N-[4-chloro-2-(2,2-dibromoethenyl)phenyl]methanesulfonamide | 1259577-28-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[4-chloro-2-(2,2-dibromoethenyl)phenyl]methanesulfonamide
• CAS: 1259577-28-0
• 化学式: C₉H₈Br₂ClNO₂S
• 分子量: 389.495
• InChiKey: XQTDQMJJIPSWEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[4-chloro-2-(2,2-dibromoethenyl)phenyl]methanesulfonamide 在 caesium carbonate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以94%的产率得到2-Bromo-5-chloro-1-methylsulfonylindole
  参考文献：
  名称：

  The facile synthesis of 2-bromoindoles via Cs₂CO₃-promoted intramolecular cyclization of 2-(gem-dibromovinyl)anilines under transition-metal-free conditions

  摘要：

  在不含过渡金属的条件下，通过 Cs2CO3 促进的 2-(偕溴乙烯基)-N-甲基磺酰基苯胺的分子内环化，可以轻松制备 2-溴吲哚，收率优异。该方法可以扩展到相应的 2-氯吲哚的合成。反应机理表明，环化是通过关键中间体苯乙炔基溴发生的，然后是一锅环化。

  DOI：

  10.1039/c2ra22172a
• 作为产物：
  描述：

  4-氯-2-(2,2-二溴乙烯基)苯胺 、 甲基磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 N-[4-chloro-2-(2,2-dibromoethenyl)phenyl]methanesulfonamide
  参考文献：
  名称：

  Facile synthesis of 2-bromoindoles by ligand-free CuI-catalyzed intramolecular cross-coupling of gem-dibromoolefins

  摘要：

  A mild and efficient synthesis of 2-bromoindoles by ligand-free CuI-catalyzed intramolecular cross-coupling of gem-dibromoolefins was developed. Reactions were carried out in toluene at room temperature and the corresponding 2-bromoindoles were obtained in excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.129

文献信息

• Microwave irradiated synthesis of 2-bromo(chloro)indoles via intramolecular cyclization of 2-(gem-dibromo(chloro)vinyl)anilines in the presence of TBAF under metal-free conditions
  作者：Min Wang、Pinhua Li、Wei Chen、Lei Wang

  DOI：10.1039/c4ra00603h

  日期：——

  2-Bromo(chloro)indoles were readily prepared through TBAF-promoted intramolecular cyclization of 2-(gem-dibromo(chloro)vinyl)anilines in excellent yields under metal-free and microwave irradiation conditions.

  2-溴（氯）吲哚可通过TBAF促进的2-（gem-二溴（氯）乙烯）苯胺的分子内环化反应，在无金属和微波辐射条件下，以极高的产率轻松制备。
• An efficient synthesis of 2-bromo(chloro)-3-selenyl(sulfenyl)indoles via tandem reactions of 2-(gem-dibromo(chloro)vinyl)anilines with diselenides(disulfides)
  作者：Jie Liu、Pinhua Li、Wei Chen、Lei Wang

  DOI：10.1039/c2cc34800d

  日期：——

  A novel and efficient synthesis of 2-bromo(chloro)-3-selenyl(sulfenyl)indoles through tandem reactions of 2-(gem-dibromo(chloro)vinyl)-N-methylsulfonylanilines with diselenides and disulfides in the presence of t-BuOLi and I2 (10 mol%) in DMSO was developed. The reactions generated the desired products in good yields with high regio-selectivity under transition-metal-free conditions in one-pot.

  在 t-BuOLi 存在下，通过 2-(gem-二溴(氯)乙烯基)-N-甲基磺酰苯胺与二硒化物和二硫化物的串联反应，新型高效合成 2-溴(氯)-3-硒基(硫基)吲哚开发了 I2 (10 mol%) 的 DMSO 溶液。该反应在不含过渡金属的条件下一锅法以良好的收率和高区域选择性生成了所需的产物。
• Facile synthesis of 2-bromoindoles by ligand-free CuI-catalyzed intramolecular cross-coupling of gem-dibromoolefins
  作者：Baishan Jiang、Kemei Tao、Wang Shen、Jiancun Zhang

  DOI：10.1016/j.tetlet.2010.09.129

  日期：2010.12

  A mild and efficient synthesis of 2-bromoindoles by ligand-free CuI-catalyzed intramolecular cross-coupling of gem-dibromoolefins was developed. Reactions were carried out in toluene at room temperature and the corresponding 2-bromoindoles were obtained in excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.
• The facile synthesis of 2-bromoindoles via Cs₂CO₃-promoted intramolecular cyclization of 2-(gem-dibromovinyl)anilines under transition-metal-free conditions
  作者：Pinhua Li、Yong Ji、Wei Chen、Xiuli Zhang、Lei Wang

  DOI：10.1039/c2ra22172a

  日期：——

  2-Bromoindoles were readily prepared through a facile Cs2CO3-promoted intramolecular cyclization of 2-(gem-bromovinyl)-N-methylsulfonylanilines in excellent yields under transition-metal-free conditions. This methodology could be extended to the synthesis of corresponding 2-chloroindoles. The reaction mechanism suggested that cyclization occurs through a key intermediate, phenylethynyl bromide, followed by cyclization in one-pot.

  在不含过渡金属的条件下，通过 Cs2CO3 促进的 2-(偕溴乙烯基)-N-甲基磺酰基苯胺的分子内环化，可以轻松制备 2-溴吲哚，收率优异。该方法可以扩展到相应的 2-氯吲哚的合成。反应机理表明，环化是通过关键中间体苯乙炔基溴发生的，然后是一锅环化。