3-(3,3,3-trifluoroprop-1-yn-1-yl)thiophene | 136000-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-(3,3,3-trifluoroprop-1-yn-1-yl)thiophene
• 英文别名: 3-(3,3,3-Trifluoroprop-1-ynyl)thiophene
• CAS: 136000-17-4
• 化学式: C₇H₃F₃S
• 分子量: 176.162
• InChiKey: KEDRHHUIFDTILR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-chloro-4,4,4-trifluoro-2-thiophen-3-ylbut-2-enal 在 氢氧化钾 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以75%的产率得到3-(3,3,3-trifluoroprop-1-yn-1-yl)thiophene
  参考文献：
  名称：

  Synthesis of trifluoromethylalkenes and alkynes. Trifluoromethyl captodative olefins

  摘要：

  beta-ethylthio-beta-trifluoromethylketones 3 and aldehydes 4 are easily prepared from beta-chloroolefines 5 and 6. Trifluoromethylalkynes 7 and captodative alkenes 8 are obtained by reaction of KOH on aldehydes 6 or 4.

  DOI：

  10.1016/0040-4039(91)80692-y

文献信息

• Copper-Mediated Aerobic Oxidative Trifluoromethylation of Terminal Alkynes with Me₃SiCF₃
  作者：Lingling Chu、Feng-Ling Qing

  DOI：10.1021/ja102175w

  日期：2010.6.2

  An efficient copper-mediated trifluoromethylation of terminal alkynes with nucleophilic trifluoromethylating reagent (Me(3)SiCF(3)) was developed. Both aromatic alkynes and aliphatic alkynes were effective, and a variety of functionalities such as amino, -OMe, -CO(2)Et, -Br, and -NO(2) were tolerated under the reaction conditions. This reaction provides a general, straightforward, and practically useful

  开发了一种有效的铜介导的末端炔烃与亲核三氟甲基化试剂 (Me(3)SiCF(3)) 的三氟甲基化。芳香族炔烃和脂肪族炔烃都是有效的，并且在反应条件下可以容忍各种官能团，例如氨基、-OMe、-CO(2)Et、-Br 和-NO(2)。该反应为制备三氟甲基化乙炔提供了一种通用、直接且实用的方法。
• An Organocopper(III) Fluoride Triggering C−CF₃ Bond Formation
  作者：Daniel Joven‐Sancho、Andrea Echeverri、Nathalie Saffon‐Merceron、Julia Contreras‐García、Noel Nebra

  DOI：10.1002/anie.202319412

  日期：2024.3.11

  The first organocopper(III) fluoride, [PPh4][CuIII(CF3)3F] (2), has been isolated and authenticated. Despite its stability, 2 reacts with alkynylsilanes leading to industrially relevant trifluoromethylalkynes (RC≡CCF3). Mechanistic investigations, including the trapping of [PPh4][CuIII(CF3)3(C≡CPh)] (4a), validates the operability of a CuI/CuIII redox shuttle in oxidative C−C couplings occurring through

  第一种氟化有机铜(III) [PPh 4 ][Cu III (CF 3 ) 3 F] ( 2 ) 已被分离和鉴定。尽管具有稳定性， 2仍会与炔基硅烷发生反应，生成工业相关的三氟甲基炔烃 (RC≡CCF 3 )。机理研究，包括捕获 [PPh 4 ][Cu III (CF 3 ) 3 (CQICPh)] ( 4 a )，验证了 Cu I /Cu III氧化还原穿梭在氧化 C−C 偶联中的可操作性迄今为止难以捉摸的有机铜(III)氟化物。
• Fluoroform-Derived CuCF₃ for Trifluoromethylation of Terminal and TMS-Protected Alkynes
  作者：Lisi He、Gavin Chit Tsui

  DOI：10.1021/acs.orglett.6b00999

  日期：2016.6.17

  An efficient trifluoromethylation reaction of alkynes using a fluoroform-derived CuCF3 reagent is described. The CF3 source is the inexpensive industrial waste fluoroform (CF3H). The air-stable CuCF3 reagent can be prepared in large quantities and is convenient to use. Synthetically useful trifluoromethylated alkynes containing a wide range of functional groups were successfully synthesized under mild conditions. Both terminal and TMS-protected alkynes gave the products in one step. The beneficial effect of a diamine ligand tetramethylethylenediamine (TMEDA) with the fluoroform-derived CuCF3 reagent was also demonstrated.
• Copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with Langlois' reagent
  作者：Srinivas Reddy Dubbaka、Shashidhar Nizalapur、Azmi Reddy Atthunuri、Manohar Salla、Thresen Mathew

  DOI：10.1016/j.tet.2014.02.005

  日期：2014.3

  Synthesis of trifluoromethylated acetylenes by copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with CF3 radicals generated from NaSO2CF3 and tert-butyl hydroperoxide (TBHP) is communicated. The trifluoromethylated acetylenes were obtained in good to moderate yields. The presented method tolerates a wide range of aromatic, heteroaromatic, and aliphatic potassium alkynyltrifluoroborates. (C) 2014 Elsevier Ltd. All rights reserved.