1-bromo-3-(3,3,3-trifluoroprop-1-yn-1-yl)benzene | 7119-08-6

• 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: 1-bromo-3-(3,3,3-trifluoroprop-1-yn-1-yl)benzene
• 英文别名: 1-bromo-3-(3,3,3-trifluoroprop-1-ynyl)benzene
• CAS: 7119-08-6
• 化学式: C₉H₄BrF₃
• 分子量: 249.03
• InChiKey: KRVBEDRXHHEUCC-UHFFFAOYSA-N

物化性质

• 沸点：
  122-123 °C(Press: 75 Torr)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-bromo-3-(3,3,3-trifluoroprop-1-yn-1-yl)benzene 在 lithium iodide 作用下， 以 溶剂黄146 为溶剂， 反应 16.0h， 以78%的产率得到(E)-1-iodo-1-(3-bromophenyl)-3,3,3-trifluoropropene
  参考文献：
  名称：

  Regio- and stereo-specific preparation of (E)-1-aryl-3,3,3-trifluoro-1-iodo-propenes and their palladium-catalyzed reaction with terminal alkynes

  摘要：

  A new type of iodo-containing trifluoromethylated building blocks were synthesized. The reaction of 1-aryl-3,3,3-trifluoropropynes 1 with lithium iodide in acetic acid at 75 degrees C gave (E)-1-aryl-3,3,3-trifluoro-1-iodo-propenes 2 in high yield, which undergo the palladium-catalyzed Sonogashira reaction with terminal alkynes afforded trifluoromethyl-containing 1,3-enynes in high yield. (c) 2008 Published by Elsevier B.V.

  DOI：

  10.1016/j.jfluchem.2008.01.002
• 作为产物：
  描述：

  1-溴-3-碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 copper(l) iodide 、 1,10-菲罗啉 、 二异丙胺 、 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 1-bromo-3-(3,3,3-trifluoroprop-1-yn-1-yl)benzene
  参考文献：
  名称：

  在室温下用Me 3 SiCF 3进行Cu（I）/ Ag（I）介导的芳基丙酸的脱羧三氟甲基化反应

  摘要：

  已经开发了一种新型的Cu（I）/ Ag（I）介导的Me 3 SiCF 3芳基丙酸脱羧三氟甲基化反应，用于在温和条件下构建Csp-CF 3键。该方法在室温下平稳进行并显示出广泛的功能相容性，以高收率提供了一系列相应的含三氟甲基化乙炔基的芳族化合物。

  DOI：

  10.1016/j.tet.2016.05.012

文献信息

• Iron-Catalyzed Intermolecular Hydrothiolation of Internal Alkynes with Thiosalicylic Acids, and Sequential Intramolecular Cyclization Reaction
  作者：Taro Sonehara、Shogo Murakami、Sae Yamazaki、Motoi Kawatsura

  DOI：10.1021/acs.orglett.7b01953

  日期：2017.8.18

  We demonstrate the iron-catalyzed intermolecular coupling of internal alkynes and thiosalicylic acid derivatives. The reaction was effectively catalyzed by the Fe(acac)2/1,10-phenanthroline catalyst in toluene/HFIP (hexafluoroisopropyl alcohol) as the reaction solvent and afforded several types of 1,3-oxathiine derivatives in moderate to high yields through the intermolecular hydrothiolation and sequential

  我们证明了内部炔烃和硫代水杨酸衍生物的铁催化的分子间偶联。Fe（acac）2 / 1,10-菲咯啉催化剂在甲苯/ HFIP（六氟异丙醇）中作为反应溶剂有效地催化了该反应，并通过分子间反应以中等至高收率提供了几种类型的1,3-氧代嘧啶衍生物氢硫基化和顺序分子内环化。
• Iridium-Catalyzed Regioselective Synthesis of Trifluoromethylated Isocoumarins through Annulation of Benzoic Acids with Trifluoromethylated Alkynes
  作者：Guangyuan Liu、Guanghua Kuang、Xingxing Zhang、Naihao Lu、Yang Fu、Yiyuan Peng、Yirong Zhou

  DOI：10.1021/acs.orglett.9b00572

  日期：2019.5.3

  An unprecedented Ir-catalyzed oxidative coupling of benzoic acids with trifluoromethylated alkynes was successfully developed to provide diverse trifluoromethylated isocoumarins in moderate to good yields. This new practical procedure was highlighted by mild reaction conditions, broad substrate scope, good regioselectivity, high efficiency, and easy operation.

  成功开发出前所未有的Ir催化的苯甲酸与三氟甲基化炔烃的氧化偶合，以中等到良好的产率提供各种三氟甲基化异香豆素。反应条件温和，底物范围广，区域选择性好，效率高且易于操作，突出了这一新的实用程序。
• Synthesis of trifluoromethyl-group-containing cyclopentadienones by the palladium-catalyzed [2 + 2 + 1] cycloaddition of aryl- and trifluoromethyl-group substituted internal alkynes and carbon monoxide
  作者：Shogo Murakami、Taro Sonehara、Kousuke Iwakami、Hiroaki Tsuji、Motoi Kawatsura

  DOI：10.1016/j.tetlet.2019.01.036

  日期：2019.2

  We investigated the palladium-catalyzed [2 + 2 + 1] cycloaddition of aryl- and trifluoromethyl-group-substituted internal alkynes and carbon monoxide, and revealed that the PdBr2 effectively catalyzed the intended reaction. The PdBr2-catalyzed reaction smoothly proceeded and provided aryl- and trifluoromethyl-group-containing cyclopentadienone derivatives in up to 92% yield.

  我们研究了钯催化的芳基和三氟甲基取代的内部炔烃和一氧化碳的[2 + 2 + 1]环加成反应，并揭示了PdBr 2有效催化了预期的反应。PdBr 2催化的反应顺利进行，并以高达92％的收率提供了含芳基和三氟甲基的环戊二烯酮衍生物。
• Copper-Catalyzed Defluorinative Thioannulation of Trifluoropropynes for the Synthesis of 1,2-Dithiole-3-thiones
  作者：Feng Wei、Xiao-Qin Shen、Xiao-Hong Zhang、Xing-Guo Zhang

  DOI：10.1002/adsc.201800846

  日期：2018.10.18

  A simple and practical strategy for the preparation of 1,2‐dithiole‐3‐thiones via copper‐catalyzed defluorinative thioannulation of trifluoropropynes has been developed using elemental sulfur as the sole sulfur source. This reaction displays a wide substrate scope and high functional group tolerance to afford the corresponding S‐heterocycles in moderate to good yields and features efficient construction

  通过元素硫作为唯一的硫源，开发了一种简单实用的方法，该方法通过铜催化的三氟丙炔的脱氟硫代环化反应制备1,2-二硫代3-硫酮。该反应显示出较宽的底物范围和较高的官能团耐受性，能够以中等至良好的产率提供相应的S-杂环，并具有通过CF 3基团的CF键断裂有效构建多个CS键的特征。
• Trifluoromethylated Indolopyranones through Regioselective Annulation of Indole Carboxylic Acids with Unsymmetric Internal Trifluoromethylated Alkynes
  作者：Xingxing Zhang、Guangyuan Liu、Yiyuan Peng、Hua Li、Yirong Zhou

  DOI：10.1002/ejoc.202200658

  日期：2022.8.26

  Three in one: three valid pharmacophores (indole, pyranone and trifluoromethyl) were successfully combined into one molecule by rhodium-catalyzed regioselective annulation of indole carboxylic acids with unsymmetric internal trifluoromethylated alkynes.

  三合一：通过铑催化的吲哚羧酸与不对称的内部三氟甲基化炔烃的区域选择性环化，三种有效的药效团（吲哚、吡喃酮和三氟甲基）成功地结合成一个分子。