2,2,2-trifluoro-N-[2-[2-(4-phenylcyclohexen-1-yl)ethynyl]phenyl]acetamide | 143360-92-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2,2-trifluoro-N-[2-[2-(4-phenylcyclohexen-1-yl)ethynyl]phenyl]acetamide
• CAS: 143360-92-3
• 化学式: C₂₂H₁₈F₃NO
• 分子量: 369.386
• InChiKey: DLKHTNPNDSZQRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-喹啉基)甲胺 、 2,2,2-trifluoro-N-[2-[2-(4-phenylcyclohexen-1-yl)ethynyl]phenyl]acetamide 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三苯胂 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以40%的产率得到2-[2-(4-phenylcyclohex-1-en-1-yl)-1H-indol-3-yl]cyclohex-2-en-1-one
  参考文献：
  名称：

  3-(2-Alken-1-one-2-yl)indoles through the palladium-catalyzed reaction of 2-alkynyltrifluoroacetanilides with cyclic α-iodoenones

  摘要：

  alpha-Iodoenones can be efficiently employed as organic electrophiles in the Pd-catalyzed synthesis of 2, 3-disubstituted indoles from 2-alkynyltrifluoroacetanilides. Best results were obtained using the weak ligand As(Ph)(3). The methodology reported provides an efficient entry to indoles bearing a 2-alkenon-2-yl moiety linked in the 3-position, that possesses a scarcely reported substitution pattern. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.096
• 作为产物：
  描述：

  2-[(三甲基甲硅烷基)乙炔基]苯胺 在 四(三苯基膦)钯 potassium fluoride 、 copper(l) iodide 、 2,6-二叔丁基-4-甲基吡啶 、 二乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2,2,2-trifluoro-N-[2-[2-(4-phenylcyclohexen-1-yl)ethynyl]phenyl]acetamide
  参考文献：
  名称：

  A versatile approach to 2,3-disubstituted indoles through the palladium-catalysed cyclization of o-alkynyltrifluoroacetanilides with vinyl triflates and aryl halides.

  摘要：

  DOI：

  10.1016/s0040-4039(00)74818-0

文献信息

• <b>Preparation of Indoles from </b> <b><i>o</i></b> <b>-Alkynyltrifluoroacetanilides Through the Aminopalladation­-Reductive Elimination Process</b>
  作者：Sandro Cacchi、Giancarlo Fabrizi、Luca Parisi

  DOI：10.1055/s-2004-815993

  日期：——

  The functionalized pyrrole nucleus contained in the indole system has been assembled via the palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with organic halides/triflates or allyl carbonates. In the presence of carbon monoxide, a three-component reaction can take place and indole derivatives incorporating a molecule of carbon monoxide have been obtained.

  吲哚体系中所含的官能化吡咯核通过邻炔基三氟乙酰苯胺与有机卤化物/三氟甲磺酸酯或碳酸烯丙酯的钯催化反应组装而成。在一氧化碳存在的情况下，可以发生三组分反应，并获得掺入一氧化碳分子的吲哚衍生物。
• 2-Substituted 3-arylindoles through palladium-catalyzed arylative cyclization of 2-alkynyltrifluoroacetanilides with arylboronic acids under oxidative conditions
  作者：Antonio Arcadi、Sandro Cacchi、Giancarlo Fabrizi、Antonella Goggiamani、Antonia Iazzetti、Fabio Marinelli

  DOI：10.1039/c2ob27125g

  日期：——

  Free NH 2-substituted 3-arylindoles have been prepared usually in good to high yields through the palladium-catalyzed reaction of readily available 2-alkynyltrifluoroacetanilides with arylboronic acids under oxidative conditions. The reaction tolerates a variety of useful functional groups both in the arylboronic acid and in the alkyne, including chloro, formyl, and ester groups.

  通常通过在氧化条件下，易于获得的2-炔丙基三氟乙酰胺与芳基硼酸在钯催化下的反应，以良好至高产率制备了自由的NH 2-取代的3-芳基吲哚。该反应能够容忍芳基硼酸和炔烃中的多种有用官能团，包括氯、醛和酯基团。
• Arcadi, Antonio; Cacchi, Sandro; Fabrizi, Giancarlo, Synlett, 2000, # 3, p. 394 - 396
  作者：Arcadi, Antonio、Cacchi, Sandro、Fabrizi, Giancarlo、Marinelli, Fabio

  DOI：——

  日期：——