ethyl 2-(phenylethynyl)-1H-indole-1-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 2-(phenylethynyl)-1H-indole-1-carboxylate
• 英文别名: Ethyl 2-(2-phenylethynyl)indole-1-carboxylate；ethyl 2-(2-phenylethynyl)indole-1-carboxylate
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: APPMKRAXADBXGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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 2-(phenylethynyl)-1H-indole-1-carboxylate 在 甲醇 、 Au(JohnPhos)NTf₂ 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.5h， 生成 4-methyl-N-(2-phenyl-2-(2-(phenylethynyl)-1H-indol-3-yl)ethyl)benzenesulfonamide
  参考文献：
  名称：

  在氮丙啶与吲哚的开环反应中 利用阳离子金（i）催化剂的σ-亲性质†

  摘要：

  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。

  DOI：

  10.1039/c6ob00672h
• 作为产物：
  描述：

  ethyl 2-oxoindoline-1-carboxylate 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 ethyl 2-(phenylethynyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  2-Trifluoromethanesulfonyloxyindole-1-carboxylic Acid Ethyl Ester: A Practical Intermediate for the Synthesis of 2-Carbosubstituted Indoles

  摘要：

  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。

  DOI：

  10.1055/s-2005-918509

文献信息

• 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。
• Electrophile‐Promoted Nucleophilic Cyclization of 2‐Alkynylindoles to Give 4‐Substituted Oxazinoindolones
  作者：Guilherme Leonel、Isabella Klann、Davi F. Back、Bernardo A. Iglesias、Cristina W. Nogueira、Gilson Zeni

  DOI：10.1002/chem.202202847

  日期：2023.2.7

  AbstractA method for the synthesis of 4‐organoselanyl oxazinoindolone derivatives by the cascade cyclization of N‐(alkoxycarbonyl)‐2‐alkynylindoles using iron(III) chloride and diorganyl diselenides as promoters was developed. This protocol was applied to a series of N‐(alkoxycarbonyl)‐2‐alkynylindoles containing different substituents. The reaction conditions also tolerated a variety of diorganyl diselenides having both electron donating and electron withdrawing groups. However, the reaction did not work for diorganyl disulfides and ditellurides. The reaction mechanism seems to proceed via an ionic pathway and the cooperative action between iron(III) chloride and diorganyl diselenides is crucial for successful cyclization. We also found that using the same starting materials, by simply changing the electrophilic source to iodine, led to the formation of 4‐iodo‐oxazinoindolones. The high reactivity of Csp2−Se and Csp2−I bonds were tested under cross‐coupling conditions leading to the preparation of a new class of functionalized indole derivatives. In addition, the absorption, emission and electrochemical properties of 4‐organoselanyl oxazinoindolones showed an important relationship with the substituents of the aromatic rings. The advantages of the methodology include the use of electrophilic to promote the cyclization reaction and functionalization of the indole ring, and the electronic properties presented by the prepared compounds can be exploited as probes, analyte detectors and optical materials.