5-bromo-3-(4-chlorophenylselanyl)-1H-indole | 1415019-24-7

• 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-bromo-3-(4-chlorophenylselanyl)-1H-indole
• 英文别名: 5-bromo-3-((4-chlorophenyl)selenyl)-1H-indole；5-bromo-3-(4-chlorophenyl)selanyl-1H-indole
• CAS: 1415019-24-7
• 化学式: C₁₄H₉BrClNSe
• 分子量: 385.549
• InChiKey: JWRIPPNKLZMXBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  5-溴吲哚 、 双(4-氯苯基)二硒化物 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以87%的产率得到5-bromo-3-(4-chlorophenylselanyl)-1H-indole
  参考文献：
  名称：

  环保条件下3-硒代吲哚的合成

  摘要：

  探索了通过使用催化量的 K2CO3 和乙醇作为开放空气系统中的生物溶剂，通过更环保的方案制备生物相关的 3-硒代吲哚。通过这种简单的方法，通过自由基途径以良好的收率获得了具有不同功能的 3-硒代吲哚。

  DOI：

  10.1002/ejoc.201500514

文献信息

• Synthesis of 3-Selenylindoles under Eco­friendly Conditions
  作者：Natasha L. Ferreira、Juliano B. Azeredo、Breno L. Fiorentin、Antonio L. Braga

  DOI：10.1002/ejoc.201500514

  日期：2015.8

  The preparation of biologically relevant 3-selenylindoles by a greener protocol by using a catalytic amount of K2CO3 and ethanol as a biosolvent in a system open to air was explored. Through this easy approach, 3-selenylindoles with different functionalities were obtained in good yields by a radical pathway.

  探索了通过使用催化量的 K2CO3 和乙醇作为开放空气系统中的生物溶剂，通过更环保的方案制备生物相关的 3-硒代吲哚。通过这种简单的方法，通过自由基途径以良好的收率获得了具有不同功能的 3-硒代吲哚。
• 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。
• 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.
• 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.
• NH4I-catalyzed chalcogen(S/Se)-functionalization of 5-membered N-heteroaryls under metal-free conditions
  作者：Luana Bettanin、Sumbal Saba、Carlos V. Doerner、Marcelo S. Franco、Marcelo Godoi、Jamal Rafique、Antonio L. Braga

  DOI：10.1016/j.tet.2018.05.084

  日期：2018.7

  Herein, we described the NH4I-catalyzed C-H bond chalcogenation of N-heteroaryls in the presence of a minimum amount of DMSO/H2O/acetic acid as additives (2.5/2.5/1 M equiv., respectively), under metal-free conditions. Under optimized conditions, a wide variety of sulfenyl/selenyl imidazo[1,2-alpha]pyridines were prepared in very good yields. Moreover, the present approach was also highly efficient for the chalcogenation of different 5-membered N-heteroaryls, e.g., indole, imidazothiazole, indazole and imidazopyrimidine derivatives. (C) 2018 Elsevier Ltd. All rights reserved.