4-methylsulfanyl-2,5-dioxo-2,5-dihydro-pyrrole-3-carboxylic acid methyl ester | 49601-36-7

• 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: 4-methylsulfanyl-2,5-dioxo-2,5-dihydro-pyrrole-3-carboxylic acid methyl ester
• 英文别名: Methyl 4-methylsulfanyl-2,5-dioxopyrrole-3-carboxylate；methyl 4-methylsulfanyl-2,5-dioxopyrrole-3-carboxylate
• CAS: 49601-36-7
• 化学式: C₇H₇NO₄S
• 分子量: 201.203
• InChiKey: DRUXMLSDIXTROP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-吡啶乙酸甲酯 、 4-methylsulfanyl-2,5-dioxo-2,5-dihydro-pyrrole-3-carboxylic acid methyl ester 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.5h， 以70%的产率得到Methyl 1,3,4-trioxopyrrolo[3,4-b]quinolizine-10-carboxylate
  参考文献：
  名称：

  Synthesis of Fluorescent Pyrrolo[3,4-b]quinolizine Derivatives and Evaluation as a Protein-Labeling Probe

  摘要：

  New fluorescent compounds, pyrrolo[3,4-b]quinolizines, were synthesized in good yields via a one-pot method based on the condensation of functionalized maleimides (1 a c) with 2-pyridylacetonitrile (2a), and alkyl 2-pyridylacetates (2b, c). These pyrrolo[3,4-b]quinolizine derivatives emitted over a wide wavelength range in solution (Em max: 484-604 nm) and in the solid state (Em max: 534-640 nm). In addition, we evaluated the utility of these heterocycles as fluorescent labeling probes for BSA.

  DOI：

  10.3987/com-11-12285

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.
• Synthesis of Fluorescent Pyrrolo[3,4-b]quinolizine Derivatives and Evaluation as a Protein-Labeling Probe
  作者：Yoshinori Tominaga、Masayori Hagimori、Naoko Mizuyama、Kenichirou Yokota、Osamu Morinaga、Yasuchika Yamaguchi、Hideo Saji

  DOI：10.3987/com-11-12285

  日期：——

  New fluorescent compounds, pyrrolo[3,4-b]quinolizines, were synthesized in good yields via a one-pot method based on the condensation of functionalized maleimides (1 a c) with 2-pyridylacetonitrile (2a), and alkyl 2-pyridylacetates (2b, c). These pyrrolo[3,4-b]quinolizine derivatives emitted over a wide wavelength range in solution (Em max: 484-604 nm) and in the solid state (Em max: 534-640 nm). In addition, we evaluated the utility of these heterocycles as fluorescent labeling probes for BSA.