl)]-2H,5H-pyrrolines is reported. Compounds were provided by dehydration of the corresponding 1,2-dimethyl-3[2-(6-substituted naphthyl)]-3-hydroxy-pyrrolidines under microwave irradiation and solvent-free conditions. Pharmacological properties of enantiomeric compounds are also described; the analgesic activity was investigated by the hot plate test. A conformational analysis of the compounds was carried out by molecular modeling techniques with the aim to get information about the fitting to known analgesic pharmacophore models. (C) 2004 Elsevier Ltd. All rights reserved.