1-methyl-2-(3,3,3-trifluoroprop-1-ynyl)benzene | 1378520-32-1

• 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-methyl-2-(3,3,3-trifluoroprop-1-ynyl)benzene
• 英文别名: 1-methyl-2-(3,3,3-trifluoroprop-1-yn-1-yl)benzene；1-Methyl-2-(3,3,3-trifluoro-1-propynyl)benzene
• CAS: 1378520-32-1
• 化学式: C₁₀H₇F₃
• 分子量: 184.161
• InChiKey: MQELTMAEBKFZSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  165.9±40.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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-methyl-2-(3,3,3-trifluoroprop-1-ynyl)benzene 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 四甲基乙二胺 、 caesium carbonate 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以75%的产率得到5-(o-tolyl)-3H-1,2-dithiole-3-thione
  参考文献：
  名称：

  铜催化的三氟丙炔脱氟硫代环化反应合成1,2-二硫代3-硫酮

  摘要：

  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。

  DOI：

  10.1002/adsc.201800846
• 作为产物：
  描述：

  2-乙炔基甲苯 在 叔丁基过氧化氢 、 正丁基锂 、 碳酸氢钠 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 1-methyl-2-(3,3,3-trifluoroprop-1-ynyl)benzene
  参考文献：
  名称：

  Copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with Langlois' reagent

  摘要：

  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.

  DOI：

  10.1016/j.tet.2014.02.005

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。
• Synthesis of Trifluoromethyl-Substituted Ethyl Picolinate Derivatives by the Cobalt-Catalyzed Regioselective Intermolecular [2+2+2] Cycloaddition
  作者：Motoi Kawatsura、Tomoki Ishikawa、Taro Sonehara、Shogo Murakami、Maki Minakawa

  DOI：10.1055/s-0035-1562432

  日期：——

  We demonstrated the intermolecular [2+2+2] cycloaddition of aryl- and trifluoromethyl-substituted internal alkyne and ethyl cyano­formate, and succeeded in constructing the pyridine derivatives using the CoI 2 /dcype/Zn catalyst system. The reaction proceeded with a high regioselectivity, and two trifluoromethyl-substituted ethyl picolinate derivatives were obtained as a single regioisomer.

  我们展示了芳基-和三氟甲基-取代的内炔和氰基甲酸乙酯的分子间[2+2+2]环加成，并成功地使用CoI 2 /dcype/Zn催化剂体系构建了吡啶衍生物。该反应以高区域选择性进行，并以单一区域异构体的形式获得了两种三氟甲基取代的吡啶甲酸乙酯衍生物。
• 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.