N-(2-((2-bromophenyl)ethynyl)phenyl)-2,2,2-trifluoroacetamide

• 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: N-(2-((2-bromophenyl)ethynyl)phenyl)-2,2,2-trifluoroacetamide
• 英文别名: N-{2-[(2-bromophenyl)ethynyl]phenyl}-2,2,2-trifluoroacetamide；N-[2-[2-(2-bromophenyl)ethynyl]phenyl]-2,2,2-trifluoroacetamide
• 化学式: C₁₆H₉BrF₃NO
• 分子量: 368.153
• InChiKey: GDVLFMBWRDEBSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  N-(2-((2-bromophenyl)ethynyl)phenyl)-2,2,2-trifluoroacetamide 在 四(三苯基膦)钯 、 四丁基氟化铵 、 cesium acetate 、 palladium diacetate 、 sodium hydride 、 caesium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 9.0h， 生成 9H-二苯并[A,C]咔唑
  参考文献：
  名称：

  二苯并[一，Ç ]咔唑由2-（2-溴代）-3- arylindoles通过钯催化的分子内C-H官能化/ C-C键的形成过程†

  摘要：

  2-（2-溴芳基）-3-芳基吲哚的钯催化环化为二苯并[ a，c ]咔唑提供了一种新的通用方法。该反应可耐受多种有用的取代基，包括氯，硝基，醚，氰基，酮基和酯基。

  DOI：

  10.1039/c2ob26741a
• 作为产物：
  描述：

  2-((2-bromophenyl)ethynyl)aniline 、 三氟乙酸酐 在 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(2-((2-bromophenyl)ethynyl)phenyl)-2,2,2-trifluoroacetamide
  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

文献信息

• 2,3-Disubstituted Indoles via Palladium-Catalyzed Reaction of 2-Alkynyltrifluoroacetanilides with Arenediazonium Tetrafluoroborates
  作者：Sandro Cacchi、Giancarlo Fabrizi、Antonella Goggiamani、Alcide Perboni、Alessio Sferrazza、Paolo Stabile

  DOI：10.1021/ol101321g

  日期：2010.7.16

  A novel palladium-catalyzed synthesis of free N−H 2,3-disubstituted indoles from arenediazonium tetrafluoroborates and 2-alkynyltrifluoroacetanilides is presented. The reaction tolerates a variety of useful substituents both in the starting alkyne and the arenediazonium salt, including bromo and chloro substituents, nitro, cyano, keto, ester, and ether groups, as well as ortho substituents such as

  提出了一种新颖的钯催化四氢硼酸芳族重氮鎓和2-炔基三氟乙酰苯胺合成游离NH 2，3-二取代的吲哚的方法。该反应可耐受起始炔烃和芳二氮杂鎓盐中的多种有用的取代基，包括溴和氯取代基，硝基，氰基，酮基，酯和醚基，以及邻位取代基如甲氧基和甲基。
• Palladium-Catalyzed Cyclization of <i>o</i>-Alkynyltrifluoroacetanilides with Allyl Esters. A Regioselective Synthesis of 3-Allylindoles
  作者：Sandro Cacchi、Giancarlo Fabrizi、Paola Pace

  DOI：10.1021/jo971237p

  日期：1998.2.1

  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.
• 2-Aryl and 2-Heteroaryl Indoles from 1-Alkynes and <i>o</i>-Iodotrifluoroacetanilide through a Domino Copper-Catalyzed Coupling−Cyclization Process
  作者：Sandro Cacchi、Giancarlo Fabrizi、Luca M. Parisi

  DOI：10.1021/ol035378r

  日期：2003.10.1

  [GRAPHICS]A general method for the synthesis of 2-aryl and 2-heteroaryl indoles from aryl iodides and 1-alkynes through a domino copper-catalyzed process is reported. The best results have been obtained with [Cu(phen)(PPh3)(2)]NO3 in the presence of K3PO4 in toluene or dioxane at 110 degreesC. 2-Aryl and 2-heteroaryl indoles can also be isolated in good yields by using catalysts derived from CuI and PPh3 in dioxane at 110 degreesC.
• 3-(2-Alken-1-one-2-yl)indoles through the palladium-catalyzed reaction of 2-alkynyltrifluoroacetanilides with cyclic α-iodoenones
  作者：Antonio Arcadi、Roberto Cianci、Giovanni Ferrara、Fabio Marinelli

  DOI：10.1016/j.tet.2010.01.096

  日期：2010.3

  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.
• Dibenzo[a,c]carbazoles from 2-(2-bromoaryl)-3-arylindoles via a palladium-catalyzed intramolecular C–H functionalization/C–C bond formation process
  作者：Sandro Cacchi、Giancarlo Fabrizi、Antonella Goggiamani、Antonia Iazzetti

  DOI：10.1039/c2ob26741a

  日期：——

  The palladium-catalyzed cyclization of 2-(2-bromoaryl)-3-arylindoles provides a new versatile approach to dibenzo[a,c]carbazoles. The reaction tolerates a variety of useful substituents including chloro, nitro, ether, cyano, keto, and ester groups.

  2-（2-溴芳基）-3-芳基吲哚的钯催化环化为二苯并[ a，c ]咔唑提供了一种新的通用方法。该反应可耐受多种有用的取代基，包括氯，硝基，醚，氰基，酮基和酯基。