2,3-dichloro-N-(4-methoxyphenyl)maleimide | 34379-53-8

• 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: 2,3-dichloro-N-(4-methoxyphenyl)maleimide
• 英文别名: 2,3-dichloro-N-(p-methoxyphenyl)maleimide；N-(4-methoxyphenyl)-3,4-dichloromaleimide；2,3-dichloro-N-p-anisoylmaleimide；3,4-dichloro-1-(4-methoxy-phenyl)-pyrrole-2,5-dione；3,4-Dichloro-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dione；3,4-dichloro-1-(4-methoxyphenyl)pyrrole-2,5-dione
• CAS: 34379-53-8
• 化学式: C₁₁H₇Cl₂NO₃
• 分子量: 272.087
• InChiKey: YVTFIECPUFOBMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 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：

  2,3-dichloro-N-(4-methoxyphenyl)maleimide 在 sodium azide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 2-(4-methoxy-phenyl)-6-methyl-pyrrolo[3,4-b]quinoxaline-1,3-dione
  参考文献：
  名称：

  Generality and Scope of the Synthesis of 2-Arylpyrrolo[3,4-b]quinoxaline-1,3-diones from 2,3-Dichloro-N-arylmaleimides. II

  摘要：

  Nucleophilic substitution of 2,3-dichloro-N-arylmaleimides (1) and (2) with a series of arylamines gives 2-arylamino-3-chloro-N-arylmaleimides (3) and (4), respectively. When 4 is treated with sodium azide at room temperature, it cyclizes to the 2-(p-methoxyphenyl)pyrrolo[3,4-b]quinoxaline-1,3-diones (5). Under the same conditions, the 2-(p-nitrophenyl) analogue (3) fails to cyclize. Ring closure is also subject to the steric and electronic effects of substituents in the nucleophile.

  DOI：

  10.3987/com-99-8716
• 作为产物：
  描述：

  2,3-二氯马来酸酐 、 甲氧苯胺 以 甲苯 为溶剂， 反应 4.0h， 以77%的产率得到2,3-dichloro-N-(4-methoxyphenyl)maleimide
  参考文献：
  名称：

  分子设计和形态学控制对马来酰亚胺染料聚集诱导发射的颜色调节

  摘要：

  聚集诱导发光（AIE）-active马来酰亚胺染料，即，2- p -toluidino- ñ - p -tolylmaleimide，3-苯基-2- toluidino- Ñ - p -tolylmaleimide，2- p -thiocresyl -3- p - toluidino- ñ - p -tolylmaleimide和2,3- dithiocresyl- ñ -arylmaleimides，通过简便的合成方法合成。染料显示出在固体状态下强发射，以及发光颜色从绿色控制（λ最大= 527纳米）到橙色（λ最大通过改变马来酰亚胺的2位和3位上的取代基以及固态堆积结构来改变= 609 nm）。2,3-二取代的马来酰亚胺染料有效地经历了其发射波长的红移。此外，一些染料表现出机械变色和多态性，并且它们的发射性质显着取决于固体样品的形态。通过X射线衍射研究了发射行为的机理。马来酰亚胺环上氮原子

  DOI：

  10.1002/chem.201501519

文献信息

• Synthesis and Biological Evaluation of 3-Chloro-4-(indol-3-yl)-2,5- pyrroledione Derivatives as Antitumor Agents
  作者：Yuchen Lin、Jing Chen

  DOI：10.2174/1570180811310050003

  日期：2013.4.1

  A series of 3-chloro-4-(indol-3-yl)-2,5-pyrroledione derivatives were synthesized and evaluated for their cytotoxic activities in vitro against five human cancer cell lines (K562, A549, ECA-109, KB and SMMC-7721). Most compounds displayed potent cytotoxicity with IC50 values in low micromolar range. The results showed that the existence of the chlorine atom at 3-position on the pyrroledione ring was crucial for the activity. Compound 6a, the most potent one (IC50: 0.67∼3.93 μM), would be a promising template for further development of novel antitumor agents

  合成了一系列3-氯-4-(吲哚-3-基)-2,5-吡咯二酮衍生物，并评估其对五种人癌细胞系（K562、A549、ECA-109、KB和SMMC-7721）的体外细胞毒性活性。大多数化合物表现出强效的细胞毒性，IC50值在低微摩尔范围内。结果表明，吡咯二酮环上3位的氯原子的存在对活性至关重要。化合物6a是最有效的（IC50：0.67∼3.93 μM），将成为进一步开发新型抗肿瘤药物的有前景的模板。
• Synthesis and Spectral Properties of Fluorescent Dithienylmaleimides
  作者：Valerii Z. Shirinian、Mikhail M. Krayushkin、Boris V. Nabatov、Ol’ga Yu. Kuznetsova、Alexey A. Shimkin

  DOI：10.1246/bcsj.79.889

  日期：2006.6

  A convenient preparative method of the synthesis of dithienylethenes based on maleimides was proposed. Previously, difficult accessible dithienylethene derivatives, in which 2-thienyl substituents are attached to the double bond of maleimide, have been synthesized. The spectral properties of the dithienylmaleimides were studied and it has been shown that these compounds do not belong to photochromes but they possess fluorescent properties.

  提出了一种基于马来酰亚胺的二噻吩乙烯合成便捷制备方法。此前，人们已经合成了难以获得的二噻吩乙烯衍生物，其中2-噻吩基取代基连接在马来酰亚胺的双键上。对二噻吩马来酰亚胺的光谱特性进行了研究，结果表明这些化合物不属于光致变色体，但具有荧光特性。
• Synthesis, redox properties, and X-ray diffraction structure of 2,3-bis(ethylthio)-N-(p-MeOC6H4)maleimide
  作者：William H. Watson、Tao Chen、Michael G. Richmond

  DOI：10.1007/s10870-004-7652-1

  日期：2004.11

  Refluxing 2,3-dichloromaleic anhydride with p-anisidine in benzene with water removal gives the condensation product 2,3-dichloro-N-(p-MeOC6H4)maleimide (1) 75% yield. This new maleimide compound reacts with added ethanethiol in the presence of Et3N or DBU to furnish the bidentate sulfide ligand 2,3-bis(ethylthio)-N-(p-MeOC6H4)maleimide (2) in 85% yield. Each product has been characterized in solution by IR, NMR, and UV-vis spectroscopies, and the solid-state structure of 2,3-bis(ethylthio)-N-(p-MeOC6H4)maleimide was unequivocally established by single-crystal X-ray diffraction analysis. 2,3-bis(Ethylthio)-N-(p-MeOC6H4)maleimide crystallizes in the monoclinic space group C2/c, a = 20.035(3)Å, b = 9.188(1)Å, c = 16.887(2)Å, β = 93.696(2)°, V = 3102.3(8)Å3, Z = 8, and Dcalcd = 1.385 mg/m3; R = 0.0268, Rw = 0.0676 for 2025 reflections with I > 2σ (I). The nature of the LUMO in 2,3-bis(ethylthio)-N-(p-MeOC6H4)maleimide (2) has been determined by extended Hückel molecular orbital calculations, and these data are discussed relative to the cyclic voltammetry results and other structurally relevant compounds prepared in our labs.

  将 2,3-二氯马来酸酐与对甲氧基苯胺在苯中回流，除去水，得到缩合产物 2,3-二氯-N-(p-MeOC6H4)马来酰亚胺（1），收率为 75%。这种新的马来酰亚胺化合物在 Et3N 或 DBU 存在下与添加的乙硫醇反应，生成双齿硫化物配体 2,3-双（乙硫基）-N-(p-MeOC6H4)马来酰亚胺（2），收率为 85%。通过红外光谱、核磁共振和紫外-可见光谱对溶液中的每种产物进行了表征，并通过单晶 X 射线衍射分析明确确定了 2,3-双（乙硫基）-N-(p-MeOC6H4)马来酰亚胺的固态结构。2,3-双（乙硫基）-N-(对-MeOC6H4)马来酰亚胺在单斜空间群 C2/c 中结晶，a = 20.035(3)埃，b = 9.188(1)埃，c = 16.887(2)Å, β = 93.696(2)°, V = 3102.3(8)Å3, Z = 8, and Dcalcd = 1.385 mg/m3; R = 0.0268, Rw = 0.0676 for 2025 reflections with I > 2σ (I).通过扩展 Hückel 分子轨道计算，确定了 2,3-双（乙硫基）-N-(p-MeOC6H4)马来酰亚胺 (2) 中 LUMO 的性质，并结合循环伏安法结果和我们实验室制备的其他结构相关化合物对这些数据进行了讨论。
• REPELLENT AGAINST AQUATIC ORGANISMS
  申请人：IHARA CHEMICAL INDUSTRY Co., Ltd.

  公开号：EP0010107A1

  公开（公告）日：1980-04-30

  A repellent against aquatic organisms, characterized by comprising as effective ingredients at least one compound of N-arylmaleimide represented by the general formula: Wherein: X, and X2 are the same or different, and denote hydrogen and halogen atoms, respectively; Y is a halogen atom, alkyl group or lower alkoxy group; and n is 0 or an interger from 1 to 3; and at least one compound selected from a group of organotin compounds comprising bis (tri-n-butyl tin) mesodibromosuccinate, tripenyl tin monochloroacetate, triphenyl tin hydroxide and bis (tri-n-butyl tin) oxide.

  一种针对水生生物的驱避剂，其特征在于作为有效成分包含至少一种由通式表示的 N-芳基马来酰亚胺化合物： 其中：X 和 X2 是相同或不同的，分别表示氢原子和卤素原子；Y 是卤素原子、烷基或低级烷氧基；n 是 0 或 1 至 3 的中间值；以及至少一种选自有机锡化合物组的化合物，该组有机锡化合物包括双（三正丁基锡）间二溴琥珀酸酯、三烯基锡一氯乙酸酯、三苯基氢氧化锡和双(三正丁基锡)氧化物。
• Hansen, Thomas K.; Varma, Sukumar K.; Edge, Stephen, Journal of the Chemical Society. Perkin transactions I, 1992, # 14, p. 1807 - 1810
  作者：Hansen, Thomas K.、Varma, Sukumar K.、Edge, Stephen、Charlton, Adam、Underhill, Allan E.、Becher, Jan

  DOI：——

  日期：——