1-methyl-2,5-dithiocyanato-1H-pyrrole | 18519-17-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-methyl-2,5-dithiocyanato-1H-pyrrole
• 英文别名: (1-methyl-5-thiocyanatopyrrol-2-yl) thiocyanate
• CAS: 18519-17-0
• 化学式: C₇H₅N₃S₂
• 分子量: 195.269
• InChiKey: SUZKSNYCAVLRTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-甲基吡咯 在 sodium perchlorate 作用下， 以 乙腈 为溶剂， 生成 1-methyl-2,5-dithiocyanato-1H-pyrrole
  参考文献：
  名称：

  Double electrooxidative C–H functionalization of (het)arenes with thiocyanate and 4-nitropyrazolate ions

  摘要：

  The double anodic C-H functionalization of N-methyl-1H-pyrrole and N,N-dimethylaniline using both thiocyanate and 4-nitro-1H-pyrazolate ions as nucleophiles has been accomplished for the first time. The mild reaction conditions and considerable pharmacological activity of the target products make such C-S and C-N coupling strategy to be highly attractive for further applications.

  DOI：

  10.1016/j.mencom.2019.05.032

文献信息

• A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions
  作者：Xing Zhang、Chenguang Wang、Hong Jiang、Linhao Sun

  DOI：10.1039/c8ra04407d

  日期：——

  A low-cost and efficient thio- and selenocyanation strategy for electron-rich arenes has been developed under constant-current electrolytic conditions in an undivided cell without the use of any catalyst or oxidant.

  已开发出一种针对富电子芳烃的低成本高效的硫氰化和硒氰化策略，在不使用任何催化剂或氧化剂的情况下，在不分隔电池中的恒定电流电解条件下进行。
• Iodine/MeOH: a novel and efficient reagent system for thiocyanation of aromatics and heteroaromatics
  作者：J.S. Yadav、B.V.S. Reddy、S. Shubashree、K. Sadashiv

  DOI：10.1016/j.tetlet.2004.02.073

  日期：2004.3

  Indoles, pyrroles, oxindoles and aromatic amino compounds undergo smooth thiocyanation with ammonium thiocyanate in the presence of molecular iodine in methanol under mild conditions to afford the corresponding 3-indolyl, 2-pyrrolyl and 4-aryl thiocyanates, respectively, in excellent yields with high selectivity. The reactions proceed rapidly at room temperature without heating or the use of strong

  在甲醇中存在分子碘的条件下，在温和的条件下，在分子碘的存在下，吲哚，吡咯，羟吲哚和芳族氨基化合物与硫氰酸铵进行平滑的硫氰化反应，分别以高收率和优异的收率得到相应的3-吲哚基，2-吡咯基和4-芳基硫氰酸酯。选择性。反应在室温下快速进行，无需加热或使用强路易斯酸。
• NaSCN–(NH4)2Ce(NO3)6 system in heterocycle thiocyanation: synthesis of novel highly potent broad-spectrum fungicides for crop protection
  作者：Mikhail Yu. Sharipov、Igor B. Krylov、Ivan D. Karpov、Olga V. Vasilkova、Anna-Maria V. Oleksiienko、Alexander O. Terent’ev

  DOI：10.1007/s10593-021-02938-y

  日期：2021.5

  A method for thiocyanation of pyrroles, indoles, pyrazolones, and pyrimidine-2,4,6-triones with the NaSCN–(NH4)2Ce(NO3)6 system was proposed. The most important result was the synthesis of dithiocyanated pyrroles with high fungicidal activity against various phytopathogenic fungi.

  提出了一种使用 NaSCN–(NH 4 ) 2 Ce(NO 3 ) 6体系对吡咯、吲哚、吡唑啉酮和嘧啶-2,4,6-三酮进行硫氰化的方法。最重要的结果是合成了对各种植物病原真菌具有高杀菌活性的二硫氰化吡咯。
• Soederbaeck, Acta Chemica Scandinavica (1947), 1954, vol. 8, p. 1851,1855
  作者：Soederbaeck

  DOI：——

  日期：——