1,1,1-trifluoro-2-nonyne

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 1,1,1-trifluoro-2-nonyne
• 英文别名: hexyltrifluoromethylacetylene；1,1,1-trifluoronon-2-yne；1,1,1-Trifluoronon-2-yne
• 化学式: C₉H₁₃F₃
• 分子量: 178.197
• InChiKey: MBJNVNNWANDMHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  硫代水杨酸 、 1,1,1-trifluoro-2-nonyne 在 1,10-菲罗啉 、 iron(II) acetylacetonate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以79%的产率得到2-hexyl-2-(2,2,2-trifluoroethyl)-4H-benzo[d][1,3]oxathiin-4-one
  参考文献：
  名称：

  铁催化内部炔烃与硫代水杨酸的分子间氢硫醇化反应以及顺序的分子内环化反应

  摘要：

  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。

  DOI：

  10.1021/acs.orglett.7b01953
• 作为产物：
  描述：

  铜(I)己基乙炔化物 、 (三氟甲基)三甲基硅烷 在 四甲基乙二胺 作用下， 以 N,N-二甲基甲酰胺 、 Petroleum ether 为溶剂， 反应 24.0h， 以59%的产率得到1,1,1-trifluoro-2-nonyne
  参考文献：
  名称：

  合成三氟甲基化炔烃的实用方法：乙炔铜和炔烃的氧化三氟甲基化

  摘要：

  报道了两种实用和互补的方法用于合成三氟甲基化炔烃。第一种是混合搅拌法，基于易得的和板凳稳定的乙炔铜的氧化三氟甲基化，而第二种基于较广泛的底物范围，并且与现有方法相比具有多个优点，其基础是末端炔烃的氧化铜催化直接三氟甲基化。两种反应均提供了用户友好的三氟甲基化乙炔的合成方法，该方法可轻松地从容易获得的起始原料中获得。

  DOI：

  10.1002/adsc.201400057

文献信息

• First practical synthesis of 2- or 3-fluoroalkylated indenols via cobalt-catalyzed [2 + 3] carbocyclization of fluorine-containing alkynes and 2-iodoaryl ketones
  作者：Tatsuya Kumon、Kazuhiro Yoshida、Shigeyuki Yamada、Tomohiro Agou、Toshio Kubota、Tsutomu Konno

  DOI：10.1016/j.tet.2019.05.042

  日期：2019.7

  [2 + 3] Cycloaddition reaction of fluorine-containing alkynes with various 2-iodoaryl ketones in the presence of CoCl2(dppf) catalyst proceeded very smoothly to give the corresponding 2- or 3-fluoroalkylated indenols in 57–98% yields. These regioisomers could be successfully separated and obtained in a pure form. From X-ray crystallographic and NOESY analyses, major or minor regioisomers were determined

  [2 + 3]在CoCl 2（dppf）催化剂存在下，含氟炔烃与各种2-碘代芳基酮的环加成反应非常顺利，以57-98％的收率得到了相应的2-或3-氟代烷基化的茚基。这些区域异构体可以成功地分离并以纯净形式获得。从X射线晶体学和NOESY分析，主要或次要区域异构体分别确定为3-或2-氟代烷基化的茚基。
• A Copper(I)-Catalyzed Addition/Annulation Sequence for the Two-Component Synthesis of γ-Ylidenebutenolides
  作者：Sangwon Seo、Michael C. Willis

  DOI：10.1021/acs.orglett.7b02151

  日期：2017.9.1

  A highly efficient Cu(I)-catalyzed addition/annulation sequence has been developed for the synthesis of (Z)-ylidenebutenolides employing readily available alpha-ketoacids and alkynes as substrates. The reactions employ a simple commercially available Cu(I)-catalyst, display good substrate scope, and deliver products with high stereoselectivity. The synthetic utility of the method is demonstrated by the straightforward derivatization of the ylidenebutenolides into a diverse range of heterocycles, and also by the preparation of the natural product bovolide, and analogs thereof.
• Facile syntheses of various per- or polyfluoroalkylated internal acetylene derivatives
  作者：Tsutomu Konno、Jungha Chae、Masashi Kanda、Go Nagai、Kazushige Tamura、Takashi Ishihara、Hiroki Yamanaka

  DOI：10.1016/s0040-4020(03)01199-2

  日期：2003.9

  Treatment of per- or polyfluoroalkylated vinyl iodides 5 with 2 equiv. of n-BuLi in THF produced the corresponding lithium acetylides in situ, which were transformed into zinc acetylides by the addition of ZnCl2.TMEDA complex into the reaction mixture. The in situ generated zinc acetylides were exposed to the cross-coupling conditions such as ArI/cat. Pd(PPh3)(4), reflux, 6-12 h, giving rise to the desired per- or polyfluoroalkylated acetylenes in high yields. In the case of trifluoromethylated acetylene, commercially available 2-bromo-3,3,3-trifluoropropene 6 could also be used instead of 5 as the starting material. In the acetylenes having a fluoroalkyl group and an aliphatic side chain, vinyl iodides 7, prepared by radical addition of perfluoroalkyl iodide to terminal acetylenes, were treated with t-BuOK at room temperature or at the reflux temperature of benzene, affording the desired compounds in good yields. (C) 2003 Elsevier Ltd. All rights reserved.
• Practical Methods for the Synthesis of Trifluoromethylated Alkynes: Oxidative Trifluoromethylation of Copper Acetylides and Alkynes
  作者：Cédric Tresse、Céline Guissart、Stéphane Schweizer、Yassine Bouhoute、Anne-Caroline Chany、Mary-Lorène Goddard、Nicolas Blanchard、Gwilherm Evano

  DOI：10.1002/adsc.201400057

  日期：2014.6.16

  Two practical and complementary methods are reported for the synthesis of trifluoromethylated alkynes. The first one, a mix‐and‐stir process, is based on the oxidative trifluoromethylation of readily available and bench‐stable copper acetylides while the second one, which displays a broad substrate scope and has several advantages over existing procedures, is based on the oxidative copper‐catalyzed

  报道了两种实用和互补的方法用于合成三氟甲基化炔烃。第一种是混合搅拌法，基于易得的和板凳稳定的乙炔铜的氧化三氟甲基化，而第二种基于较广泛的底物范围，并且与现有方法相比具有多个优点，其基础是末端炔烃的氧化铜催化直接三氟甲基化。两种反应均提供了用户友好的三氟甲基化乙炔的合成方法，该方法可轻松地从容易获得的起始原料中获得。
• 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。