3-Cyano-4-(4-N,N-diethylamino)phenyl-1-methyl-1H-pyrrole-2,5-dione

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-Cyano-4-(4-N,N-diethylamino)phenyl-1-methyl-1H-pyrrole-2,5-dione
• 英文别名: 4-[4-(Diethylamino)phenyl]-1-methyl-2,5-dioxopyrrole-3-carbonitrile；4-[4-(diethylamino)phenyl]-1-methyl-2,5-dioxopyrrole-3-carbonitrile
• 化学式: C₁₆H₁₇N₃O₂
• 分子量: 283.33
• InChiKey: BBMMSJAUSNYOFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Cyano-4-(4-N,N-diethylamino)phenyl-1-methyl-1H-pyrrole-2,5-dione 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以50%的产率得到3-Cyano-4-(4-N,N-diethylamino)phenyl-1-methyl-5-oxo-1H-pyrrole-2-thione
  参考文献：
  名称：

  Synthesis of New Methine Class of Dyes Bearing Maleimide Ring System

  摘要：

  Reaction of 1-methyl-3-methylthiomaleimides (1a-c) with N,N-dialkylanilines (2) under refluxing in acetic acid condition gave the corresponding 3-(4-diakylamino)phenyl-1-methylmaleimides (3a-g). Treatment of these 1-methyl-3-phenylmaleimides (3a, c) with Lawesson's reagent under refluxing in toluene afforded new blue dyes, 4-(4-dialkylamino)phenyl-3-cyano-1-methyl-5-oxopyrrole-2-thiones (5a, b) which are brilliant blue dyes appearing at 606 and 615 nm (log epsilon: 4.59 and 4.50) in UV spectra. Reaction of 4-methoxycarbonyl-1-methyl-3 -methylthiomaleimide (1b) with 3-dialkylaminophenol under the same reaction conditions gave cyclized products, 2H, 4H-[1]-benzopyrano[3,4-c]pyrrole-1,3,4-triones (6a-c) in good yields.

  DOI：

  10.3987/com-97-s12
• 作为产物：
  描述：

  N,N-二乙基苯胺 、 4-cyano-1-methyl-3-methylthio-1H-pyrrole-2,5-dione 以 溶剂黄146 为溶剂， 反应 9.0h， 以53%的产率得到3-Cyano-4-(4-N,N-diethylamino)phenyl-1-methyl-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis of New Methine Class of Dyes Bearing Maleimide Ring System

  摘要：

  Reaction of 1-methyl-3-methylthiomaleimides (1a-c) with N,N-dialkylanilines (2) under refluxing in acetic acid condition gave the corresponding 3-(4-diakylamino)phenyl-1-methylmaleimides (3a-g). Treatment of these 1-methyl-3-phenylmaleimides (3a, c) with Lawesson's reagent under refluxing in toluene afforded new blue dyes, 4-(4-dialkylamino)phenyl-3-cyano-1-methyl-5-oxopyrrole-2-thiones (5a, b) which are brilliant blue dyes appearing at 606 and 615 nm (log epsilon: 4.59 and 4.50) in UV spectra. Reaction of 4-methoxycarbonyl-1-methyl-3 -methylthiomaleimide (1b) with 3-dialkylaminophenol under the same reaction conditions gave cyclized products, 2H, 4H-[1]-benzopyrano[3,4-c]pyrrole-1,3,4-triones (6a-c) in good yields.

  DOI：

  10.3987/com-97-s12

文献信息

• Synthesis of New Methine Class of Dyes Bearing Maleimide Ring System
  作者：Yoshinori Tominaga、Kaori Komiya、Sachiko Itonaga、Noriko Yoshioka、Seigo Kataoka、Kenji Sasaki、Takashi Hirota

  DOI：10.3987/com-97-s12

  日期：——

  Reaction of 1-methyl-3-methylthiomaleimides (1a-c) with N,N-dialkylanilines (2) under refluxing in acetic acid condition gave the corresponding 3-(4-diakylamino)phenyl-1-methylmaleimides (3a-g). Treatment of these 1-methyl-3-phenylmaleimides (3a, c) with Lawesson's reagent under refluxing in toluene afforded new blue dyes, 4-(4-dialkylamino)phenyl-3-cyano-1-methyl-5-oxopyrrole-2-thiones (5a, b) which are brilliant blue dyes appearing at 606 and 615 nm (log epsilon: 4.59 and 4.50) in UV spectra. Reaction of 4-methoxycarbonyl-1-methyl-3 -methylthiomaleimide (1b) with 3-dialkylaminophenol under the same reaction conditions gave cyclized products, 2H, 4H-[1]-benzopyrano[3,4-c]pyrrole-1,3,4-triones (6a-c) in good yields.