(S)-3-(2-oxopropyl)-1-phenylpyrrolidine-2,5-dione | 1233703-72-4

• 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: (S)-3-(2-oxopropyl)-1-phenylpyrrolidine-2,5-dione
• 英文别名: (3S)-3-(2-oxopropyl)-1-phenylpyrrolidine-2,5-dione
• CAS: 1233703-72-4
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: LJRLQDDMPCSSFL-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-苯基马来酰亚胺 、 丙酮 在 N-((1R,2R)-2-amino-1,2-diphenylethyl)-2,6-dichlorobenzenesulfonamide 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以87%的产率得到(S)-3-(2-oxopropyl)-1-phenylpyrrolidine-2,5-dione
  参考文献：
  名称：

  双官能单磺酰基DPEN盐催化的酮向马来酰亚胺的对映体选择性迈克尔加成反应。

  摘要：

  据报道，由简单的双官能伯胺单磺酰基DPEN盐催化的各种酮向马来酰亚胺的对映体选择性迈克尔加成反应是前所未有的，并以良好的对等收率（高达99％）和优异的对映选择性（高达99％）提供了所需的加合物。

  DOI：

  10.1039/c0cc00774a

文献信息

• Chiral C ₂ ‐symmetric bis‐thioureas as enzyme mimics in enantioselective Michael addition
  作者：Harold Cruz、Felipe A. Servín、Gerardo Aguirre、Sergio Pérez、Domingo Madrigal、Daniel Chávez、Andrew L. Cooksy、Ratnasamy Somanathan

  DOI：10.1002/chir.23438

  日期：2022.6

  We report herein the synthesis and application of enantiopure C2-symmetric primary amine-1,3-bis-thiourea organocatalysts in enantioselective conjugate 1,4-Michael addition of carbonyl containing nucleophiles, to nitroalkenes and N-phenylmaleimide, leading to final products in good enantioselectivities (up to 99%) and yields (up to 99%). We propose supramolecular noncovalent interactions within the

  我们在此报道了对映体纯 C 2 -对称伯胺-1,3-双硫脲有机催化剂在对映选择性共轭 1,4-Michael 加成含羰基亲核试剂中的合成和应用，与硝基烯烃和N-苯基马来酰亚胺形成最终产物良好的对映选择性（高达 99%）和产率（高达 99%）。我们提出了通过氢键在有机催化剂的底物和催化剂之间的裂缝内的超分子非共价相互作用。因此，超分子相互作用降低了模拟酶的过渡态能量。我们的实验结果背后的机制得到了理论计算的支持。
• Michael Addition of Ketones and Aldehydes to Maleimides Catalyzed by Modularly Designed Organocatalysts
  作者：Savitha Muramulla、Jun-An Ma、John Cong-Gui Zhao

  DOI：10.1002/adsc.201300041

  日期：2013.5.3

  primary α‐amino acids and Cinchona alkaloid thioureas were found to be excellent catalysts for the stereoselective Michael addition of enolizable ketones and aldehydes to maleimides. Using an MDO formed from quinidine thiourea and L‐2‐chlorophenylglycine, the corresponding Michael addition products, 3‐substituted succinimides, may be obtained in excellent yields and high enantio‐ and diastereoselectivities

  形成模块化设计有机催化剂（MDO）的原位从自组装的初生α氨基酸和金鸡纳生物碱硫脲被发现是用于立体选择性迈克尔加成烯醇化的酮和醛到马来酰亚胺的优异催化剂。使用由奎尼丁硫脲和L -2-氯苯基甘氨酸形成的MDO ，可以以优异的收率，高对映异构和非对映选择性获得相应的迈克尔加成产物3取代的琥珀酰亚胺。
• Asymmetric Conjugate Addition of Ketones to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
  作者：Alejandro Torregrosa-Chinillach、Rafael Chinchilla

  DOI：10.3390/molecules27196668

  日期：——

  Enantioenriched substituted succinimides are interesting compounds, and their asymmetric organocatalytic synthesis by the conjugated addition of ketones to maleimides has been scarcely explored. This study shows the enantioselective conjugate addition of ketones to maleimides organocatalyzed by a simple primary amine-salicylamide derived from a chiral trans-cyclohexane-1,2-diamine, which provides the

  对映体富集的取代琥珀酰亚胺是有趣的化合物，通过将酮与马来酰亚胺共轭加成来进行不对称有机催化合成的研究很少。本研究显示了酮对马来酰亚胺的对映选择性共轭加成反应，该反应由衍生自手性反式-环己烷-1,2-二胺的简单伯胺-水杨酰胺有机催化，以良好至优异的产率（高达 98%）提供所需的琥珀酰亚胺，并且具有中等至极好的对映选择性（高达 99%）。
• Asymmetric Conjugate Addition of Ketones to Maleimides Using Diaminomethyleneindenedione Organocatalyst
  作者：Tsuyoshi Miura、Kosuke Nakashima、Masahiro Kawada、Shin-ichi Hirashima、Mana Kato、Yuji Koseki

  DOI：10.1055/s-0034-1380382

  日期：——

  A novel diaminomethyleneindenedione (DMI) organocatalyst efficiently promotes the asymmetric conjugate addition of a ketone to a maleimide to afford the corresponding addition product in a high yield with up to 99% enantiomeric excess.
• Stereoselective conjugate addition of carbonyl compounds to maleimides using a diaminomethyleneindenedione organocatalyst
  作者：Kosuke Nakashima、Masahiro Kawada、Shin-ichi Hirashima、Ayako Kosugi、Mana Kato、Akihiro Yoshida、Yuji Koseki、Tsuyoshi Miura

  DOI：10.1016/j.tetasy.2016.07.002

  日期：2016.10

  A diaminomethyleneindenedione motif can serve as an excellent double hydrogen bonding donor. Bifunctional chiral primary amine 3 bearing a diaminomethyleneindenedione motif is an excellent organocatalyst to promote the asymmetric conjugate additions of various carbonyl compounds to maleimides in high yields with up to 99% ee. (C) 2016 Elsevier Ltd. All rights reserved.