1-(2,6-二甲基苯基)吡咯烷-2-酮 | 77470-81-6

• 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: 1-(2,6-二甲基苯基)吡咯烷-2-酮
• 英文名称: 1-(2,6-dimethylphenyl)pyrrolidin-2-one
• 英文别名: 1-(2,6-xylyl)-2-pyrrolidinone
• CAS: 77470-81-6
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: MAEXDEOBDFLHEC-UHFFFAOYSA-N

物化性质

• 沸点：
  410.1±14.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2,6-二甲基苯基)吡咯烷-2-酮 在 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 1-(2,6-dimethylphenyl)-3-chloromethylenepyrrolidin-2-one
  参考文献：
  名称：

  Frolov, S. I.; Negrebetskii, V. V.; Nuridzhanyan, K. A., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 5.2, p. 834 - 838

  摘要：

  DOI：
• 作为产物：
  描述：

  5-chloropentano-2',6'-xylidide 在 sodium acetate 、 sodium iodide 作用下， 以 乙醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.5h， 生成 1-(2,6-二甲基苯基)吡咯烷-2-酮
  参考文献：
  名称：

  New antiarrhythmic agents. 6. Quantitative structure-activity relationships of aminoxylidides

  摘要：

  The synthesis and pharmacological evaluation of primary and tertiary aminoxylidides with the amino group in the 2-7 position of the acyl chain are described. 2,6-Xylidine was acylated with haloacyl halides and converted to the target compounds by direct amination or by the Gabriel procedure. Alternatively, 2,6-xylidine was coupled with keto acids, and the ketoxylidides were converted to the amines by reductive amination. The target compounds were evaluated in mice both for antiarrhythmic efficacy against chloroform-induced tachycardia and for central nervous system toxicity. Experimentally determined values of partition coefficients and pKa values were used for quantitative structure-activity analyses. While the antiarrhythmic activity could be described as a function of log P alone, the CNS toxicity was best described as a function of both log P and pKa. The results suggest that antiarrhythmic potency can be increased by increasing lipophilicity, while the therapeutic index can be improved by increasing the pKa.

  DOI：

  10.1021/jm00139a007

文献信息

• Charged ion channel blockers and methods for use
  申请人：Nocion Therapeutics, Inc.

  公开号：US10934263B2

  公开（公告）日：2021-03-02

  The invention provides compounds of Formula (I), or pharmaceutically acceptable salts thereof: The compounds, compositions, methods and kits of the invention are useful for the treatment of pain, cough, itch, and neurogenic inflammation.

  本发明提供了式（I）化合物或其药学上可接受的盐类： 本发明的化合物、组合物、方法和试剂盒可用于治疗疼痛、咳嗽、瘙痒和神经源性炎症。
• TENTHOREY, P. A.;BLOCK, A. J.;RONFELD, R. A.;MCMASTER, P. D.;BYRNES, E. W+, J. MED. CHEM., 1981, 24, N 7, 798-806
  作者：TENTHOREY, P. A.、BLOCK, A. J.、RONFELD, R. A.、MCMASTER, P. D.、BYRNES, E. W+

  DOI：——

  日期：——
• CHARGED ION CHANNEL BLOCKERS AND METHODS FOR USE
  申请人：Nocion Therapeutics, Inc.

  公开号：US20200290979A1

  公开（公告）日：2020-09-17

  The invention provides compounds of Formula (I), or pharmaceutically acceptable salts thereof: The compounds, compositions, methods and kits of the invention are useful for the treatment of pain, cough, itch, and neurogenic inflammation.
• New antiarrhythmic agents. 6. Quantitative structure-activity relationships of aminoxylidides
  作者：Paul A. Tenthorey、Alan J. Block、Robert A. Ronfeld、Paul D. McMaster、Eugene W. Byrnes

  DOI：10.1021/jm00139a007

  日期：1981.7

  The synthesis and pharmacological evaluation of primary and tertiary aminoxylidides with the amino group in the 2-7 position of the acyl chain are described. 2,6-Xylidine was acylated with haloacyl halides and converted to the target compounds by direct amination or by the Gabriel procedure. Alternatively, 2,6-xylidine was coupled with keto acids, and the ketoxylidides were converted to the amines by reductive amination. The target compounds were evaluated in mice both for antiarrhythmic efficacy against chloroform-induced tachycardia and for central nervous system toxicity. Experimentally determined values of partition coefficients and pKa values were used for quantitative structure-activity analyses. While the antiarrhythmic activity could be described as a function of log P alone, the CNS toxicity was best described as a function of both log P and pKa. The results suggest that antiarrhythmic potency can be increased by increasing lipophilicity, while the therapeutic index can be improved by increasing the pKa.
• Frolov, S. I.; Negrebetskii, V. V.; Nuridzhanyan, K. A., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 5.2, p. 834 - 838
  作者：Frolov, S. I.、Negrebetskii, V. V.、Nuridzhanyan, K. A.

  DOI：——

  日期：——

表征谱图