3-(4-chlorophenylselanyl)-1-methyl-1H-indole | 1415019-26-9

• 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-(4-chlorophenylselanyl)-1-methyl-1H-indole
• 英文别名: CMI；3-((4-Chlorophenyl)selanyl)-1-methyl-1h-indole；3-(4-chlorophenyl)selanyl-1-methylindole
• CAS: 1415019-26-9
• 化学式: C₁₅H₁₂ClNSe
• 分子量: 320.68
• InChiKey: QDNQVTLDUDGOCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-甲基吲哚 、 双(4-氯苯基)二硒化物 在 copper(l) iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以82%的产率得到3-(4-chlorophenylselanyl)-1-methyl-1H-indole
  参考文献：
  名称：

  Sonochemistry: An efficient alternative to the synthesis of 3-selanylindoles using CuI as catalyst

  摘要：

  Ultrasonic (US) irradiation was successfully used as an alternative energy source to prepare 3-selanylindoles through the direct selanylation of indoles with diorganyl diselenides using CuI (20 mol%) as catalyst and DMSO as the solvent. By using this US-promoted reaction, eleven 3-organylselanylindoles were prepared selectively and in good yields. A comparative study between the reactions under conventional heating, microwave and ultrasound irradiations was performed, and it was observed advantage in using US over the other heating systems. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2015.05.012

文献信息

• A Selenium-Based Ionic Liquid as a Recyclable Solvent for the Catalyst-Free Synthesis of 3-Selenylindoles
  作者：Everton Zimmermann、Samuel Thurow、Camilo Freitas、Samuel Mendes、Gelson Perin、Diego Alves、Raquel Jacob、Eder Lenardão

  DOI：10.3390/molecules18044081

  日期：——

  The ionic liquid 1-butyl-3-methylimidazolium methylselenite, [bmim][SeO2(OCH3)], was successfully used as solvent in the catalyst-free preparation of 3-arylselenylindoles by the reaction of indole with ArSeCl at room temperature. The products were obtained selectively in good yields without the need of any additive and the solvent was easily reused for several cycles with good results.

  离子液体1-丁基-3-甲基咪唑鎓甲基亚硒酸盐[bmim][SeO2(OCH3)]成功地用作溶剂，在室温下通过吲哚与ArSeCl反应无催化剂制备3-芳基硒基吲哚。无需任何添加剂即可以良好的收率选择性地获得产物，并且溶剂可以轻松重复使用多个循环，效果良好。
• Micelle-mediated multicomponent cross-coupling in water: general construction of 3-chalcogenylindoles
  作者：Xi He、Weili Song、Xuemin Liu、Jiamin Huang、Ruilong Feng、Shaodong Zhou、Jianquan Hong、Xin Ge

  DOI：10.1039/d2gc03694k

  日期：——

  A general and sustainable multicomponent cross-coupling for the construction of 3-chalcogenylindoles from indoles with aryl iodides and elemental sulfur under the aqueous micellar condition was developed. Elemental sulfur is employed as an eco-friendly and easy-handling sulfur source of thiyl radicals. The synergic effect between Cu catalysts and micelles formed by the sugar-based surfactant GluM can

  开发了一种通用且可持续的多组分交叉偶联，用于在水性胶束条件下从吲哚与芳基碘化物和元素硫构建 3-硫属吲哚。元素硫被用作一种环保且易于处理的硫自由基硫源。Cu 催化剂和糖基表面活性剂 GluM 形成的胶束之间的协同作用可以稳定硫自由基，进一步通过单电子转移在容易获得的吲哚上引发 C-S 偶联。值得注意的是，水性胶束系统不仅可以回收再利用，收率高，而且还可以扩展到元素硒的转化。
• Efficient synthesis of 3-selanyl- and 3-sulfanylindoles employing trichloroisocyanuric acid and dichalcogenides
  作者：Claudio C. Silveira、Samuel R. Mendes、Lucas Wolf、Guilherme M. Martins、Lisandro von Mühlen

  DOI：10.1016/j.tet.2012.09.022

  日期：2012.12

  3-Arylselanyl- and 3-arylsulfanylindoles were prepared in EtOAc, by the reaction of indole with the diaryl dichalcogenide-trichloroisocyanuric acid (TCCA) reagent system. The products were efficiently and conveniently obtained, at room temperature and in short reaction times. (C) 2012 Elsevier Ltd. All rights reserved.
• Direct selenation of imidazoheterocycles and indoles with selenium powder in a copper-catalyzed three-component one-pot system
  作者：Tao Guo、Zhe Dong、Panke Zhang、Weiqin Xing、Liping Li

  DOI：10.1016/j.tetlet.2018.05.046

  日期：2018.6

  An efficient and convenient Cu-catalyzed three-component reaction is described for the selenation of imidazoheterocycles/indoles with Se powder and aryl iodides. This procedure provides diverse 3-arylselenylimidazoheterocycles and 3-arylselenylindoles with good yields and functional group tolerance. Some of the products exhibited better or comparable antiproliferative activities compared with the positive control 5-fluorouracil against H1975, PC-9, HGC-27, EC-109, and MCF-7 cancer cell lines. (C) 2018 Elsevier Ltd. All rights reserved.
• Sonochemistry: An efficient alternative to the synthesis of 3-selanylindoles using CuI as catalyst
  作者：Beatriz M. Vieira、Samuel Thurow、Juliana S. Brito、Gelson Perin、Diego Alves、Raquel G. Jacob、Claudio Santi、Eder J. Lenardão

  DOI：10.1016/j.ultsonch.2015.05.012

  日期：2015.11

  Ultrasonic (US) irradiation was successfully used as an alternative energy source to prepare 3-selanylindoles through the direct selanylation of indoles with diorganyl diselenides using CuI (20 mol%) as catalyst and DMSO as the solvent. By using this US-promoted reaction, eleven 3-organylselanylindoles were prepared selectively and in good yields. A comparative study between the reactions under conventional heating, microwave and ultrasound irradiations was performed, and it was observed advantage in using US over the other heating systems. (C) 2015 Elsevier B.V. All rights reserved.