N-methyl-3-(phenoxymethyl)pyrrolidine-2,5-dione | 1393661-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-methyl-3-(phenoxymethyl)pyrrolidine-2,5-dione
• 英文别名: 1-Methyl-3-(phenoxymethyl)pyrrolidine-2,5-dione；1-methyl-3-(phenoxymethyl)pyrrolidine-2,5-dione
• CAS: 1393661-21-6
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: UWAUZTDQASKUGE-UHFFFAOYSA-N

物化性质

• 沸点：
  380.4±15.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  3
• 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

• 作为产物：
  描述：

  N-甲基马来酰亚胺 、 苯氧乙酸 在 P₂₅ 作用下， 以 乙腈 为溶剂， 以23%的产率得到N-methyl-3-(phenoxymethyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  Photocatalysis in an NMR tube: Carbon–carbon coupling of phenoxyacetic acid with N-substituted maleimides

  摘要：

  The semiconductor-sensitised photocatalytic (SPC) carbon-carbon coupling of phenoxyacetic acid (PAA) and N-methylmaleimide (NMI) or maleimide (MI) has recently been reported and is studied in more detail. Irradiations are performed on a much smaller scale than commonly used, i.e. 1 mL of reaction solution in a sol-gel titania coated NMR tube, and NMR is used to monitor the progress of the various photoreactions. Use of an NMR tube as the photoreactor allows much faster reaction times (ca. 10 times faster than the 40 mL scale reaction), and helps avoid the more usual need for sample-taking and pre-treatment, before analysis by NMR, HPLC etc. The photochemistries and photocatalytic processes associated with the individual reactants (i.e. PAA and NMI or MI) reveal the production of significant products which are largely absent in the SPC-sensitised coupling reaction. Thus, when both PM and NMI or MI are irradiated together, in the study of the coupling reaction the two main products formed are: 1-methyl-3-(phenoxymethyl)pyrrolidine-2,5-dione (the adduct product), and 2methyl-3a,4-dihydrochromeno[3,4-c]pyrrole-1,3(2H,9bH)-dione (the cyclic product), which are formed in reasonable yields up to 67% and 15% respectively after only 15 min (I=3.5 mW cm(-2) per photoreactor hemisphere). Despite the well-known photochemical feature of NMI to form dimers efficiently, this work demonstrates that the background photochemistry and photocatalysis associated with the individual reactants, PM and NMI, in the photocatalysed coupling reaction are minimal due to the faster SPC kinetics for the coupling reaction, and the UV-filter effect of the sal-gel titania coating. The additional formation of organic polymeric material in all the photocatalytic processes studied is discussed briefly. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2013.06.002

文献信息

• Titania-Promoted Carboxylic Acid Alkylations of Alkenes and Cascade Addition–Cyclizations
  作者：David W. Manley、Roy T. McBurney、Phillip Miller、John C. Walton、Andrew Mills、Christopher O’Rourke

  DOI：10.1021/jo4027929

  日期：2014.2.7

  electron-deficient alkenes. The efficiency of alkylation varied appreciably with substituents in the carboxylic acids. The reactions of aryloxyacetic acids with maleimides resulted in a cascade process in which a pyrrolochromene derivative accompanied the alkylated succinimide. The selectivity for one or other of these products could be tuned to some extent by employing the photoredox catalyst under different

  使用 TiO 2 的光化学反应和羧酸在干燥厌氧条件下导致几种类型的 C-C 键形成过程与缺电子烯烃。烷基化的效率随羧酸中的取代基而显着变化。芳氧基乙酸与马来酰亚胺的反应导致了一个级联过程，其中吡咯并色烯衍生物伴随着烷基化的琥珀酰亚胺。通过在不同条件下使用光氧化还原催化剂，可以在一定程度上调整这些产品中的一种或其他产品的选择性。通过包含 2-烯基、2-芳基或 2-肟基官能团而适用于分子内闭环的芳氧基乙酸反应相当差。这些系统的反应物消耗和产物形成的概况是通过原位核磁共振监测技术获得的。对一系列不同的催化剂形式进行了效率和易用性测试。所提出的机制，涉及在 TiO2 上的空穴捕获2表面由羧酸盐随后 CO 2损失得到中间体的 EPR 光谱证据的支持。氘标记表明二氧化钛可能从表面羟基提供质子并提供电子和空穴，因此既是催化剂又是反应伙伴。
• Photocatalytic Conversion of Lignin Models into Functionalized Aromatic Molecules Initiated by the Proton-Coupled Electron Transfer Process
  作者：Yi Li、Jingya Wen、Simeng Wu、Sha Luo、Chunhui Ma、Shujun Li、Zhijun Chen、Shouxin Liu、Bing Tian

  DOI：10.1021/acs.orglett.4c00026

  日期：2024.2.16

  achieved via photocatalysis. This protocol exhibits a broad scope of lignin models and excellent compatibility of functionalization reagents, constructing a series of functionalized lignin-based aromatic compounds. Highly selective formation of alkyl radical species through a proton-coupled electron transfer and β-scission process provides the opportunity to form new C–C and C–N bonds by reaction with

  通过光催化实现了一种温和有效的木质素 β-O-4 裂解和功能化方法。该方案展示了广泛的木质素模型和功能化试剂的良好兼容性，构建了一系列功能化的木质素基芳香族化合物。通过质子耦合电子转移和β-断裂过程高度选择性地形成烷基自由基物种，提供了通过与亲电试剂反应形成新的C-C和C-N键的机会。
• Unconventional Titania Photocatalysis: Direct Deployment of Carboxylic Acids in Alkylations and Annulations
  作者：David W. Manley、Roy T. McBurney、Phillip Miller、Russell F. Howe、Shona Rhydderch、John C. Walton

  DOI：10.1021/ja306168h

  日期：2012.8.22

  Under dry, anaerobic conditions, TiO2 photocatalysis of carboxylic add precursors resulted in carbon-carbon bond-forming processes. High yields of dirners were obtained from TiO2 treatment of carboxylic acids alone: On inclusion of electron-deficient alkenes, efficient alkylations were achieved with methoxymethyl and phenoxymethyl radicals. In reactions with maleic anhydride or maleimides, phenoxyacetic acid produced chromenedione derivatives in addition to adducts. These photocatalytic reactions are simple and cheap to perform, and the TiO2 is easily removed by filtration. The anaerobic photocatalysis strategy offers a range of synthetic possibilities.
• Photocatalysis in an NMR tube: Carbon–carbon coupling of phenoxyacetic acid with N-substituted maleimides
  作者：Andrew Mills、Christopher O’Rourke

  DOI：10.1016/j.jphotochem.2013.06.002

  日期：2013.9

  The semiconductor-sensitised photocatalytic (SPC) carbon-carbon coupling of phenoxyacetic acid (PAA) and N-methylmaleimide (NMI) or maleimide (MI) has recently been reported and is studied in more detail. Irradiations are performed on a much smaller scale than commonly used, i.e. 1 mL of reaction solution in a sol-gel titania coated NMR tube, and NMR is used to monitor the progress of the various photoreactions. Use of an NMR tube as the photoreactor allows much faster reaction times (ca. 10 times faster than the 40 mL scale reaction), and helps avoid the more usual need for sample-taking and pre-treatment, before analysis by NMR, HPLC etc. The photochemistries and photocatalytic processes associated with the individual reactants (i.e. PAA and NMI or MI) reveal the production of significant products which are largely absent in the SPC-sensitised coupling reaction. Thus, when both PM and NMI or MI are irradiated together, in the study of the coupling reaction the two main products formed are: 1-methyl-3-(phenoxymethyl)pyrrolidine-2,5-dione (the adduct product), and 2methyl-3a,4-dihydrochromeno[3,4-c]pyrrole-1,3(2H,9bH)-dione (the cyclic product), which are formed in reasonable yields up to 67% and 15% respectively after only 15 min (I=3.5 mW cm(-2) per photoreactor hemisphere). Despite the well-known photochemical feature of NMI to form dimers efficiently, this work demonstrates that the background photochemistry and photocatalysis associated with the individual reactants, PM and NMI, in the photocatalysed coupling reaction are minimal due to the faster SPC kinetics for the coupling reaction, and the UV-filter effect of the sal-gel titania coating. The additional formation of organic polymeric material in all the photocatalytic processes studied is discussed briefly. (C) 2013 Elsevier B.V. All rights reserved.