1-(4-Methoxyphenyl)-3-phenylpyrrolidine-2,5-dione

• 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: 1-(4-Methoxyphenyl)-3-phenylpyrrolidine-2,5-dione
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: GXBRJKNIUHUZNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  cis-1-(p-methoxyphenyl)-4-formyl-3-phenyl-2-azetidinone 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以99%的产率得到1-(4-Methoxyphenyl)-3-phenylpyrrolidine-2,5-dione
  参考文献：
  名称：

  N-Heterocyclic Carbene Catalyzed Ring Expansion of 4-Formyl-β-lactams:  Synthesis of Succinimide Derivatives

  摘要：

  N-Heterocyclic carbene (NHC) has been employed as an efficient catalyst for ring expansion of 4-formyl-beta-lactams, allowing the facile synthesis of succinimide derivatives. This organocatalytic process features readily availability of the catalyst, low catalyst loading, and mild reaction conditions.

  DOI：

  10.1021/ol0713537

文献信息

• Ruthenium(II)-Catalyzed Hydroarylation of Maleimides Using Carboxylic Acids as a Traceless Directing Group
  作者：Anup Mandal、Harekrishna Sahoo、Suman Dana、Mahiuddin Baidya

  DOI：10.1021/acs.orglett.7b01964

  日期：2017.8.4

  ready-stock aryl carboxylic acids has been developed based on weak carboxylate-directed ortho-C–H alkylation and concomitant decarboxylation processes, fabricating 3-aryl succinimides, a recurrent scaffold in drug molecules, in high yields (up to 97%). The protocol features operational simplicity, avoids the need for precious metal additives/oxidants, and offers broad substrate scope with formal meta- and

  基于弱羧酸盐定向的邻-C-H烷基化和伴随的脱羧过程，开发了一种高效的Ru（II）催化的马来酰亚胺与现成的芳基羧酸进行加氢芳基化反应，制备了3-芳基琥珀酰亚胺，这是药物分子中的常见骨架，高产（高达97％）。该协议具有操作简单，无需贵金属添加剂/氧化剂的特点，并提供了具有正式的间位和对位选择性的广泛底物范围。它代表了Ru（II）催化马来酰亚胺与无偏苯甲酸直接芳基化的第一个例子。
• Enantioselective Synthesis of<i>cis</i>-4-Formyl-β-lactams<i>via</i>Chiral N-Heterocyclic Carbene-Catalyzed Kinetic Resolution
  作者：Gong-Qiang Li、Yi Li、Li-Xin Dai、Shu-Li You

  DOI：10.1002/adsc.200800071

  日期：2008.6.9

  An efficient synthesis of optically pure cis-4-formyl-β-lactams (up to 99% ee) by a chiral NHC-catalyzed ring expansion reaction has been realized, featuring the ready availability of both the substrate and the catalyst, and the mild reaction conditions. The current method is also suitable for the synthesis of enantioenriched 4-formyl-β-lactams and succinimides containing quaternary carbon centers

  通过手性NHC催化的扩环反应，可以高效合成光学纯的顺式-4-甲酰基-β-内酰胺（最高ee达99％），具有容易获得的底物和催化剂，并且温和的特点反应条件。当前的方法也适用于合成富含对映体的4-甲酰基-β-内酰胺和含有季碳中心的琥珀酰亚胺。
• Reversed-Phase TLC and HPLC Retention Data in Correlation Studies with in Silico Molecular Descriptors and Druglikeness Properties of Newly Synthesized Anticonvulsant Succinimide Derivatives
  作者：Nada Perisic-Janjic、Roman Kaliszan、Paweł Wiczling、Natasa Milosevic、Gordana Uscumlic、Nebojsa Banjac

  DOI：10.1021/mp100373d

  日期：2011.4.4

  constants RM0 and log kw, which characterize lipophilicity of compounds. Considering potential pharmaceutical importance of succinimide derivatives, we (i) examined the retention behavior in the reversed-phase liquid chromatographic (RP LC) systems, in both planar and column LC, and (ii) determined the relationships between chromatographic data and selected structural features of analytes that are believed

  已经研究了与两个新合成的琥珀酰亚胺衍生物系列的药代动力学有关的性质。所考虑的性质可以通过反相液相色谱法（TLC和HPLC技术）凭经验确定，也可以使用已建立的理论药物化学/药物设计软件进行计算。色谱技术可确定保留常数R M 0和log k w，其表征化合物的亲脂性。考虑到琥珀酰亚胺衍生物的潜在药物重要性，我们（i）在反相液相色谱（RP LC）系统中检测了液相色谱和柱液相色谱的保留行为，并且（ii）确定了色谱数据与所选结构特征之间的关系被认为会显着影响其吸收，分布，代谢，排泄和毒性过程的分析物（ADMETox）。发现保留常数R M 0和log k w与计算机计算的生物活性描述符，特别是HIA（人类肠道吸收）和PPB（血浆蛋白结合）参数之间存在显着关系。在[R已推荐将所研究化合物的M 0和log k w值用于描述其亲脂性和评估药代动力学特性。鉴于这项研究的结果，新合成的琥珀酰亚胺药物符合预选药物
• Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer
  作者：Nebojša Banjac、Nemanja Trišović、Željko Vitnik、Vesna Vitnik、Nataša Valentić、Gordana Ušćumlić、Ivan Juranić

  DOI：10.1007/s00706-013-1052-1

  日期：2013.10

  Two series of 1-aryl-3-phenyl- and 1-aryl-3,3-diphenylpyrrolidine-2,5-diones were synthesized and their solvatochromic properties were studied in a set of 15 solvents of different polarity. The effect of specific and non-specific solvent-solute interactions on the position of their absorption bands was evaluated by using the solvent parameter sets of Kamlet and Taft. The interpretation of the effect of different substituent patterns on the solvatochromic properties of the investigated compounds was based on quantum chemical calculations performed by the density functional theory (DFT)/CAM-B3LYP method using the 6-311G(d,p) basis set. The theoretical absorption frequencies show very good agreement with the experimental values. The energy gaps between the HOMO and LUMO orbitals were also analyzed. It is demonstrated that different substituents change the conjugation effect and further determine the pathways of intramolecular charge transfer.
• Pd-catalyzed tandem bis-hydroaminocarbonylation of terminal alkynes for synthesis of N-aryl substituted succinimides with involvement of ionic P, O-hybrid ligand
  作者：Kai-Chun Zhao、Yi-Ying Zhuang、Tian-Hong Jing、Guang-Hui Shi、Lin Guo、Xiao-Li Zhao、Yong Lu、Ye Liu

  DOI：10.1016/j.jcat.2022.12.006

  日期：2023.1