((4-fluorophenyl)ethynyl)(trifluoromethyl)sulfane | 1388753-65-8

• 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: ((4-fluorophenyl)ethynyl)(trifluoromethyl)sulfane
• 英文别名: 1-Fluoro-4-[2-(trifluoromethylsulfanyl)ethynyl]benzene；1-fluoro-4-[2-(trifluoromethylsulfanyl)ethynyl]benzene
• CAS: 1388753-65-8
• 化学式: C₉H₄F₄S
• 分子量: 220.19
• InChiKey: YIFOEIXTNBZYNH-UHFFFAOYSA-N

物化性质

• 沸点：
  160.3±50.0 °C(predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  异戊醛 、 ((4-fluorophenyl)ethynyl)(trifluoromethyl)sulfane 在 tetrakis(tetrabutylammonium)decatungstate(VI) 作用下， 以 水 、 乙腈 为溶剂， 以53 %的产率得到3-(4-fluorophenyl)-4,4-dimethyl-2-((trifluoromethyl)thio)cyclopentan-1-one
  参考文献：
  名称：

  10.1002/anie.202407689

  摘要：

  A photocatalyzed formal (3+2) cycloaddition has been developed to construct original polysubstituted α‐SCF3 cyclopentanones in a regio‐ and diastereoselective manner. This building block approach leverages trifluoromethylthio alkynes and branched / linear aldehydes, as readily available reaction partners, in consecutive hydrogen atom transfers and C–C bond formations. Difluoromethylthio alkynes are also compatible subtrates. Furthermore, the potential for telescoped reaction starting from alcohols instead of aldehydes was demonstrated, as well as process automatization and scale‐up under continuous microflow conditions. This prompted density functional theory calculations to support a free radical‐mediated cascade hydrogen atom transfer process.

  DOI：

  10.1002/anie.202407689
• 作为产物：
  描述：

  4-氟苯乙炔 在 N-溴代丁二酰亚胺(NBS) 、 silver hexafluoroantimonate 、 chloro[di(1-adamantyl)-2-dimethylaminophenylphosphine]gold(I) 、 silver nitrate 作用下， 以 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 18.0h， 生成 ((4-fluorophenyl)ethynyl)(trifluoromethyl)sulfane
  参考文献：
  名称：

  金 (I/III) 催化的有机卤化物的三氟甲硫基化和三氟甲基硒化

  摘要：

  报道了第一个金（I/III）催化的有机卤化物的直接三氟甲硫基化和三氟甲基硒化。这种温和高效的方案具有广泛的底物范围和高产量（> 60 个示例，分离产量高达 97%）。各种生物活性分子的后期功能化证明了其稳健性，这使得该反应适用于制药和农用化学品的研究和开发。

  DOI：

  10.1002/anie.202115687

文献信息

• Metal-Free Oxidative Trifluoromethylthiolation of Terminal Alkynes with CF₃SiMe₃ and Elemental Sulfur
  作者：Chao Chen、Lingling Chu、Feng-Ling Qing

  DOI：10.1021/ja305801m

  日期：2012.8.1

  A metal-free oxidative trifluoromethyl-thiolation of terminal alkynes using readily available CF(3)SiMe(3) and elemental sulfur at room temperature has been developed. This reaction provides an efficient and convenient method for the preparation of alkynyl trifluoromethyl sulfides bearing a wide range of functional groups. Preliminary investigation revealed that elemental sulfur instead of air acted

  已经开发出在室温下使用现成的 CF(3)SiMe(3) 和元素硫对末端炔烃进行无金属氧化三氟甲基硫醇化。该反应为制备具有广泛官能团的炔基三氟甲基硫化物提供了一种高效便捷的方法。初步调查显示元素硫代替空气充当氧化剂。
• Oxidative Trifluoromethylthiolation of Terminal Alkynes with AgSCF₃: A Convenient Approach to Alkynyl Trifluoromethyl Sulfides
  作者：Sheng-Qing Zhu、Xiu-Hua Xu、Feng-Ling Qing

  DOI：10.1002/ejoc.201402533

  日期：2014.7

  new method for the efficient synthesis of alkynyl trifluoromethyl sulfides was developed. By combining AgSCF3 and NCS in N,N-dimethylacetamide, an electrophilic active intermediate was produced, which was then treated with a variety of terminal alkynes to afford the corresponding trifluoromethanesulfenylated products in moderate to excellent yields.

  开发了一种高效合成炔基三氟甲基硫化物的新方法。通过在 N,N-二甲基乙酰胺中结合 AgSCF3 和 NCS，产生了亲电活性中间体，然后用各种末端炔烃处理，以中等至极好的收率提供相应的三氟甲磺酰化产物。
• A concise synthesis of (alkynyl)(trifluoromethyl)sulfanes via a bismuth(<scp>iii</scp>)-promoted reaction of trimethyl(alkynyl)silane with trifluoromethanesulfanylamide
  作者：Jie Sheng、Jie Wu

  DOI：10.1039/c4ob01451k

  日期：——

  A bismuth(III)-promoted reaction of trimethyl(alkynyl)silanes with trifluoromethanesulfanylamide is developed, giving rise to (alkynyl)(trifluoromethyl)sulfanes in good yields.

  开发了一种铋(III)促进的反应，将三甲基(炔基)硅烷与三氟甲烷磺酰胺反应，生成(炔基)(三氟甲基)硫醇，产率良好。
• Ligand-Controlled Regiodivergent Alkoxycarbonylation of Trifluoromethylthiolated Internal Alkynes
  作者：Bin Wang、Chaoren Shen、Kaiwu Dong

  DOI：10.1021/acs.orglett.4c01113

  日期：2024.5.3

  Controlling the regioselectivity for the alkoxycarbonylation of unsymmetric internal alkynes is challenging. Herein, a palladium-catalyzed ligand-controlled regiodivergent alkoxycarbonylation of internal trifluoromethylthiolated alkynes was achieved. A series of α- or β-SCF3 acrylates from the same trifluoromethylthiolated alkyne were obtained with moderate to high yield and regioselectivity.

  控制不对称内炔烷氧基羰基化的区域选择性具有挑战性。在此，实现了内部三氟甲基硫醇炔烃的钯催化配体控制的区域发散烷氧基羰基化。由相同的三氟甲硫醇炔获得了一系列α-或β-SCF 3丙烯酸酯，具有中等到高产率和区域选择性。