4-cyano-1-methyl-3-methylthio-1H-pyrrole-2,5-dione | 182359-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 4-cyano-1-methyl-3-methylthio-1H-pyrrole-2,5-dione
• 英文别名: 1-methyl-4-(methylsulfanyl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile；1-Methyl-4-methylsulfanyl-2,5-dioxopyrrole-3-carbonitrile
• CAS: 182359-86-0
• 化学式: C₇H₆N₂O₂S
• 分子量: 182.203
• InChiKey: YVTROCVHXRWXAC-UHFFFAOYSA-N

物化性质

• 沸点：
  262.7±40.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-cyano-1-methyl-3-methylthio-1H-pyrrole-2,5-dione 在 劳森试剂 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 9.0h， 生成 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：

  [双(甲硫基)亚甲基]丙烷二腈 在 盐酸 、 sodium hydroxide 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 生成 4-cyano-1-methyl-3-methylthio-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis of Aminopyrimidopyidazines as Chemiluminescent Compounds by Reaction of Functionalized Maleimide with Various Amine Derivatives

  摘要：

  The reaction of ketene dithioacetal, bis(methylthio)methylenepropanedinitrile, with nitromethane gave 2-hydroxyimino-4-cyano-3-methylthiomaleimide (3) which was readily derived to the corresponding 4-cyano-3-methylthiomaleimide (5) by methylation with dimethyl sulfate followed by hydrolysis with hydrochloric acid. Compound 5 smoothly reacted with various amine compounds to give the corresponding amino-polycyclic pyrimidines containing a pyrroline ring, which were readily converted to the desired polycyclic pyridazine derivatives in good yields.

  DOI：

  10.3987/com-96-7499

文献信息

• Syntheses of novel pyridine-based low-molecular-weight luminogens possessing aggregation-induced emission enhancement (AIEE) properties
  作者：Masayori Hagimori、Tatsusada Yoshida、Yasuhisa Nishimura、Yukiko Ogawa、Keitaro Tanaka

  DOI：10.3762/bjoc.18.60

  日期：——

  derivatives 4a–e, which are based on an acceptor–donor–acceptor (A–D–A) system, exhibited aggregation-induced emission enhancement (AIEE) properties in aqueous media. Compounds 4a and 4e, bearing electron-withdrawing groups (Br and CF3, respectively) showed 7.0 and 15 times fluorescence enhancement. Time-dependent density functional theory (TD-DFT) calculations were performed to gain better insight into the

  新型基于吡啶的荧光化合物，即。吡啶并[1,2 - a ]吡咯并[3,4- d ]嘧啶3a、b和N-甲基-4-((pyridin-2-yl)amino)maleimides 4a – e ,通过一锅法选择性制备功能化马来酰亚胺和 2-氨基吡啶在位置 5 处具有给电子或吸电子基团之间的反应，并通过光物理和计算进行了研究。光物理研究表明，所有合成的化合物在有机溶剂中均表现出荧光，而N-甲基-4-((吡啶-2-基)氨基)-取代的马来酰亚胺衍生物4a - e，基于受体-供体-受体（A-D-A）系统，在水性介质中表现出聚集诱导发射增强（AIEE）特性。带有吸电子基团（分别为Br和CF 3 ）的化合物4a和4e显示出7.0和15倍的荧光增强。进行了时间相关的密度泛函理论 (TD-DFT) 计算，以更好地了解具有和不具有 AIEE 特性的化合物的电子性质。
• 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 Thiopyrylocyanines Incorporated Thiopyrano[2,3-b]indole Ring as the Main Constituent
  作者：Yoshinori Tominaga、Yasuhiro Shigemitsu、Shun-ichi Hirayama

  DOI：10.3987/com-02-9612

  日期：——

  The Diels-Alder product, dimethyl 5-methyl-4a-methyl-1-methylthiothiopyrano[4,3-b] indole-3,4-dicarboxylate (2b), which was obtained by the reaction of methyl 1,2-dimethylindole-3 -dithiocarboxylate (1b) with DMAD (dimethyl acetylenedicarboxylate), was easily converted to a 1,5-dimethyl-2,3-bis(methoxycarbonyl)indolo[2,3-b]thiopyrylium perchlorate (5) as the key intermediate for the thiopyrylocyanine and merocyanine dyes. Compounds (5 and 6) were allowed to react with aromatic aldehydes and some electrophilic reagents to yield cyanine and merocyanine dyes (8a-c, 10-12) in good yields.
• Synthesis of Aminopyrimidopyidazines as Chemiluminescent Compounds by Reaction of Functionalized Maleimide with Various Amine Derivatives
  作者：Yoshinori Tominaga、Noriko Yoshioka、Seigo Kataoka

  DOI：10.3987/com-96-7499

  日期：——

  The reaction of ketene dithioacetal, bis(methylthio)methylenepropanedinitrile, with nitromethane gave 2-hydroxyimino-4-cyano-3-methylthiomaleimide (3) which was readily derived to the corresponding 4-cyano-3-methylthiomaleimide (5) by methylation with dimethyl sulfate followed by hydrolysis with hydrochloric acid. Compound 5 smoothly reacted with various amine compounds to give the corresponding amino-polycyclic pyrimidines containing a pyrroline ring, which were readily converted to the desired polycyclic pyridazine derivatives in good yields.