methyl 1-methyl-4-methylthio-2,5-dioxo-3-pyrroline-3-carboxylate | 187842-60-0

• 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: methyl 1-methyl-4-methylthio-2,5-dioxo-3-pyrroline-3-carboxylate
• 英文别名: Methyl 1-methyl-4-methylsulfanyl-2,5-dioxopyrrole-3-carboxylate
• CAS: 187842-60-0
• 化学式: C₈H₉NO₄S
• 分子量: 215.23
• InChiKey: AKSLZIZGGDXYIO-UHFFFAOYSA-N

物化性质

• 沸点：
  317.2±42.0 °C(predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 1-methyl-4-methylthio-2,5-dioxo-3-pyrroline-3-carboxylate 以 甲醇 、 二苯醚 为溶剂， 反应 1.5h， 生成 4-Hydroxy-3,6-dimethyl-1-phenyl-1H-pyrazolo[3,4-b]pyrrolo[3,4-e]pyridine-5,7-dione
  参考文献：
  名称：

  Synthesis and Chemiluminescence of 1,3-Disubstituted 4-Hydroxypyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones

  摘要：

  Reactions of 1,3-disubstituted 5-aminopyrazole-4-carboxylate derivatives (la-c) with dimethyl acetylenedicarboxylate gave the corresponding dimethyl 1,3-disubstituted 4-hydroxypyrazolo[3,4-b]pyridine-5,6-dicarboxylates (2a-c) which reacted with hydrazine hydrate to give 1,3-disubstituted 4-hydroxy-1H-pyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones (3a-d). These tricyclic pyridazine derivatives were alternatively synthesized from 4-hydroxypyrrolo[3,4-e] pyrazolo[3,4-b]pyridine-5,7-diones (7a-c) prepared by reactions of 5-aminopyrazoles (1e-g) with 1-methyl-3-methylthio-4-methoxycarbonylmaleimide (5) followed by Gould-Jacacobs reaction. These tricyclic pyridazine derivatives were evaluated for chemiluminescence. 4-Hydroxy-3-methylthio-1-phenyl-1H-pyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-dione (3d) showed the greatest chemiluminescence intensity in the presence of H2O2 and peroxidase in a solution of phosphate buffer at pH 10.

  DOI：

  10.3987/com-96-s17
• 作为产物：
  描述：

  methyl 2-methoxyimino-3-methylthio-5-oxopyrroline-4-carboxylate 在 盐酸 作用下， 以67%的产率得到methyl 1-methyl-4-methylthio-2,5-dioxo-3-pyrroline-3-carboxylate
  参考文献：
  名称：

  Synthesis and Chemiluminescence of 1,3-Disubstituted 4-Hydroxypyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones

  摘要：

  Reactions of 1,3-disubstituted 5-aminopyrazole-4-carboxylate derivatives (la-c) with dimethyl acetylenedicarboxylate gave the corresponding dimethyl 1,3-disubstituted 4-hydroxypyrazolo[3,4-b]pyridine-5,6-dicarboxylates (2a-c) which reacted with hydrazine hydrate to give 1,3-disubstituted 4-hydroxy-1H-pyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones (3a-d). These tricyclic pyridazine derivatives were alternatively synthesized from 4-hydroxypyrrolo[3,4-e] pyrazolo[3,4-b]pyridine-5,7-diones (7a-c) prepared by reactions of 5-aminopyrazoles (1e-g) with 1-methyl-3-methylthio-4-methoxycarbonylmaleimide (5) followed by Gould-Jacacobs reaction. These tricyclic pyridazine derivatives were evaluated for chemiluminescence. 4-Hydroxy-3-methylthio-1-phenyl-1H-pyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-dione (3d) showed the greatest chemiluminescence intensity in the presence of H2O2 and peroxidase in a solution of phosphate buffer at pH 10.

  DOI：

  10.3987/com-96-s17

文献信息

• Absorption and fluorescence spectra of new pyrrolo[3,4‐<i>b</i>]quinolizines in condensed phases: A joint experimental and computational study
  作者：Yasuhiro Shigemitsu、Yasuhisa Nishimura、Masayori Hagimori

  DOI：10.1002/jhet.4708

  日期：2023.10

  the electronic and fluorescence spectra in solution as well as in solid state. The solvent effects on the absorption and emission spectra were theoretically investigated by the snapshots-averaged spectra obtained by the first principle molecular dynamics combined with polarizable continuum model (PCM). Alternatively, the solute–solvent interaction effect on the spectra was examined by fragment molecular

  新合成的吡咯并[3,4 -b]喹嗪、溶液中的蓝绿至橙红色荧光染料和固态中的黄色至红色荧光染料，通过实验和计算研究了溶液中和固态中的电子和荧光光谱。通过第一原理分子动力学结合可极化连续介质模型（PCM）获得的快照平均光谱，从理论上研究了溶剂对吸收和发射光谱的影响。或者，通过片段分子轨道时间相关密度泛函理论（FMO-TDDFT）检查溶质-溶剂相互作用对光谱的影响，该理论考虑了明确的溶质-溶剂相互作用。结果表明，FMO-TDDFT 正确再现了 PCM 的定量预测局限性以及二氯甲烷和乙醇中的溶剂化显色位移。通过以下方法在激发态势面上分析了化合物的发光量子产率S 0 / S 1 -圆锥形交叉点。
• 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.
• 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 and Chemiluminescence of 10-Hydroxy- and 10-Aminopyridazino[4,5-b]quinoline-1,4(2H,3H)-diones
  作者：Yoshinori Tominaga、Noriko Yoshioka、Seigo Kataoka、Yasuhiro Shigemitsu、Takashi Hirota、Kenji Sasaki

  DOI：10.3987/com-98-s(h)20

  日期：——

  Substituted anilines reacted with methyl 1-methyl-4-methyrthio-2,5-dioxo-3-pyrroline-3-carboxylate (1) in refluxing methanol to give the corresponding methyl 1-methyl-2,5-dioxo-4-phenylamino-3-pyrroline-3-carboxylates (3a-e) which were converted in good yields to 2-methylpyrrolo[3,4-b]quinoline derivatives (4a-e) by heating in diphenyl ether. Reaction of 4a-e with hydrazine hydrate gave 10-hydroxypyridazino[4,5-b]quinoline-1,4(2H,3H)-diones (5a-e) in good yields. The desired 10-aminopyridazino[4,5-b]quinoline-1,4(2H, 3H)-diones (8a-e) were obtained by the chlorination of 4a-e with phosphorus oxychloride followed by ammonolysis with 28% ammonium hydroxide in good yields. Compounds (5) and (8) were found to be efficiently chemiluminescent in a similarly to luminol in the presence of H2O2 and horseradish peroxidase in a solution of a phosphate buffer pH 8.0.