3-(4-methoxyphenyl)-pyrrolidine-2,5-dione | 27950-85-2

• 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: 3-(4-methoxyphenyl)-pyrrolidine-2,5-dione
• 英文别名: 3-(4-methoxyphenyl)pyrrolidine-2,5-dione；3-(4-methoxyphenyl)succinimide；3-(4-methoxy-phenyl)-pyrrolidine-2,5-dione；3-(4-Methoxy-phenyl)-pyrrolidin-2,5-dion；p-Methoxy-phenylsuccinimid
• CAS: 27950-85-2
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: VUERSPWTPJFREJ-UHFFFAOYSA-N

物化性质

• 熔点：
  135-137 °C
• 沸点：
  418.6±45.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲氧基苯乙腈 在 盐酸 、 sodium hydroxide 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 3-(4-methoxyphenyl)-pyrrolidine-2,5-dione
  参考文献：
  名称：

  Synthesis of 3-Methylthio-4-aryl-3-pyrroline-2,5-diones and 3-Arylpyrrolidine-2,5-diones by Reaction of Nitroketene Dithioacetal with Arylacetonitriles

  摘要：

  The reaction of nitroketene dithioacetal (1a), i.e., 2,2-bis(methylthio)-1-nitroethylene, with arylacetonitriles (2a-I) in the presence of the base like sodium hydroxide gave 4-nitrobut-2-enenitriles (3a-I) which were converted into 5-hydroxyimino-4-methylthio-3-phenyl-3-pyrrolin-2-ones (4a-i) under refluxing in methanol. Title compounds (5a-i) were readily obtained by the treatment of 4a-i with hydrochloric acid and were finally led to N-methylated products (6a-I) with methyl iodide. The reduction of maleimides (4-6) with zinc dust in acetic acid afforded the corresponding 3-arylpyrrolidine-2,5-diones (7a-i) that can be converted to pharmacologycally active compounds like mesembrines.

  DOI：

  10.3987/com-01-9336

文献信息

• Selective and tunable synthesis of 3-arylsuccinimides and 3-arylmaleimides from arenediazonium tetrafluoroborates and maleimides
  作者：Zhen-Hua Yang、Zhong-Hui Chen、Yu-Long An、Sheng-Yin Zhao

  DOI：10.1039/c6ra00136j

  日期：——

  arenediazonium tetrafluoroborates and maleimides in the presence of TiCl3. The reactions generated 3-arylsuccinimides in satisfactory yields under mild reaction conditions. In addition, 3-arylmaleimides were obtained by the coupling of arenediazonium tetrafluoroborate and maleimides catalyzed by CuCl. This methodology provided the selective and tunable synthesis of two classes of products by simply

  用于合成3- arylsuccinimides A高效合成策略已经从芳基重氮四氟硼酸盐和马来酰亚胺开发的TiCl的存在3。在温和的反应条件下，反应以令人满意的产率产生了3-芳基琥珀酰亚胺。另外，通过四氟硼酸壬二唑鎓与CuCl催化的马来酰亚胺的偶联，获得了3-芳基马来酰亚胺。通过简单地切换不同的金属试剂，该方法提供了两类产品的选择性和可调谐合成。该方法简单，高效，实用。
• Microwave-enhanced rhodium-catalyzed conjugate-addition of aryl boronic acids to unprotected maleimides
  作者：Pravin S. Iyer、Meaghan M. O’Malley、Matthew C. Lucas

  DOI：10.1016/j.tetlet.2007.04.084

  日期：2007.6

  Various boronic acids were treated with a rhodium (I) catalyst enabling their 1,4-conjugate addition to unprotected maleimide. The scope of the reaction was explored to include both electron-rich and electron poor boronic acids. These reactions were also performed in the microwave resulting in reduced reaction times and improved efficiencies. Additionally, substrates that were recalcitrant under conventional

  各种硼酸用铑（I）催化剂处理，可将其1,4-共轭物添加到未保护的马来酰亚胺中。探索反应的范围以包括富电子和弱电子的硼酸。这些反应也在微波中进行，从而缩短了反应时间并提高了效率。另外，在常规条件下难降解的底物在微波条件下成功反应。该反应用具有游离OH或NH基团的硼酸令人满意地进行。
• 一种3-(4-甲氧基苯基)琥珀酰亚胺的制备方法
  申请人：东华大学

  公开号：CN103936647B

  公开（公告）日：2016-02-17

  本发明涉及一种3-(4-甲氧基苯基)琥珀酰亚胺的制备方法，包括：将苯甲醚、马来酰亚胺、路易斯酸加入溶剂中，加热回流反应3-20h，然后加入2N盐酸，搅拌，抽滤，重结晶，得到3-(4-甲氧基苯基)琥珀酰亚胺。本发明制备的3-(4-甲氧基苯基)琥珀酰亚胺收率高，价格便宜，反应操作简单，反应路线短，三废少，易于工业化生产。
• Anticonvulsants. IV. An Investigation of α-(Substituted phenyl)-succinimides
  作者：C. A. Miller、Loren M. Long

  DOI：10.1021/ja01120a044

  日期：1953.12
• Synthesis of 3-Methylthio-4-aryl-3-pyrroline-2,5-diones and 3-Arylpyrrolidine-2,5-diones by Reaction of Nitroketene Dithioacetal with Arylacetonitriles
  作者：Yasuhiro Shigemitsu、Yoshinori Tominaga

  DOI：10.3987/com-01-9336

  日期：——

  The reaction of nitroketene dithioacetal (1a), i.e., 2,2-bis(methylthio)-1-nitroethylene, with arylacetonitriles (2a-I) in the presence of the base like sodium hydroxide gave 4-nitrobut-2-enenitriles (3a-I) which were converted into 5-hydroxyimino-4-methylthio-3-phenyl-3-pyrrolin-2-ones (4a-i) under refluxing in methanol. Title compounds (5a-i) were readily obtained by the treatment of 4a-i with hydrochloric acid and were finally led to N-methylated products (6a-I) with methyl iodide. The reduction of maleimides (4-6) with zinc dust in acetic acid afforded the corresponding 3-arylpyrrolidine-2,5-diones (7a-i) that can be converted to pharmacologycally active compounds like mesembrines.