ethyl 3-(trifluoromethyl)-1H-indole-2-carboxylate

• 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 3-(trifluoromethyl)-1H-indole-2-carboxylate
• 英文别名: 3-(Trifluoromethyl)-1H-indole-2-carboxylic acid ethyl ester
• 化学式: C₁₂H₁₀F₃NO₂
• 分子量: 257.212
• InChiKey: YDEFLIABYVHEDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 、 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， 以81%的产率得到ethyl 3-(trifluoromethyl)-1H-indole-2-carboxylate
  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

• Rational Design and Development of<scp>Low‐Price</scp>, Scalable,<scp>Shelf‐Stable</scp>and Broadly Applicable Electrophilic Sulfonium<scp>Ylide‐Based</scp>Trifluoromethylating Reagents
  作者：Yafei Liu、Yijing Ling、Hangming Ge、Long Lu、Qilong Shen

  DOI：10.1002/cjoc.202100107

  日期：2021.6

  reagents (trifluoromethyl)(4-nitrophenyl)bis(carbomethoxy)methylide (1g) and (trifluoromethyl)(3-chlorophenyl)bis(carbomethoxy)methylide (1j) through structure-activity study was described. Under mild conditions, reagent 1g reacted with β-ketoesters and silyl enol ethers to give α-trifluoromethylated-β-ketoesters or α-trifluoromethylated ketones in high yields. In addition, reagent 1g could serve as

  通过结构活性研究，描述了两种高反应性亲电三氟甲基化试剂（三氟甲基）（4-硝基苯基）双（羰基甲氧基）亚甲基（1g）和（三氟甲基）（3-氯苯基）双（羰基甲氧基）亚甲基（1j）的开发。在温和的条件下，试剂1g与β-酮酸酯和甲硅烷基烯醇醚反应，以高收率得到α-三氟甲基化的β-酮酸酯或α-三氟甲基化的酮。另外，试剂1g可以在可见光照射下用作多种三氟甲基化转变的三氟甲基自由基，包括富电子吲哚和吡咯和芳基亚磺酸钠的自由基三氟甲基化，以及苯乙烯衍生物的三氟甲基化双官能化。另一方面，作为补充，在还原偶联条件下，试剂1j与多种（杂）芳基碘化物反应以形成三氟甲基化的（杂）芳烃。
• Synthèse de perfluoroalkyl indoles via la cycloaddition dipolaire-1,3
  作者：Joel Fayn、Antoine Nezis、Aime Cambon

  DOI：10.1016/s0022-1139(00)81989-2

  日期：1987.9

  An unusual synthesis of functionalized F-alkyl indoles using ethyl perfluoroalkynoates and C,N diphenyl nitrone is described. Two isomers, 2- F-alkyl (90%) and 3- F-alkyl (10%) are obtained with short perfluoro alkyl chains (CF3, nC3F7). Regiospecifity is obtained with longer chains (C5F11, C6F13, C7F15).

  描述了使用全氟链烷酸乙酯和C，N二苯基硝酮不寻常地合成官能化的F-烷基吲哚的方法。获得具有短的全氟烷基链（CF 3，nC 3 F 7）的两种异构体，2-F-烷基（90％）和3-F-烷基（10％）。区域特异性是通过更长的链（C 5 F 11，C 6 F 13，C 7 F 15）获得的。
• Radical CH Functionalization of Heteroarenes under Electrochemical Control
  作者：Alexander G. O'Brien、Akinobu Maruyama、Yasuhide Inokuma、Makoto Fujita、Phil S. Baran、Donna G. Blackmond

  DOI：10.1002/anie.201407948

  日期：2014.10.27

  Electrochemical reactions are shown to be effective for the CH functionalization of a number of heterocyclic substrates that are recalcitrant to conventional peroxide radical initiation conditions. Monitoring reaction progress under electrochemical conditions provides mechanistic insight into the CH functionalization of a series of heterocycles of interest in medicinal chemistry.

  电化学反应被证明对于许多杂环底物的C = H 官能化是有效的，这些底物对传统的过氧化物自由基引发条件是不利的。监测电化学条件下的反应进程为药物化学中一系列感兴趣的杂环化合物的C → H 官能化提供了机制见解。
• Metal-Free Photocatalytic Radical Trifluoromethylation Utilizing Methylene Blue and Visible Light Irradiation
  作者：Spencer P. Pitre、Christopher D. McTiernan、Hossein Ismaili、Juan C. Scaiano

  DOI：10.1021/cs5005823

  日期：2014.8.1

  The use of organofluorine compounds, especially those with an incorporated trifluoromethyl moiety, has increased dramatically in both the pharmaceutical and agrochemical industry. It has therefore become imperative to develop a mild and efficient synthetic technique for the inclusion of trifluoromethyl groups. Herein, we report the first use of methylene blue as a photosensitizer for the catalytic radical trifluoro- and hydrotrifluoromethylation of electron-rich heterocycles as well as terminal alkenes and alkynes under visible light irradiation. These reactions proceed with moderate to good yields at low catalyst concentrations; short irradiation times; and most importantly, without the need for potentially toxic transition-metal catalysts. In this work, considerable emphasis was also placed on understanding the kinetics of the mechanistically key steps through the use of laser flash photolysis techniques to more efficiently optimize the reaction conditions.
• 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.