3-(4-甲基苯胺基)-1-(4-甲基苯基)吡咯-2,5-二酮 | 53683-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 中文名称: 3-(4-甲基苯胺基)-1-(4-甲基苯基)吡咯-2,5-二酮
• 英文名称: 2-p-toluidino-N-p-tolylmaleimide
• 英文别名: 3-p-toluidino-N-p-tolylmaleimide；N-tolyl-3-toluidino-maleimide；3-(4-methyl-anilino)-1-p-tolyl-pyrrole-2,5-dione；3-p-toluidino-1-p-tolyl-pyrrole-2,5-dione；3-p-Toluidino-1-p-tolyl-pyrrol-2,5-dion；1H-Pyrrole-2,5-dione, 1-(4-methylphenyl)-3-[(4-methylphenyl)amino]-；3-(4-methylanilino)-1-(4-methylphenyl)pyrrole-2,5-dione
• CAS: 53683-82-2
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: BILJFGMLQJRWBP-UHFFFAOYSA-N

物化性质

• 熔点：
  229 °C
• 沸点：
  462.0±45.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 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：

  3-(4-甲基苯胺基)-1-(4-甲基苯基)吡咯-2,5-二酮 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以13%的产率得到2-thioxo-1-(p-tolyl)-3-(p-tolylamino)-2,5H-dihydropyrrol-5-one
  参考文献：
  名称：

  Die schwefelung c-substituierter maleinimide

  摘要：

  DOI：

  10.1016/s0040-4020(01)91501-7
• 作为产物：
  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

文献信息

• Transition metal free K2CO3 mediated thioarylation, selenoarylation and arylation of 2-aminomaleimides at ambient temperature
  作者：Mohit Saroha、Gaurav Bartwal、Jitender M. Khurana

  DOI：10.1016/j.tet.2019.130486

  日期：2019.9

  Transition metal free thioarylation, selenoarylation and arylation of 2-aminomaleimide, using thiophenols, diaryl diselenides and arylhydrazine hydrochlorides respectively, has been reported in DMSO under aerobic condition in presence of K2CO3 at room temperature. The reaction occurs smoothly without prerequisite N-protection of 2-aminomaleimide. The synthesis of novel, polyfunctionalized maleimides

  已经报道了在DMSO中在有氧条件下在室温下在室温下存在K 2 CO 3的情况下分别使用硫酚，二芳基二硒化物和芳基肼盐酸盐的过渡金属游离的硫代芳基化，2-氨基马来酰亚胺的芳基化和芳基化。该反应平稳进行而没有先决条件的2-氨基马来酰亚胺的N-保护。新型，多官能化的马来酰亚胺的合成已通过烯胺的直接C–H活化而实现。Thioarylation和selenoarylation提出要继续经由二硫化物/ diselenides和芳基化已提议将继续经由芳自由基。
• Arylaminomaleimides as a New Class of Aggregation-induced Emission-active Molecules Obtained from Organoarsenic Compounds
  作者：Takuji Kato、Kensuke Naka

  DOI：10.1246/cl.2012.1445

  日期：2012.11.5

  Heating 1,4-dihydro-1,4-diarsininetetracarboxylic acid dianhydride with excess amounts of aniline and toluidine provided 3-anilino-N-phenylmaleimide and 3-p-toluidino-N-p-tolylmaleimide, respectively, which showed aggregation-induced emission (AIE) properties. Not only are the present aminomaleimide derivatives simple-structured AIE-active molecules, but they also exhibit pH responsive properties without introducing additional functional units.

  将1,4-二氢-1,4-二砷酸四羧酸二酸酐与过量的苯胺和甲苯胺加热，分别得到3-苯基氨基美克霉素和3-对甲苯氨基-N-对甲苯美克霉素，它们显示出聚集诱导发光（AIE）特性。这些氨基美克霉素衍生物不仅是结构简单的AIE活性分子，而且在不引入额外功能单元的情况下，还表现出pH响应特性。
• Reaction of Ambident Dianions with Oxalic Acid Dielectrophiles – Effect of the Heteroatoms of the Dinucleophile on the Regiochemistry of Cyclization
  作者：Peter Langer、Jörg Wuckelt、Manfred Döring、Rainer Beckert

  DOI：10.1002/(sici)1099-0690(199807)1998:7<1467::aid-ejoc1467>3.0.co;2-h

  日期：1998.7

  Y-Shaped ambident dianions 1-6 were reacted with dielectrophilic oxalic acid-bis(imidoyl)dichlorides 7 providing a convenient access to novel N-heterocycles 8-13 containing a heteroanalogous oxalic acid unit. The cyclization reactions generally proceeded with good regioselectivity which is controlled by the heteroatoms of the dianion reagents.

  使Y形的环境双价金属1-6与介电的草酸-双（亚氨基酰基）二氯化物7反应，从而提供了方便地进入含有杂类似草酸单元的新型N-杂环8-13的途径。环化反应通常以良好的区域选择性进行，该区域选择性由二价阴离子试剂的杂原子控制。
• 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。