o-[(p-Acetylphenyl)ethynyl]trifluoroacetanilide | 201813-48-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: o-[(p-Acetylphenyl)ethynyl]trifluoroacetanilide
• 英文别名: N-(2-((4-acetylphenyl)ethynyl)phenyl)-2,2,2-trifluoroacetamide；N-[2-[2-(4-acetylphenyl)ethynyl]phenyl]-2,2,2-trifluoroacetamide
• CAS: 201813-48-1
• 化学式: C₁₈H₁₂F₃NO₂
• 分子量: 331.294
• InChiKey: JIQZGWCFXXUEAD-UHFFFAOYSA-N

物化性质

• 熔点：
  141-142 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• 沸点：
  473.4±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  o-[(p-Acetylphenyl)ethynyl]trifluoroacetanilide 在 四(三苯基膦)钯 caesium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 丙酮 、 乙腈 为溶剂， 反应 23.0h， 生成 1-[2-(4-Acetyl-phenyl)-1H-indol-3-yl]-2-phenyl-ethanone
  参考文献：
  名称：

  Palladium-Catalyzed Reaction of o-Alkynyltrifluoroacetanilides with 1-Bromoalkynes. An Approach to 2-Substituted 3-Alkynylindoles and 2-Substituted 3-Acylindoles

  摘要：

  The palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes affords free N-H 2-substituted 3-alkynylindoles in satisfactory to high yield. 2-Substituted 3-alkynylindoles revealed useful intermediates for the regioselective synthesis of 2-substituted 3-acylindoles. The latter can be prepared from o-alkynyltrifluoroacetanilides and 1-bromoalkynes via a one-pot cyclization-hydration protocol, omitting the isolation of 2-substituted 3-alkynylindoles.

  DOI：

  10.1021/jo050517z
• 作为产物：
  描述：

  2-[(三甲基甲硅烷基)乙炔基]苯胺 在 copper(l) iodide 、 bis(triphenylphosphine) palladium (Il) acetate 、 potassium carbonate 、 二乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 o-[(p-Acetylphenyl)ethynyl]trifluoroacetanilide
  参考文献：
  名称：

  Palladium-Catalyzed Cyclization of o-Alkynyltrifluoroacetanilides with Allyl Esters. A Regioselective Synthesis of 3-Allylindoles

  摘要：

  The reaction of readily available o-alkynyltrifluoroacetanilides 1 with allyl esters provides a valuable new route to 3-allylindoles 3. Three basic procedures have been developed: a stepwise method based on the isolation of the N-allyl derivative 4 and its subsequent cyclization to 3 (procedure a), a one-pot reaction omitting the isolation of 4 (procedure b), and a procedure which most probably leads to the formation of 3 through a mechanism not involving the intermediacy of 4 (procedure c). In the presence of the electron-rich sterically encumbered ligand tris(2,4,6-trimethoxyphenyl)phosphine (ttmpp) the reaction exhibits remarkable regioselectivity and almost exclusive formation of 3-allylindoles with the indolyl moiety bound to the less substituted allyl terminus is usually observed. However, some loss of olefin geometry is observed.

  DOI：

  10.1021/jo971237p

文献信息

• Palladium-catalyzed cyclization of o-alkynyltrifluoroacetanilides followed by isocyanide insertion: synthesis of 2-substituted 1H-indole-3-carboxamides
  作者：Ziwei Hu、Dongdong Liang、Jiaji Zhao、Jinbo Huang、Qiang Zhu

  DOI：10.1039/c2cc33435f

  日期：——

  A base-controlled synthesis of 2-substituted secondary and tertiary 1H-indole-3-carboxamides through PdCl2-catalyzed cyclization of o-alkynyltrifluoroacetanilides followed by isocyanide insertion has been developed. The reaction proceeds smoothly at ambient temperature using O2 in air as the sole oxidant of the palladium catalyst.

  开发了一种通过PdCl2催化的o-炔基三氟乙酰苯胺的环化反应，随后进行异氰化物插入，合成2-取代的二级和三级1H-吲哚-3-羧酰胺的基控合成方法。在室温下，使用空气中的O2作为钯催化剂的唯一氧化剂，反应顺利进行。
• 2,3-Disubstituted Indoles through the Palladium-Catalyzed Reaction of Aryl Chlorides witho-Alkynyltrifluoroacetanilides
  作者：Sandro Cacchi、Giancarlo Fabrizi、Antonella Goggiamani

  DOI：10.1002/adsc.200606060

  日期：2006.7

  2,3-Disubstituted indoles can be prepared in moderate to excellent yields by reacting readily available o-alkynyltrifluoroacetanilides with aryl chlorides in MeCN at 120 °C in the presence of Pd2(dba)3 and Xphos.

  在Pd 2（dba）3和Xphos的存在下，使易获得的邻炔基三氟乙酰苯胺与芳基氯在MeCN中在120°C下反应，可以以中等至优异的产率制备2,3-二取代的吲哚。
• <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。
• 2-Substituted 3-Aryl- and 3-Heteroarylindoles by the Palladium-Catalyzed Reaction of<i>o</i>-Trifluoroacetanilides with Aryl Bromides and Triflates.
  作者：Sandro Cacchi、Giancarlo Fabrizi、Doriano Lamba、Fabio Marinelli、Luca M. Parisi

  DOI：10.1055/s-2003-38079

  日期：——

  The palladium-catalyzed reaction of aryl and heteroaryl bromides and triflates with o-alkynyltrifluoroacetanilides affords 2-substituted 3-aryl- and heteroarylindoles usually in excellent yield. The procedure can be applied to the synthesis of 2-substituted indole-3-carboxaldehydes.

  芳基和杂芳基溴化物和三氟甲磺酸酯与邻炔基三氟乙酰苯胺的钯催化反应通常以优异的收率得到 2-取代的 3-芳基和杂芳基吲哚。该程序可应用于2-取代吲哚-3-甲醛的合成。