1,1,1-trifluoro-6-phenyl-2-hexyne | 686350-30-1

• 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: 1,1,1-trifluoro-6-phenyl-2-hexyne
• 英文别名: (6,6,6-trifluorohex-4-ynyl)benzene；6,6,6-Trifluorohex-4-ynylbenzene
• CAS: 686350-30-1
• 化学式: C₁₂H₁₁F₃
• 分子量: 212.215
• InChiKey: SKEQAHGLFCFYHG-UHFFFAOYSA-N

物化性质

• 沸点：
  219.2±40.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (E)-N-(2-iodobenzylidene)-2-methylpropan-2-amine 、 1,1,1-trifluoro-6-phenyl-2-hexyne 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以15%的产率得到3-(3-phenylpropyl)-4-trifluoromethylisoquinoline
  参考文献：
  名称：

  Regioselective One-Step Synthesis of 4-Fluoroalkylated Isoquinolines via Carbopalladation Reaction of Fluorine-Containing Alkynes

  摘要：

  The palladium-catalyzed annulation reaction of fluoroalkylated alkynes with various 2-iodobenzylidenamines was investigated. In the presence of a catalytic amount of Pd-(PPh3)(4), the reaction took place smoothly to give the corresponding 4-fluoroalkylated isoquinoline in high yield as a single isomer. No other regioisomer was detected.

  DOI：

  10.1021/jo051700v
• 作为产物：
  描述：

  4,4,4-trifluoro-1-(2-phenylethyl)-2-butynyl acetate 在 dicobalt octacarbonyl 、 三氟甲磺酸三甲基硅酯 、 三正丁基氢锡 、 ferric nitrate 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以41%的产率得到1,1,1-trifluoro-6-phenyl-2-hexyne
  参考文献：
  名称：

  基于尼古拉斯反应的含氟炔属化合物的新型合成方法

  摘要：

  由γ-氟烷基化的炔丙基乙酸酯和Co 2（CO）8制备的含氟二钴六羰基配合物在炔丙基位置与各种亲核试剂平稳反应，然后在Fe（NO 3）3的作用下氧化分解，得到具有良好至高产率的带有各种类型的烷基侧链的氟代烷基炔烃。

  DOI：

  10.1016/j.jfluchem.2005.11.009

文献信息

• Cu(I)/Ag(I)-mediated decarboxylative trifluoromethylation of arylpropiolic acids with Me 3 SiCF 3 at room temperature
  作者：Lingling Yang、Linlin Jiang、Yaming Li、Xinmei Fu、Rong Zhang、Kun Jin、Chunying Duan

  DOI：10.1016/j.tet.2016.05.012

  日期：2016.7

  A novel Cu(I)/Ag(I)-mediated decarboxylative trifluoromethylation of arylpropiolic acids with Me3SiCF3 has been developed for the construction of Csp-CF3 bond under mild conditions. This method proceeds smoothly at room temperature and shows a widely functional compatibility, providing a series of corresponding trifluoromethylated acetylenyl-containing aromatics in good yields.

  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。
• 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。
• Remarkable access to fluoroalkylated trisubstituted alkenes via highly stereoselective cobalt-catalyzed hydrosilylation reaction of fluoroalkylated alkynes
  作者：Tsutomu Konno、Ken-ichi Taku、Shigeyuki Yamada、Kazuki Moriyasu、Takashi Ishihara

  DOI：10.1039/b819476a

  日期：——

  Hydrosilylation reaction of various fluoroalkylated alkynes with Et3SiH in the presence of a catalytic amount of Co2(CO)8 was investigated. The hydrosilylation of the alkynes having fluoroalkyl and aryl groups took place smoothly with good regioselectivity (ca. 80:20). In sharp contrast, the reaction of the alkynes having a fluoroalkyl group and a benzyl-type substituent, or various propargyl alcohols gave the corresponding vinylsilanes in an excellent regio- and stereoselective manner. Treatment of the vinylsilanes with various aldehydes in the presence of Zn(OTf)2 and TBAF afforded the coupling products in good yields.

  在催化剂 Co2(CO)8 的存在下，研究了各种氟烷基炔烃与 Et3SiH 的氢硅化反应。具有氟烷基和芳基的炔烃顺利发生了氢硅烷化反应，且具有良好的区域选择性（约为 80:20）。与此形成鲜明对比的是，具有氟烷基和苄基取代基的炔烃或各种丙炔醇以极好的区域和立体选择性反应生成相应的乙烯基硅烷。在 Zn(OTf)2 和 TBAF 的存在下，用各种醛处理乙烯基硅烷，可以得到产率很高的偶联产物。
• A Facile Synthesis of Various Fluorine-Containing Indole Derivatives via Palladium-Catalyzed Annulation of Internal Alkynes
  作者：Jungha Chae、Tsutomu Konno、Takashi Ishihara、Hiroki Yamanaka

  DOI：10.1246/cl.2004.314

  日期：2004.3

  The palladium-catalyzed annulation reaction of a variety of fluorine-containing internal alkynes with 2-iodoaniline derivatives took place smoothly to give the corresponding 2,3-disubstituted indol...

  钯催化的各种含氟内炔与2-碘苯胺衍生物的环化反应顺利进行，得到相应的2,3-二取代吲哚...
• A Facile Regiocontrol in the Palladium-Catalyzed Annulation of Fluorine-Containing Internal Alkynes with Variously Substituted 2-Iodoanilines:  A New Regioselective Synthesis of 2- or 3-Fluoroalkylated Indole Derivatives
  作者：Tsutomu Konno、Jungha Chae、Takashi Ishihara、Hiroki Yamanaka

  DOI：10.1021/jo048872x

  日期：2004.11.1

  Treatment of various types of fluoroalkylated alkynes with o-iodoaniline in the presence of Pd(PPh3)4 in DMF at 80 °C for 8 h mainly gave 2-fluoroalkylated indoles in high yields. The use of P(o-Tol)3 instead of PPh3 as a ligand led to the preferential formation of 3-fluoroalkylated indoles in high yields. Interestingly, the reaction of trifluoromethylated alkynes bearing a benzylic substituent afforded

  在Pd（PPh 3）4的存在下，在DMF中于80°C用邻碘苯胺处理各种类型的氟代烷基化炔烃，主要以高收率得到2-氟代烷基化的吲哚。使用P（邻-Tol）3代替PPh 3作为配体导致高产率优先形成3-氟烷基化的吲哚。有趣的是，带有苄基取代基的三氟甲基化炔烃的反应以良好的产率提供了2-或3-三氟乙基化的吲哚衍生物。