1-(4-(methylthio)phenyl)-1H-pyrrole-2,5-dione | 54669-29-3

• 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-(4-(methylthio)phenyl)-1H-pyrrole-2,5-dione
• 英文别名: N-(4'-Methylthiophenyl)-maleimid；N-(4'-methylthiophenyl)maleimide；1-(4-Methylsulfanylphenyl)pyrrole-2,5-dione
• CAS: 54669-29-3
• 化学式: C₁₁H₉NO₂S
• mdl: MFCD00175125
• 分子量: 219.264
• InChiKey: IUJIKENGDDWJCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 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：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  四氢呋喃 、 1-(4-(methylthio)phenyl)-1H-pyrrole-2,5-dione 在 三乙烯二胺 、 氧气 作用下， 以 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以67 %的产率得到(E)-3-(dihydrofuran-2(3H)-ylidene)-1-(4-(methylthio)phenyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  电子供体-受体复合物实现环醚环外烯基化过程中的可见光诱导氢原子转移

  摘要：

  开发了一种电子供体-受体（EDA）触发的氢原子转移（HAT）工艺，用于从环醚有效生成α-烷氧基自由基，以合成具有独特E选择性的环外烯基化醚。明智选择的供体-受体对（DABCO 和马来酰亚胺）在可见光照射下充当所需的 HAT 试剂，无需使用任何光催化剂或过氧化物。探索了多种底物以证明这种交叉脱氢转化的多种适用性和实际可行性。详细的机理研究揭示了氧化环境下的自由基反应途径。

  DOI：

  10.1021/acs.orglett.3c03099
• 作为产物：
  描述：

  4-氨基茴香硫醚 在 sodium acetate 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(4-(methylthio)phenyl)-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

• 萘醌多并环衍生物及其制备方法及其用途
  申请人：西华大学

  公开号：CN113717182B

  公开（公告）日：2022-11-29

  本发明涉及药物化学技术领域，公开了萘醌多并环衍生物及其制备方法及其用途。所述萘醌多并环衍生物的结构通式如式I所示：R1为Ph‑、Br‑、OH‑、H‑；R2为‑OMe、Me‑、‑CN、‑NO2、F‑、Cl‑、Br‑、H‑、‑COOH；R3为烷基、烯烃基、苄基，烷基的碳原子个数为1～4，烯烃基的碳原子个数为3～4；R4＝R5＝烷基或取代烷基，芳基，取代芳基，杂芳基，烷基的碳原子个数为1～6；或者R4为环己基；R5为H、苯基。本申请制备得到的萘醌多并环衍生物，具有一定的生物活性，可作为潜在药物或候选药物分子用于抗癌、抗肿瘤、抗炎、抗菌等方面的研究，同时具有良好的光物理性质，可应用于荧光材料领域。
• Copper-catalyzed direct oxidative amination of maleimides and quinones with formamides in the presence of an oxidant KIO3
  作者：Yu Dong、Zhen-Zhen Peng、Lin Chen、Yue-Qin Lin、Mei-Feng Lan、Chun-Mei Wu、Zhi-Chuan Shi、Guowei Deng、Bing He

  DOI：10.1016/j.tet.2024.133916

  日期：2024.4

  A facile, efficient, and practical method for copper-catalyzed direct amination of maleimides and quinones with formamides in the presence of an oxidant KIO has been developed. It allows a facile access to a wide range of functionalized molecules with privileged scaffolds in drugs and natural products such as maleimides and quinones. A variety of substituted 3-amino-maleimides and 2-amino-quinones

  开发了一种在氧化剂 KIO 存在下铜催化马来酰亚胺和醌与甲酰胺直接胺化的简便、高效且实用的方法。它可以轻松获得各种功能化分子，并在药物和天然产物（如马来酰亚胺和醌）中具有特殊的支架。合成了多种取代的3-氨基马来酰亚胺和2-氨基醌，产率中等至优异。
• US3985894A
  申请人：——

  公开号：US3985894A

  公开（公告）日：1976-10-12
• 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.
• Visible-Light-Induced Hydrogen Atom Transfer En Route to Exocylic Alkenylation of Cyclic Ethers Enabled by Electron Donor–Acceptor Complex
  作者：Tanumoy Mandal、Sanju Das、Rohan Maji、Suman De Sarkar

  DOI：10.1021/acs.orglett.3c03099

  日期：2023.10.27

  An electron donor–acceptor (EDA)-triggered hydrogen atom transfer (HAT) process is developed for the efficient generation of an α-alkoxy radical from cyclic ethers to synthesize exocyclic alkenylated ethers with exclusive E-selectivity. A judiciously chosen donor–acceptor pair (DABCO and maleimide) serves as the desired HAT reagent under visible light irradiation without using any photocatalyst or

  开发了一种电子供体-受体（EDA）触发的氢原子转移（HAT）工艺，用于从环醚有效生成α-烷氧基自由基，以合成具有独特E选择性的环外烯基化醚。明智选择的供体-受体对（DABCO 和马来酰亚胺）在可见光照射下充当所需的 HAT 试剂，无需使用任何光催化剂或过氧化物。探索了多种底物以证明这种交叉脱氢转化的多种适用性和实际可行性。详细的机理研究揭示了氧化环境下的自由基反应途径。