1-(3-chloro-4-methoxyphenyl)-1H-pyrrole-2,5-dione | 70850-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 1-(3-chloro-4-methoxyphenyl)-1H-pyrrole-2,5-dione
• 英文别名: 1-(3-chloro-4-methoxyphenyl)-2,5-dihydro-1H-pyrrole-2,5-dione；1-(3-chloro-4-methoxyphenyl)pyrrole-2,5-dione
• CAS: 70850-16-7
• 化学式: C₁₁H₈ClNO₃
• mdl: MFCD02111570
• 分子量: 237.642
• InChiKey: XLCYQOVWGQZQRE-UHFFFAOYSA-N

物化性质

• 沸点：
  399.9±32.0 °C(Predicted)
• 密度：
  1.429±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  1-(3-chloro-4-methoxyphenyl)-1H-pyrrole-2,5-dione 、 间苯二甲醚 在 甲烷磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.5h， 以79%的产率得到1-(3-chloro-4-methoxyphenyl)-3-(2,4-dimethoxyphenyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  甲磺酸催化富电子芳烃与N-芳基马来酰亚胺的Friedel-Crafts反应：一种高效的无金属途径获得3-芳基琥珀酰亚胺

  摘要：

  Friedel–Crafts反应被广泛用于C–C键形成反应，以使富电子芳烃与具有高区域选择性的缺电子烯烃直接连接。在此，已经开发了一种高效的，无金属且对环境有益的富电子芳烃F-C策略与N-芳基马来酰亚胺，用于在绿色试剂甲磺酸存在下，温和的反应条件下构建3-芳基琥珀酰亚胺。这种高度简便，高产的协议与不同的富电子芳烃具有兼容性。

  DOI：

  10.1055/s-0040-1706008
• 作为产物：
  描述：

  3-氯-4-甲氧基苯胺 在 sodium acetate 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(3-chloro-4-methoxyphenyl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita

  摘要：

  Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 +/- 1.3, 5.1 +/- 3.4, 16.2 +/- 5.4, and 19.0 +/- 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 +/- 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at SO mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.

  DOI：

  10.1021/acs.jafc.6b02250

文献信息

• A Comprehensive Study of the Heterocyclizations of N-Arylmaleimides and 6-Aminouracils
  作者：Sergey Komykhov、Valentin Chebanov、Roman Rudenko、Sergey Desenko、Yulia Sen’ko、Oleg Shishkin、Irina Konovalova、Svetlana Shishkina

  DOI：10.1055/s-0030-1260163

  日期：2011.10

  Heterocyclization reactions between N-arylmaleimides and 6-aminouracils were studied in detail. It was established that several directions are possible depending on the nature of reaction medium and the substituent character in the uracil component. The synthetic procedure leading to N-phenyl-2,4,7-trioxopyrido[2,3-d]pyrimidine-5-carboxamides in good-to-high yields was developed and key stages of the corresponding reaction were established.

  详细研究了 N-芳基马来酰亚胺和 6-氨基脲嘧啶之间的异环化反应。根据反应介质的性质和尿嘧啶成分中取代基的特性，确定了几个可能的反应方向。研究人员开发了一种合成程序，可以高产率合成 N-苯基-2,4,7-三氧吡啶并[2,3-d]嘧啶-5-甲酰胺，并确定了相应反应的关键阶段。
• Diverse Directions of Heterocyclizations Involving Derivatives of 5-Aminopyrazoles and N-Arylmaleimides
  作者：Sergey Komykhov、Valentin Chebanov、Roman Rudenko、Sergey Desenko、Vladimir Musatov、Oleg Shishkin、Irina Konovalova、Elena Vashchenko

  DOI：10.1055/s-0030-1258421

  日期：2011.3

  Heterocyclization reactions between derivatives of 5-aminopyrazoles and N-arylmaleimides were studied and it was established that several directions are possible. Cyclizations involving 1,3-unsubstituted 5-aminopyrazoles yielded mixtures of two regioisomeric compounds, pyrazolo[1,5-a]pyrimidine-7-carboxamides and pyrazolo[3,4-b]pyridine-4-carboxamides. Reactions of 4-substituted 5-aminopyrazoles in boiling acetic acid or N,N-dimethylformamide in most cases gave pyrazolo[1,5-a]pyrimidine-7-carboxamides as the sole product. The treatment of 1-substituted 5-aminopyrazoles with maleimides possesses high selectivity only in N,N-dimethylformamide yielding pyrazolopyridines while in acetic acid the formation mixtures with pyrrolopyrazolones is observed. The key intermediates of the reaction studied were isolated and discussed.

  研究人员对 5-氨基吡唑衍生物和 N-芳基马来酰亚胺之间的异环化反应进行了研究，并确定了几个可能的方向。涉及 1,3- 未取代的 5-氨基吡唑的环化反应产生了两种异构体的混合物，即吡唑并[1,5-a]嘧啶-7-羧酰胺和吡唑并[3,4-b]吡啶-4-羧酰胺。在大多数情况下，4-取代的 5-氨基吡唑在沸腾的乙酸或 N,N-二甲基甲酰胺中反应生成的唯一产物是吡唑并[1,5-a]嘧啶-7-羧酰胺。用马来酰亚胺处理 1-取代的 5-氨基吡唑，只有在 N,N-二甲基甲酰胺中才具有高选择性，生成吡唑并吡啶，而在乙酸中则会与吡咯并吡唑酮形成混合物。对所研究反应的关键中间产物进行了分离和讨论。
• Elektronenstrahlvernetzbare Resistlacke
  申请人：BAYER AG

  公开号：EP0001997B1

  公开（公告）日：1981-02-11
• Potent Nematicidal Activity of Maleimide Derivatives on <i>Meloidogyne incognita</i>
  作者：Kodjo Eloh、Monica Demurtas、Manuel Giacomo Mura、Alessandro Deplano、Valentina Onnis、Nicola Sasanelli、Andrea Maxia、Pierluigi Caboni

  DOI：10.1021/acs.jafc.6b02250

  日期：2016.6.22

  Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 +/- 1.3, 5.1 +/- 3.4, 16.2 +/- 5.4, and 19.0 +/- 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 +/- 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at SO mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.
• Methanesulfonic Acid Catalyzed Friedel–Crafts Reaction of Electron-Rich Arenes with N-Arylmaleimides: A Highly Efficient Metal-Free Route To Access 3-Arylsuccinimides
  作者：Rama Krishna Peddinti、Deepti Gairola

  DOI：10.1055/s-0040-1706008

  日期：2021.6

  Friedel–Crafts reaction is widely used for the C–C bond forming reaction to enable the direct connection of electron-rich arenes to electron-deficient olefins with high regioselectivity. Herein, a highly efficient, metal-free, and environmentally benign F–C strategy of electron-rich arenes with N-arylmaleimides has been developed for the construction of 3-arylsuccinimides in the presence of a green

  Friedel–Crafts反应被广泛用于C–C键形成反应，以使富电子芳烃与具有高区域选择性的缺电子烯烃直接连接。在此，已经开发了一种高效的，无金属且对环境有益的富电子芳烃F-C策略与N-芳基马来酰亚胺，用于在绿色试剂甲磺酸存在下，温和的反应条件下构建3-芳基琥珀酰亚胺。这种高度简便，高产的协议与不同的富电子芳烃具有兼容性。