ethyl 5-bromo-1-(3-chlorophenyl)-1H-indole-2-carboxylate | 1186429-51-5

• 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: ethyl 5-bromo-1-(3-chlorophenyl)-1H-indole-2-carboxylate
• 英文别名: Ethyl 5-bromo-1-(3-chlorophenyl)indole-2-carboxylate；ethyl 5-bromo-1-(3-chlorophenyl)indole-2-carboxylate
• CAS: 1186429-51-5
• 化学式: C₁₇H₁₃BrClNO₂
• 分子量: 378.653
• InChiKey: VSWCMXVRKAJIKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 5-bromo-1-(3-chlorophenyl)-1H-indole-2-carboxylate 在 sodium azide 、 copper(l) chloride 作用下， 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 3.6h， 生成
  参考文献：
  名称：

  Indirect C–H Azidation of Heterocycles via Copper-Catalyzed Regioselective Fragmentation of Unsymmetrical λ³-Iodanes

  摘要：

  A C-H bond of electron-rich heterocycles is transformed into a C-N bond in a reaction sequence comprising the formation of heteroaryl(phenyl)iodonium azides and their in situ regioselective fragmentation to heteroaryl azides. A Cu(I) catalyst ensures complete regiocontrol in the fragmentation step and catalyzes the subsequent 1,3-dipolar cycloaddition of the formed azido heterocycles with acetylenes. The heteroaryl azides can also be conveniently reduced to heteroarylamines by aqueous ammonium sulfide. The overall C-H to C-N transformation is a mild and operationally simple one-pot sequential multistep process.

  DOI：

  10.1021/ja305574k
• 作为产物：
  描述：

  5-溴吲哚-2-羧酸乙酯 、 3-氯苯硼酸 在 吡啶 、 copper diacetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以89%的产率得到ethyl 5-bromo-1-(3-chlorophenyl)-1H-indole-2-carboxylate
  参考文献：
  名称：

  Catalytic Direct Acetoxylation of Indoles

  摘要：

  3-Acetoxylndole-2-carboxylates could be readily synthesized in a Pd(OAC)(2)- or PtCl2-catalyzed direct C-3 acetoxylation of indole-2-carboxylates using PhI(OAC)(2) as a terminal oxidant.

  DOI：

  10.1021/jo901321b

文献信息

• Copper-Catalyzed Intermolecular C–H Amination of (Hetero)arenes via Transient Unsymmetrical λ³-Iodanes
  作者：Igors Sokolovs、Dmitrijs Lubriks、Edgars Suna

  DOI：10.1021/ja502174d

  日期：2014.5.14

  A one-pot two-step method for intermolecular C-H amination of electron-rich heteroarenes and arenes has been developed. The approach is based on a room-temperature copper-catalyzed regioselective reaction of the in situ formed unsymmetrical (hetero)aryl-λ(3)-iodanes with a wide range of primary and secondary aliphatic amines and anilines.

  已经开发了一种用于富电子杂芳烃和芳烃的分子间 CH 胺化的一锅两步法。该方法基于室温铜催化的区域选择性反应，即原位形成的不对称（杂）芳基-λ(3)-碘烷与多种脂肪族伯胺和仲胺和苯胺。
• Indirect C–H Azidation of Heterocycles via Copper-Catalyzed Regioselective Fragmentation of Unsymmetrical λ³-Iodanes
  作者：Dmitrijs Lubriks、Igors Sokolovs、Edgars Suna

  DOI：10.1021/ja305574k

  日期：2012.9.19

  A C-H bond of electron-rich heterocycles is transformed into a C-N bond in a reaction sequence comprising the formation of heteroaryl(phenyl)iodonium azides and their in situ regioselective fragmentation to heteroaryl azides. A Cu(I) catalyst ensures complete regiocontrol in the fragmentation step and catalyzes the subsequent 1,3-dipolar cycloaddition of the formed azido heterocycles with acetylenes. The heteroaryl azides can also be conveniently reduced to heteroarylamines by aqueous ammonium sulfide. The overall C-H to C-N transformation is a mild and operationally simple one-pot sequential multistep process.
• Catalytic Direct Acetoxylation of Indoles
  作者：Ilga Mutule、Edgars Suna、Kristofer Olofsson、Benjamin Pelcman

  DOI：10.1021/jo901321b

  日期：2009.9.18

  3-Acetoxylndole-2-carboxylates could be readily synthesized in a Pd(OAC)(2)- or PtCl2-catalyzed direct C-3 acetoxylation of indole-2-carboxylates using PhI(OAC)(2) as a terminal oxidant.