3-thiocyanato-1H-indole-5-carbonitrile | 1044513-31-6

• 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: 3-thiocyanato-1H-indole-5-carbonitrile
• 英文别名: 5-cyano-3-thiocyanato-1H-indole；(5-cyano-1H-indol-3-yl) thiocyanate
• CAS: 1044513-31-6
• 化学式: C₁₀H₅N₃S
• 分子量: 199.236
• InChiKey: PAJMDFNJOBXIAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：
  88.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-thiocyanato-1H-indole-5-carbonitrile 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and evaluation of benzimidazole carbamates bearing indole moieties for antiproliferative and antitubulin activities

  摘要：

  A series of novel benzimidazole carbamates bearing indole moieties with sulphur or selenium atoms connecting the aromatic rings were synthesised and evaluated for their antiproliferative activities against three human cancer cell lines (SGC-7901. A-549 and HT-1080) using an MTT assay. Compounds 10a, 10b, 7a, 7b and 7f showed significant activities against these cell lines. The most potent compound in this series, 10a, was selected to investigate its antitumour mechanism. In addition, molecular docking studies suggested that compound 10a interacts very closely with the nocodazole docking pose through hydrogen bonds at the colchicine binding site of tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.071
• 作为产物：
  描述：

  5-氰基吲哚 、 potassium thioacyanate 在 Graphene oxide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以48%的产率得到3-thiocyanato-1H-indole-5-carbonitrile
  参考文献：
  名称：

  Visible-Light-Induced, Graphene Oxide-Promoted C3-Chalcogenylation of Indoles Strategy under Transition-Metal-Free Conditions

  摘要：

  已实现在室温下利用可见光辐照和氧化石墨烯作为促进剂合成3-硫基吲哚和3-硒基吲哚的高效通用方法。该反应具有高产率、简单操作、无金属和无碘条件、易处理的氧化剂以及可扩展至克级合成的特点。这一简单的方案使得可以获得广泛的3-芳基硫基吲哚、3-芳基硒基吲哚，甚至3-硫氰基吲哚，产率良好至优良。

  DOI：

  10.3390/molecules27030772

文献信息

• A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles employing CeCl₃·7H₂O in PEG-400
  作者：Margiani P. Fortes、Mariana M. Bassaco、Teodoro S. Kaufman、Claudio C. Silveira

  DOI：10.1039/c4ra05625f

  日期：——

  efficient and eco-friendly promoter system for the convenient synthesis of 5-sulfenyl tetrazoles derived from indoles and pyrroles, is reported. The synthesis entails the [3 + 2] cycloaddition reaction of NaN3 with 3-thiocyanato indoles (including 3,3′-di-thiocyanato-1H,1H′,2,2′-biindoles) and 2-thiocyanato pyrroles. The thiocyanates were conveniently obtained by the oxone-mediated thiocyanation of differently

  据报道，在聚乙二醇400（PEG-400）中使用CeCl 3 ·7H 2 O作为有效和环保的促进剂体系，可方便地合成由吲哚和吡咯衍生的5-亚磺酰基四唑。合成需要使NaN 3与3-硫代氰基吲哚（包括3,3'-二硫代氰基-1 H，1 H '，2,2'-双吲哚）和2-硫代氰基吡咯进行[3 + 2]环加成反应。硫氰酸盐可通过不同取代的起始吲哚，1 H，1 H '，2,2'-双吲哚和N-芳基吡咯与NH 4的异丁酮介导的硫氰酸氰化反应方便地获得SCN。还研究了转换的范围和局限性。
• Transition-metal-free regioselective thiocyanation of phenols, anilines and heterocycles
  作者：Trimbak B. Mete、Tushar M. Khopade、Ramakrishna G. Bhat

  DOI：10.1016/j.tetlet.2016.12.043

  日期：2017.2

  An expedient direct and regioselective thiocyanation of phenols, anilines and heterocycles is described. Transformation is realized via the direct CH functionalization under transition metal free conditions at ambient temperature in excellent yields. Method proved to be monoselective and variety of functional groups tolerated the reaction conditions. The practicality of the protocol is demonstrated

  描述了酚，苯胺和杂环的方便的直接和区域选择性的硫氰化。通过在无过渡金属条件下于环境温度下直接C H官能化以优异的收率实现转化。方法被证明是单选择性的，并且各种官能团都能耐受反应条件。该协议的实用性在PPARδ激动剂前体的克级合成中得到了很好的证明。
• <i>N</i>-Thiocyanato-dibenzenesulfonimide: a new electrophilic thiocyanating reagent with enhanced reactivity
  作者：Chengqiu Li、Pingliang Long、Haopeng Wu、Hongquan Yin、Fu-Xue Chen

  DOI：10.1039/c9ob01340g

  日期：——

  A novel electrophilic thiocyanating reagent, N-thiocyanato-dibenzenesulfonimide, was prepared and exhibited enhanced electrophilicity with a wide scope of substrates. Thus, it reacted with activated aromatics such as phenols, indoles, anilines and anisoles without a catalyst giving the corresponding thicyanate derivatives in high yields, while TfOH for unactivated arenes and hetero aromatics and Zn(OTf)2

  制备了一种新型的亲电子硫氰酸化试剂，N-硫氰基-二苯磺酰亚胺，并在广泛的底物范围内表现出增强的亲电子性。因此，它与活化的芳族化合物（如苯酚，吲哚，苯胺和茴香醚）在没有催化剂的情况下以高收率反应生成相应的硫氰酸盐衍生物，而未活化的芳烃和杂芳族化合物的TfOH和酮的Zn（OTf）2被用作催化剂，分别。值得注意的是，内部烯烃和苯乙烯被双官能化，从而以高收率得到1,2-氨基硫氰酸酯。
• Indium-mediated Allylation of Heteroaryl, Benzyl, and Cinnamyl Thiocyanates: A Novel Route for 3-(Allylsulfanyl)-1<i>H</i>-indoles
  作者：J. S. Yadav、B. V. Subba Reddy、D. Chandrakanth、A. V. Hara Gopal

  DOI：10.1246/cl.2008.1082

  日期：2008.10.5

  Heteroaryl, benzyl, and cinnamyl thiocyanates undergo smooth allylation with allyl bromide in the presence of indium or zinc metal in THF at room temperature to produce the corresponding allyl sulfides in good yields and with high selectivity.

  杂芳基、苄基和肉桂基硫氰酸酯在铟或锌金属的存在下在 THF 中在室温下与烯丙基溴进行平滑的烯丙基化，以良好的收率和高选择性制备相应的烯丙基硫化物。
• 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane Bis(tetrafluoroborate) as Novel and Versatile Reagent for the Rapid Thiocyanation of Indoles, Azaindole, and Carbazole
  作者：J. S. Yadav、B. V. Subba Reddy、Y. Jayasudhan Reddy

  DOI：10.1246/cl.2008.652

  日期：2008.6.5

  SelectfluorTM is found to catalyze efficiently the electrophilic thiocyanation of indoles and pyrrole with ammonium thiocyanate under mild and neutral conditions to produce the corresponding 3-indolyl and 2-pyrrolyl thiocyanates, respectively, in excellent yields with high selectivity. This method is effective even with azaindole and carbazole while many of reported procedures failed to produce thiocyanates

  SelectfluorTM 被发现在温和和中性条件下有效地催化吲哚和吡咯与硫氰酸铵的亲电硫氰化反应，分别以高产率和高选择性制备相应的 3-吲哚基和 2-吡咯基硫氰酸酯。该方法甚至对氮杂吲哚和咔唑也有效，而许多报道的程序未能从氮杂吲哚产生硫氰酸盐。