2-chloro-3-p-toluidino-N-p-tolylmaleimide | 307506-88-3

• 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: 2-chloro-3-p-toluidino-N-p-tolylmaleimide
• 英文别名: 3-p-toluidino-2-chloro-N-p-tolylmaleimide；N-tolyl-3-chloro-4-toluidinomaleimide；3-chloro-4-p-toluidino-1-p-tolyl-pyrrole-2,5-dione；3-Chlor-4-p-toluidino-1-p-tolyl-pyrrol-2,5-dion；3-chloro-4-(4-methylanilino)-1-(4-methylphenyl)pyrrole-2,5-dione
• CAS: 307506-88-3
• 化学式: C₁₈H₁₅ClN₂O₂
• 分子量: 326.782
• InChiKey: VISBCDOLIBBOSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-3-p-toluidino-N-p-tolylmaleimide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 以25%的产率得到3-(4-甲基苯胺基)-1-(4-甲基苯基)吡咯-2,5-二酮
  参考文献：
  名称：

  Unexpected chlorine substitution by hydrogen in the reaction of 2-chloro-3-p-toluidino-N-p-tolylmaleimide with DBU: Synthesis and molecular structure of 2-p-toluidino-N-p-tolylmaleimide

  摘要：

  The reaction of p-toluidine with 2,3-dichloromaleic anhydride in the presence of added 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) does not give the known compound 2-chloro-3- p-toluidino-N-p-tolylmaleimide (1), but rather 2-p-toluidino-N-p-tolylmaleimide (2) in low yields. Repeating this same reaction with Et3N, pyridine, tmeda, and 4-Me(2)Npyridine in place of DBU furnishes the expected product 2-chloro-3-p-toluidino-N-p-tolylmaleimide, without the presence of 2-p-toluidino-N-p-tolylmaleimide. The participation of DBU in the chlorine for hydrogen exchange reaction in compound 1 has been demonstrated from the independent thermolysis reaction of 1 with DBU in toluene, where 2 was obtained as the sole isolable product. Compound 2 was isolated and fully characterized in solution, and the molecular structure was established by X-ray diffraction analysis. 2-p-Toluidino-N-p-tolylmaleimide crystallizes in the monoclinic space C2/c, a = 33.630( 5), b = 12.508( 2), c = 7.381( 1), beta = 90.668( 3), V = 3104.3( 8)(3), Z = 8, and D-calc = 1.251 Mg/m(3); R = 0.0357, R-w = 0.0896 for 2011 reflections with I > 2sigma(I).

  DOI：

  10.1023/b:jocc.0000044091.78129.37
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 五氯化磷 作用下， 生成 2-chloro-3-p-toluidino-N-p-tolylmaleimide
  参考文献：
  名称：

  Bischoff; Walden, Justus Liebigs Annalen der Chemie, 1894, vol. 279, p. 123

  摘要：

  DOI：

文献信息

• Color Tuning of the Aggregation-Induced Emission of Maleimide Dyes by Molecular Design and Morphology Control
  作者：Hiroaki Imoto、Kohei Kizaki、Seiji Watase、Kimihiro Matsukawa、Kensuke Naka

  DOI：10.1002/chem.201501519

  日期：2015.8.17

  Aggregation‐induced emission (AIE)‐active maleimide dyes, namely, 2‐p‐toluidino‐N‐p‐tolylmaleimide, 3‐phenyl‐2‐toluidino‐N‐p‐tolylmaleimide, 2‐p‐thiocresyl‐3‐p‐toluidino‐N‐p‐tolylmaleimide, and 2,3‐dithiocresyl‐N‐arylmaleimides, were synthesized by facile synthetic procedures. The dyes show intense emission in the solid state, and emission colors were controlled from green (λmax=527 nm) to orange (λmax=609 nm)

  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
• 3,4-Diaminomaleimide Dyes - Simple Luminophores with Efficient Orange-Red Emission in the Solid State
  作者：Hiroaki Imoto、Ryosuke Fujii、Kensuke Naka

  DOI：10.1002/ejoc.201701479

  日期：2018.2.14

  3,4‐Diaminomaleimides, composed of only C, H, N, and O and minimal aromatic rings, showed efficient orange‐red emission in the solid state. Furthermore, these dyes show aggregation‐induced emission enhancement.

  3,4-二氨基马来酰亚胺仅由C，H，N和O组成，并具有最小的芳环，在固态下显示出有效的橙红色发射。此外，这些染料显示出聚集诱导的发射增强。
• ——
  作者：William H. Watson、Guanmin Wu、Michael G. Richmond

  DOI：10.1023/a:1027498202694

  日期：——

  The reaction of equimolar amounts of p-toluidine with 2,3-dichloromaleic anhydride in refluxing toluene affords 2,3-dichloro-N-p-tolylmaleimide (1) and 2-chloro-3-p-toluidino-N-p-tolylmaleimide (2), as the major and minor products, respectively. While increasing the amount of p-toluidine relative to 2,3-dichloromaleic anhydride yields the latter compound as the major product, the replacement of the chloro group in 2-chloro-3-p-toluidino-N-p-tolylmaleimide by added p-toluidine was not observed in refluxing toluene. Both 1 and 2 were isolated by column chromatography and characterized in solution by IR and NMR spectroscopies. The solid-state structure of 2-chloro-3-p-toluidino-N-p-tolylmaleimide was solved by X-ray crystallography. Further, 2-Chloro-3-p-toluidino-N-p-tolylmaleimide crystallizes in the monoclinic space group C2/c; a = 33.191(8) Angstrom, b = 4.037(1) Angstrom, c = 24.876(6) Angstrom, beta = 107.050(4)degrees, V = 3187(1) Angstrom(3), Z = 8, and d(calc) = 1.362 mg/m(3); R = 0.0561, R-w = 0.1246 for 2087 reflections with I > 2sigma (I).
• Bischoff; Walden, Justus Liebigs Annalen der Chemie, 1894, vol. 279, p. 123
  作者：Bischoff、Walden

  DOI：——

  日期：——
• Unexpected chlorine substitution by hydrogen in the reaction of 2-chloro-3-p-toluidino-N-p-tolylmaleimide with DBU: Synthesis and molecular structure of 2-p-toluidino-N-p-tolylmaleimide
  作者：William H. Watson、Guanmin Wu、Michael G. Richmond

  DOI：10.1023/b:jocc.0000044091.78129.37

  日期：2004.9

  The reaction of p-toluidine with 2,3-dichloromaleic anhydride in the presence of added 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) does not give the known compound 2-chloro-3- p-toluidino-N-p-tolylmaleimide (1), but rather 2-p-toluidino-N-p-tolylmaleimide (2) in low yields. Repeating this same reaction with Et3N, pyridine, tmeda, and 4-Me(2)Npyridine in place of DBU furnishes the expected product 2-chloro-3-p-toluidino-N-p-tolylmaleimide, without the presence of 2-p-toluidino-N-p-tolylmaleimide. The participation of DBU in the chlorine for hydrogen exchange reaction in compound 1 has been demonstrated from the independent thermolysis reaction of 1 with DBU in toluene, where 2 was obtained as the sole isolable product. Compound 2 was isolated and fully characterized in solution, and the molecular structure was established by X-ray diffraction analysis. 2-p-Toluidino-N-p-tolylmaleimide crystallizes in the monoclinic space C2/c, a = 33.630( 5), b = 12.508( 2), c = 7.381( 1), beta = 90.668( 3), V = 3104.3( 8)(3), Z = 8, and D-calc = 1.251 Mg/m(3); R = 0.0357, R-w = 0.0896 for 2011 reflections with I > 2sigma(I).