o-ethynyltrifluoroacetanilide | 143360-93-4

• 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: o-ethynyltrifluoroacetanilide
• 英文别名: 2,2,2-Trifluoro-N-(2-ethynylphenyl)acetamide；N-(2-ethynylphenyl)-2,2,2-trifluoroacetamide
• CAS: 143360-93-4
• 化学式: C₁₀H₆F₃NO
• 分子量: 213.159
• InChiKey: KCMMJPYCTNJPQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  o-ethynyltrifluoroacetanilide 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以80%的产率得到吲哚
  参考文献：
  名称：

  3-Aryl-2-Unsubstituted Indoles through the Palladium-Catalysed Reaction of o-Ethynyltrifluoroacetanilide with Aryl Iodides

  摘要：

  易得的o-乙炔基三氟乙酰苯胺与芳基碘化物在催化量Pd2dba3和过量K2CO3的存在下，在DMSO中于40°C反应，提供了良产率的2-未取代-3-芳基吲哚。将o-乙炔基三氟乙酰苯胺在没有芳基碘化物的相同反应条件下进行反应，则能高产率地生成吲哚。

  DOI：

  10.1055/s-1997-1039
• 作为产物：
  描述：

  2,2,2-trifluoro-N-(2-iodophenyl)acetamide 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 o-ethynyltrifluoroacetanilide
  参考文献：
  名称：

  Solid-Phase Syntheses of Furopyridine and Furoquinoline Systems

  摘要：

  Syntheses of 2-substituted furo[3,2-b]pyridines and furo[3,2-h]quinolines have been achieved for the first time in the solid-phase mode. The central enabling steps involved concomitant deprotection/cyclization promoted by the mild base K2CO3. Reactions were monitored "in situ" in real time by a variety of spectroscopic techniques, which allowed full and accurate control of progress in these syntheses.

  DOI：

  10.1021/ol049762f

文献信息

• Electrochemical Difluoromethylarylation of Alkynes
  作者：Peng Xiong、He-Huan Xu、Jinshuai Song、Hai-Chao Xu

  DOI：10.1021/jacs.8b00391

  日期：2018.2.21

  unprecedented radical difluoromethylarylation reaction of alkynes has been developed by discovering a new difluoromethylation reagent, CF2HSO2NHNHBoc. This air-stable and solid reagent can be prepared in one step from commercially available reagents CF2HSO2Cl and NH2NHBoc. The CF2H radical, generated through ferrocene-mediated electrochemical oxidation, participates in an unexplored alkyne addition reaction

  通过发现一种新的二氟甲基化试剂 CF2HSO2NHNHBoc，开发了一种前所未有的炔烃自由基二氟甲基芳基化反应。这种空气稳定的固体试剂可以由市售试剂 CF2HSO2Cl 和 NH2NHBoc 一步制备。通过二茂铁介导的电化学氧化产生的 CF2H 自由基参与未探索的炔加成反应，然后是具有挑战性的 7 元环形成均裂芳烃取代步骤，以提供氟化二苯并氮杂。
• Palladium-Catalyzed Cyclization of <i>N</i>-Acyl-<i>o</i>-alkynylanilines with Isocyanides Involving a 1,3-Acyl Migration: Rapid Access to Functionalized 2-Aminoquinolines
  作者：Meng Li、Jia Zheng、Weigao Hu、Chunsheng Li、Jianxiao Li、Songjia Fang、Huanfeng Jiang、Wanqing Wu

  DOI：10.1021/acs.orglett.8b03165

  日期：2018.11.16

  the synthesis of functionalized 2-aminoquinolines via palladium-catalyzed annulation of N-acyl-o-alkynylanilines with isocyanides has been developed with high atom economy, in which an unconventional 6-endo-dig cyclization process is observed. Further investigations of the mechanism demonstrated that an intramolecular acyl migration of the N-protecting groups was involved in this transformation.

  通过钯催化的环为官能化2-氨基喹啉的合成的简单和有利的办法Ñ -acyl- ö与异氰化物-alkynylanilines研制了具有高的原子经济性，在这种非常规的6-内-挖观察到环化方法。对该机理的进一步研究表明，N-保护基团的分子内酰基迁移与该转化有关。
• Fused bicycloheterocycle substituted quinuclidine derivatives
  申请人：Ji Jianguo

  公开号：US20050137204A1

  公开（公告）日：2005-06-23

  Compounds of formula (I) wherein n is 0, 1, or 2; A is N or N + —O − ; X is O, S, —NH—, and —N-alkyl-; Ar 1 is a 6-membered aromatic ring; and Ar 2 is a fused bicycloheterocycle. The compounds are useful in treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands. Also disclosed are pharmaceutical compositions having compounds of formula (I) and methods for using such compounds and compositions.

  式(I)的化合物，其中n为0、1或2；A为N或N+—O−；X为O、S、—NH—和—N-烷基-；Ar1为6-成员芳香环；Ar2为融合的双环杂环。这些化合物在治疗α7 nAChR配体预防或改善的病症或疾病中很有用。还公开了具有式(I)化合物的药物组合物以及使用这些化合物和组合物的方法。
• [EN] NOVEL COMPOUND, PREPARATION METHOD THEREOF, AND USE THEREOF<br/>[FR] NOUVEAU COMPOSÉ, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION
  申请人：DAEGU GYEONGBUK MEDICAL INNOVATION FOUND

  公开号：WO2021145729A1

  公开（公告）日：2021-07-22

  The present invention relates to a method for preparing a biomaterial having selectively functionalized tyrosine, a biomaterial having selectively functionalized tyrosine, and a pharmaceutical composition containing the same as an active ingredient. The method for preparing a biomaterial to which a compound represented by formula 2 is coupled, of the present invention, allows the compound represented by formula 2 to be selectively coupled, in a high yield in a biomaterial, to tyrosine, which is present on the surface of an aqueous solution such that the coupling thereof to amino acids other than tyrosine does not occur and, when only one tyrosine is present, heterogeneous mixtures are not present and the inherent activity of the biomaterial is maintained, and thus the compound can be effectively used as a pharmaceutical composition containing a biomaterial drug as an active ingredient. In addition, the method can selectively functionalize tyrosine, and thus can be effectively used for tyrosine functionalization in a biomaterial.

  本发明涉及一种制备具有选择性功能化酪氨酸的生物材料的方法，具有选择性功能化酪氨酸的生物材料，以及含有该生物材料作为活性成分的药物组合物。本发明的一种制备生物材料的方法，其中将由式2表示的化合物偶联到生物材料，使得该化合物能够选择性地偶联到酪氨酸，且在生物材料中的产率较高，酪氨酸位于水溶液表面，使得其与酪氨酸以外的氨基酸不发生偶联，当只有一个酪氨酸存在时，不会出现异质混合物，同时保持生物材料的固有活性，因此该化合物可以有效地用作含有生物材料药物的药物组合物的活性成分。此外，该方法可以选择性功能化酪氨酸，因此可以有效地用于生物材料中的酪氨酸功能化。
• 2-Substituted-3-acylindoles through the Palladium-Catalysed Carbonylative Cyclization of 2-Alkynyltrifluoroacetanilides with Aryl Halides and Vinyl Triflates
  作者：Antonio Arcadi、Sandro Cacchi、Veronica Carnicelli、Fabio Marinelli

  DOI：10.1016/s0040-4020(01)80766-3

  日期：1994.1

  The palladium-catalysed reaction of readily accessible 2-alkynyltrifluoroacetanilides with aryl hanides and vinyl triflates under a carbon monoxide atmosphere (1 or 7 atm) the presence of potassium carbonate produce s 2-substituted-3-acyl indoles in fair to good yield. The acidity of the nitrogen-hydrogen bond proved to be of primary importance for the success of the reaction. The methodology has been

  在碳酸钾的存在下，在一氧化碳气氛（1或7 atm）下，钯易于催化的2-炔基三氟乙酰苯胺与芳基化物和乙烯基三氟甲磺酸酯的反应，可公平地以良好的收率产生s 2-取代的3-酰基吲哚。事实证明，氮氢键的酸度对于反应的成功至关重要。该方法已被用于合成普鲁瓦多林，该药物对人的术后疼痛具有镇痛作用。