ethyl 2-(((trifluoromethyl)sulfonyl)oxy)-1H-indole-1-carboxylate | 880263-69-4

• 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 2-(((trifluoromethyl)sulfonyl)oxy)-1H-indole-1-carboxylate
• 英文别名: Ethyl 2-(trifluoromethylsulfonyloxy)indole-1-carboxylate
• CAS: 880263-69-4
• 化学式: C₁₂H₁₀F₃NO₅S
• 分子量: 337.276
• InChiKey: SRISHOIOPCBVEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2-(((trifluoromethyl)sulfonyl)oxy)-1H-indole-1-carboxylate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以76%的产率得到ethyl 2-hydroxy-3-(trifluoromethylsulfonyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  JP5943387

  摘要：

  公开号：
• 作为产物：
  描述：

  Ethyl 2-ethoxycarbonyloxyindole-1-carboxylate 在 ammonium carbonate 、 2,4,6-三叔丁基吡啶 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 ethyl 2-(((trifluoromethyl)sulfonyl)oxy)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Regioselective Synthesis of Heteroaryl Triflones by LDA (Lithium Diisopropylamide)-Mediated Anionic Thia-Fries Rearrangement

  摘要：

  Novel heteroaryl triflones including oxindole, pyrazolone, pyridine, and quinoline derivatives have been regioselectively synthesized by LDA-mediated thia-Fries rearrangement for the first time. These reactions are also the first examples of the application of anionic thia-Fries rearrangement in heteroaromatic compounds.

  DOI：

  10.1021/ol300842d

文献信息

• 2-Trifluoromethanesulfonyloxyindole-1-carboxylic Acid Ethyl Ester: A Practical Intermediate for the Synthesis of 2-Carbosubstituted Indoles
  作者：Elisabetta Rossi、Giorgio Abbiati、Valentina Canevari、Giuseppe Celentano、Elsa Magri

  DOI：10.1055/s-2005-918509

  日期：——

  Ready accessible 2-trifluoromethanesulfonyloxyindole-1-carboxylic acid ethyl ester undergoes palladium-catalyzed coupling reactions with different partners giving rise to 2-aryl, heteroaryl, vinyl, allyl, and alkynyl indoles in good to excellent yields.

  可获得的2-三氟甲磺酰氧印吲哚-1-羧酸乙酯与不同的反应伙伴在钯催化下发生偶联反应，生成良好到优异收率的2-芳基、杂芳基、乙烯基、烯丙基和炔基印吲哚。
• Exploiting the σ-phylic properties of cationic gold(<scp>i</scp>) catalysts in the ring opening reactions of aziridines with indoles
  作者：Elisabetta Rossi、Giorgio Abbiati、Monica Dell'Acqua、Marco Negrato、Andrea Paganoni、Valentina Pirovano

  DOI：10.1039/c6ob00672h

  日期：——

  A study on the SN2-type ring opening reactions of aziridines with indoles as nucleophiles is reported. Under gold(I) catalysis a great variety of tryptamine derivatives were prepared in good to excellent yields with complete stereocontrol when chiral aziridines were used. We demonstrated that cationic gold(I) catalysts are superior Lewis acids to the previously reported group 3, 12 and 13 metals in

  在S A研究Ñ报道氮丙啶与吲哚作为亲核试剂2型开环反应。在金（I）催化下，当使用手性氮丙啶类化合物时，以良好的产率和优异的产率制备了多种色胺，具有完全的立体控制。我们证明，就催化剂载量和反应产率而言，阳离子金（I）催化剂是优于先前报道的第3、12和13组金属的路易斯酸。此外，观察到了2-苯基-N-甲苯磺酰氮丙啶的完全区域选择性。而使用2-甲基-N时，区域选择性高达10：1-甲苯磺酰氮丙啶。最后，还报道了对引起吡咯并吲哚啉的脱芳香化反应的初步研究。
• [Copper(I)(Pyridine-Containing Ligand)] Catalyzed Regio- and Steroselective Synthesis of 2-Vinylcyclopropa[<i>b</i>]indolines from 2-Vinylindoles
  作者：Valentina Pirovano、Elisa Brambilla、Giorgio Tseberlidis

  DOI：10.1021/acs.orglett.7b03704

  日期：2018.1.19

  A [copper(I)pyridine-containing ligand]-catalyzed reaction between 2-vinylindoles and diazo esters is described. The reaction allows for the synthesis of a series of 2-vinylcyclopropa[b]indolines with excellent levels of regio- and sterocontrol under mild conditions.

  描述了2-乙烯基吲哚和重氮酯之间的[含铜（I）吡啶的配体]催化的反应。该反应允许在温和条件下合成一系列具有优异的区域控制和立体控制水平的2-乙烯基环丙基[ b ]二氢吲哚。
• Gold-catalyzed synthesis of tetrahydrocarbazole derivatives through an intermolecular cycloaddition of vinyl indoles and N-allenamides
  作者：Valentina Pirovano、Laura Decataldo、Elisabetta Rossi、Rubén Vicente

  DOI：10.1039/c3cc41514g

  日期：——

  A gold-catalyzed formal [4+2] cycloaddition of vinyl indoles and N-allenamides leading to tetrahydrocarbazoles is described. Moreover, new multicomponent reactions of vinyl indoles with two allene molecules are reported.

  描述了金催化的乙烯基吲哚和N-烯丙基酰胺的正式[4 + 2]环加成反应，生成四氢咔唑。此外，已经报道了乙烯基吲哚与两个烯丙基分子的新的多组分反应。
• Novel Domino Approach to Fluorescent Pyrimido[1,6-a]indolones
  作者：Elisabetta Rossi、Diego Facoetti、Giorgio Abbiati、Laura d’Avolio、Lutz Ackermann

  DOI：10.1055/s-0029-1217807

  日期：2009.9

  Easily accessible N-ethoxycarbonyl-2-alkynylindoles undergo, in the presence of primary aryl amines and under TiCl4/t-BuNH2 catalysis, domino hydroamination-annulation reactions giving rise to pyrimido[1,6-a]indolones in good to excellent yields. The reaction involves an initial highly regio- and chemoselective hydroamination reaction. The obtained compounds show interesting fluorescence properties and could represent a new class of useful markers for bioanalytical purpose.

  易于获取的N-乙氧基碳酰基-2-烷基炔基吲哚在初级芳基胺存在下，经过TiCl4/t-BuNH2催化，发生多步水氨化-环化反应，得到吡啶[1,6-a]吲哚酮，产率良好到优秀。该反应涉及初始的高度区域和化学选择性的水氨化反应。获得的化合物显示出有趣的荧光特性，可以代表一类新的有用的生物分析标记物。