(3RS)-3-(4-methoxyphenyl)-1-methylpyrrolidine-2,5-dione | 32857-93-5

• 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: (3RS)-3-(4-methoxyphenyl)-1-methylpyrrolidine-2,5-dione
• 英文别名: 3-(4-methoxyphenyl)-1-methylpyrrolidine-2,5-dione；N-methyl-2-p-methoxyphenylsuccinimide；3-(4-methoxy-phenyl)-1-methyl-pyrrolidine-2,5-dione；3-(4-Methoxy-phenyl)-1-methyl-pyrrolidin-2,5-dion；N-Methyl-p-methoxy-phenyl-succinimid
• CAS: 32857-93-5
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: QQXBVFFYBRRZKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (3RS)-3-(4-methoxyphenyl)-1-methylpyrrolidine-2,5-dione 、 硼氢化钠 、 盐酸 生成 5-hydroxy-4-(4-methoxyphenyl)-1-methylpyrrolidin-2-one
  参考文献：
  名称：

  WIJNBERG J. B. P. A.; SCHOEMAKER H. E.; SPECKAMP W. N., TETRAHEDRON , 1978, 34, NO 2, 179-187

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲氧基苯乙腈 在 盐酸 、 sodium hydroxide 、 potassium carbonate 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二甲基亚砜 、 丙酮 为溶剂， 反应 1.0h， 生成 (3RS)-3-(4-methoxyphenyl)-1-methylpyrrolidine-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

• Rhodium-Catalyzed Heck-Type Coupling of Boronic Acids with Activated Alkenes in an Aqueous Emulsion
  作者：Mark Lautens、John Mancuso、Harpreet Grover

  DOI：10.1055/s-2004-829161

  日期：——

  Intermolecular couplings between arylboronic acids and activated alkenes catalyzed by a water-soluble tert-butyl amphosrhodium complex were found to progress at room temperature and generated Heck-type products with high yields and excellent selectivity. Substitution on the alkene component encouraged the formation of products arising from a conjugate addition-protonation process. In the case of Heck

  发现由水溶性叔丁基氨磷络合物催化的芳基硼酸和活化烯烃之间的分子间偶联在室温下进行，并以高产率和优异的选择性生成 Heck 型产物。烯烃组分上的取代促进了由共轭加成质子化过程产生的产物的形成。在 Heck 产物形成的情况下，必须添加两当量的烯烃组分，据信其中一当量用作牺牲氢化物受体。
• Pd(II)/bipyridine catalyzed conjugate addition of arylboronic acids to α,β-unsaturated amides
  作者：Jiamin Ji、Zhenyu Yang、Rui Liu、Yuxin Ni、Shaohui Lin、Qinmin Pan

  DOI：10.1016/j.tetlet.2016.05.022

  日期：2016.6

  The Pd(II)/bipyridine-catalyzed conjugate addition of arylboronic acid to α,β-unsaturated amides was developed and optimized, and the reaction was proceeded smoothly in air. A series of arylboronic acid and α,β-unsaturated amide substrates were surveyed, and modest to excellent yields were given.

  开发并优化了Pd（II）/联吡啶催化的芳基硼酸向α，β-不饱和酰胺的共轭加成反应，并在空气中平稳地进行了反应。调查了一系列芳基硼酸和α，β-不饱和酰胺底物，并给出了中等至极好的收率。
• Michael Addition Reactions with η²-Coordinated Anisoles:  Controlling the Stereochemistry of the Para and Benzylic Carbons
  作者：Philip L. Smith、Joseph M. Keane、Sarah E. Shankman、Mahendra D. Chordia、W. Dean Harman

  DOI：10.1021/ja047054j

  日期：2004.12.1

  the presence of a Lewis or Bronsted acid to generate stable 4H-anisolium complexes. These reactions were found to proceed with high stereochemical control with predictable outcomes, provided that the moderate acid (NH(2)Ph(2))OTf was used and the complex was dissolved in an acidic solution. The stereochemistry is shown to originate from an unexpectedly high preference for one coordination diastereomer

  在路易斯酸或布朗斯台德酸存在下，用各种迈克尔受体处理几种 eta(2) 配位的苯甲醚配合物，以生成稳定的 4H-苯甲醚配合物。发现这些反应进行高立体化学控制，结果可预测，前提是使用中度酸 (NH(2)Ph(2))OTf 并且将复合物溶解在酸性溶液中。立体化学显示源自对固态中苯甲醚络合物的一种配位非对映异构体和迈克尔反应的类狄尔斯-阿尔德过渡态的出乎意料的高度偏好。
• 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
• Osmium-Promoted Electrophilic Substitution of Anisoles:  A Versatile New Method for the Incorporation of Carbon Substituents
  作者：Stanley P. Kolis、Michael E. Kopach、Ronggang Liu、W. Dean Harman

  DOI：10.1021/jo961983e

  日期：1997.1.1

  A structurally and electronically diverse set of anisoles are dihapto-coordinated to the pi-base pentaammineosmium(II) and treated with a variety of carbon electrophiles (e.g. Michael accepters, acetals). After deprotonation of a 4H-anisolium intermediate with a tertiary amine base, C(4)-substituted anisole complexes are isolated. The functionalized arenes are removed from the metal center either by mild heating or treatment with an oxidant (e.g. AgOTf, DDQ, CAN). The resulting substituted anisoles are isolated with yields ranging from 55-95%.