5-thiocyanato-2,3-indolinedione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-thiocyanato-2,3-indolinedione
• 英文别名: 5-thiocyanatoisatin；(2,3-dioxo-1H-indol-5-yl) thiocyanate
• 化学式: C₉H₄N₂O₂S
• 分子量: 204.209
• InChiKey: FXJARYYPEZZFQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(1-propylsulfonic)-3-methylimidazolium thiocyanate 、 靛红 在 双氧水 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以81%的产率得到5-thiocyanato-2,3-indolinedione
  参考文献：
  名称：

  使用新型布朗斯台德酸性离子液体对芳香族和杂芳香族化合物进行区域硫代氰化反应。

  摘要：

  描述了一种方便的程序，用于制备1-（1-丙磺酸基）-3-甲基咪唑鎓硫氰酸盐作为新型的布朗斯台德酸性离子液体硫氰化剂和高效的多相催化剂。该催化剂用于在温和的H2O2和EtOH：H2O（1：1 v / v）的氧化剂存在下对吲哚，苯胺，吡咯及其衍生物（芳族和杂芳族有机化合物）进行区域选择性硫氰化。这些反应在温和且简单的条件下进行，从而以高产率和短反应时间提供区域选择性产物。

  DOI：

  10.2174/1386207319666160709191851

文献信息

• Ferric(III) Chloride-Promoted Electrophilic Thiocyanation of Aromatic and Heteroaromatic Compounds
  作者：J. S. Yadav、B. V. Reddy、A. D. Krishna、Ch. Suresh Reddy、A. V. Narsaiah

  DOI：10.1055/s-2005-861852

  日期：——

  Indoles, oxindoles and aromatic amino compounds undergo smooth thiocyanation with ammonium thiocyanate in the presence of anhydrous FeCl 3 in dichloromethane under mild conditions to afford the corresponding 3-indolyl and 4-aryl thiocyanates, respectively, in high yields with excellent selectivity. The use of ferric chloride makes it quite simple, more convenient and practical. This new method offers

  吲哚、羟吲哚和芳族氨基化合物在温和条件下在二氯甲烷中的无水 FeCl 3 存在下与硫氰酸铵进行平滑的硫氰化反应，分别以高产率和优异的选择性得到相应的 3-吲哚基和 4-芳基硫氰酸酯。三氯化铁的使用使其非常简单、方便和实用。这种新方法具有几个优点，例如高转化率、更清洁的反应曲线、短反应时间以及使用廉价且易于获得的催化剂。
• Determination of the promoting effect of nano SiO₂and H₃PO₄@nano SiO₂in the thiocyanation of<i>N</i>-containing aromatic compounds under solvent-free conditions
  作者：Kobra Nikoofar、Samareh Gorji

  DOI：10.1080/17415993.2015.1004066

  日期：2015.3.4

  Silica nanoparticles/ammonium thiocyanate (nano SiO2/NH4SCN) and H3PO4 embedded on nano silica (H3PO4@nano SiO2) in the presence of NH4SCN were found to be effective systems for the thiocyanation of some arylamines and indoles to afford their corresponding thiocyanated adducts at 70 degrees C under solvent-free conditions. The recovery and reusability of nano SiO2 as a prompting system have been investigated. A simple procedure for the synthesis of H3PO4@nano SiO2 has also been represented. In addition, a plausible mechanism of thiocyanation has also been suggested.
• AlCl₃-Promoted Thiocyanation of <i>N</i>-Containing Aromatic and Heteroaromatic Compounds Under Solvent-Free Conditions
  作者：Kobra Nikoofar、Samareh Gorji

  DOI：10.1080/10426507.2014.978321

  日期：2015.7.3

  Aluminum chloride/Ammonium thiocyanate (AlCl3/NH4SCN) was found to be an effective system for the thiocyanation of some arylamines and indoles to afford the corresponding thiocyanated adducts at room temperature under solvent-free conditions. The efficacy of this combined reagent was also examined in the thiocyanation of pyrrole and isatin. A plausible mechanism of thiocyanation has also been suggested.
• Electrochemical thiocyanation of nitrogen-containing aromatic and heteroaromatic compounds
  作者：Lida Fotouhi、Kobra Nikoofar

  DOI：10.1016/j.tetlet.2013.02.106

  日期：2013.6

  An efficient and convenient anodic thiocyanation of nitrogen-containing (hetero)aromatic compounds is described under constant current conditions in the presence of ammonium thiocyanate in methanol at room temperature. We have examined the in situ thiocyanation of various aromatic compounds in the presence of electrochemically generated thiocyanogen at a graphite electrode (the anode) in an undivided cell. (C) 2013 Elsevier Ltd. All rights reserved.