1-Methyl-2-(trifluoromethyl)-5-bromo-1H-indole | 1367875-90-8

• 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: 1-Methyl-2-(trifluoromethyl)-5-bromo-1H-indole
• 英文别名: 5-bromo-1-methyl-2-(trifluoromethyl)indole
• CAS: 1367875-90-8
• 化学式: C₁₀H₇BrF₃N
• 分子量: 278.071
• InChiKey: SMLINMDBDOKGEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-2(1H)-quinoxalinone 、 1-Methyl-2-(trifluoromethyl)-5-bromo-1H-indole 、 Langlois reagent 在 copper (II)-fluoride 、 dipotassium peroxodisulfate 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以43%的产率得到3-[5-bromo-1-methyl-2-(trifluoromethyl)-1H-indol-3-yl]-1-methylquinoxalin-2(1H)-one
  参考文献：
  名称：

  Copper‐Catalyzed Multicomponent Reaction to Construct Fluorinated Indole‐quinoxalin‐2(1 H )‐ones and Their Biological Evaluation

  摘要：

  AbstractA practical and mild three‐component reaction of indoles, quinoxalin‐2(1H)‐ones, and CF3SO2Na is disclosed for the facile access of various 3‐[2‐(trifluoromethyl)1H‐indol‐3‐yl]quinoxalin‐2(1H)‐ones using low‐cost and catalytic amount of CuF2 as the catalyst. This strategy exhibits high site‐selectivity, step economy, and broad substrates scope. Synthetic utility was demonstrated by the one‐pot two‐step synthesis of N‐alkyl triazoles compounds via a click chemistry. To evaluate the antiproliferative activity of these compounds, A549 s (human lung adenocarcinoma cells) and HUVECs, as a model of toxicity, were used in MTT assay. The outcomes disclosed for 6‐CO2Me and a N‐alkyl triazole derivatives were of potent antiproliferative effect against A549 s (IC50 = 4.7 and 14.9 μM, respectively) with slight cytotoxicity in HUVECs. Morphological study was conducted by AO/EB dual staining, indicated hydrochloride 6‐CO2Me derivative was capable of inducing apoptosis of A549 cells.

  DOI：

  10.1002/ejoc.202200696
• 作为产物：
  描述：

  5-溴-1-甲基吲哚 、 三氟碘甲烷 在 tris(bipyridine)ruthenium(II) dichloride hexahydrate 、 四甲基乙二胺 作用下， 以 乙腈 为溶剂， 生成 5-bromo-1-methyl-3-(trifluoromethyl)-1H-indole 、 1-Methyl-2-(trifluoromethyl)-5-bromo-1H-indole
  参考文献：
  名称：

  Trifluoromethylation of heterocycles via visible light photoredox catalysis

  摘要：

  A method has been developed for the visible light-induced trifluoromethylation of heterocyclic compounds. A variety of electron-rich heterocycles were transformed into trifluoromethylated products by using CF3I as the trifluoromethyl radical source and Ru(bpy)(3)Cl-2 as the photocatalyst under mild reaction conditions. This operationally simple and eco-friendly process can introduce trifluoromethyl groups without prefunctionalization. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.032

文献信息

• Trifluoromethylation of heterocycles via visible light photoredox catalysis
  作者：Naeem Iqbal、Sungkyu Choi、Euna Ko、Eun Jin Cho

  DOI：10.1016/j.tetlet.2012.02.032

  日期：2012.4

  A method has been developed for the visible light-induced trifluoromethylation of heterocyclic compounds. A variety of electron-rich heterocycles were transformed into trifluoromethylated products by using CF3I as the trifluoromethyl radical source and Ru(bpy)(3)Cl-2 as the photocatalyst under mild reaction conditions. This operationally simple and eco-friendly process can introduce trifluoromethyl groups without prefunctionalization. (C) 2012 Elsevier Ltd. All rights reserved.
• Copper‐Catalyzed Multicomponent Reaction to Construct Fluorinated Indole‐quinoxalin‐2(1 <i>H</i> )‐ones and Their Biological Evaluation
  作者：Letian Zhang、Yong Yang、Pengfei Zhang、Chao Chen、Chao Shen

  DOI：10.1002/ejoc.202200696

  日期：2022.9.20

  AbstractA practical and mild three‐component reaction of indoles, quinoxalin‐2(1H)‐ones, and CF3SO2Na is disclosed for the facile access of various 3‐[2‐(trifluoromethyl)1H‐indol‐3‐yl]quinoxalin‐2(1H)‐ones using low‐cost and catalytic amount of CuF2 as the catalyst. This strategy exhibits high site‐selectivity, step economy, and broad substrates scope. Synthetic utility was demonstrated by the one‐pot two‐step synthesis of N‐alkyl triazoles compounds via a click chemistry. To evaluate the antiproliferative activity of these compounds, A549 s (human lung adenocarcinoma cells) and HUVECs, as a model of toxicity, were used in MTT assay. The outcomes disclosed for 6‐CO2Me and a N‐alkyl triazole derivatives were of potent antiproliferative effect against A549 s (IC50 = 4.7 and 14.9 μM, respectively) with slight cytotoxicity in HUVECs. Morphological study was conducted by AO/EB dual staining, indicated hydrochloride 6‐CO2Me derivative was capable of inducing apoptosis of A549 cells.