1-氟-2-[2-(4-氟苯基)乙炔基]苯 | 148004-79-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-氟-2-[2-(4-氟苯基)乙炔基]苯
• 英文名称: 1-fluoro-2-((4-fluorophenyl)ethynyl)benzene
• 英文别名: 1-Fluoro-2-[(4-fluorophenyl)ethynyl]benzene；1-fluoro-2-[2-(4-fluorophenyl)ethynyl]benzene
• CAS: 148004-79-9
• 化学式: C₁₄H₈F₂
• 分子量: 214.214
• InChiKey: ZAELEDXBGNMOFS-UHFFFAOYSA-N

物化性质

• 沸点：
  298.0±25.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-氟-2-[2-(4-氟苯基)乙炔基]苯 在 二硫化碳 、 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 24.0h， 以61%的产率得到2-(4-fluorophenyl)benzo[b]thiophene
  参考文献：
  名称：

  三硫代碳酸根阴离子作为硫源，用于合成2,5-二取代的噻吩和2-取代的苯并[b]噻吩。

  摘要：

  通过简单的方法，由CS 2和KOH在二甲基亚砜中原位生成三硫代碳酸根阴离子（CS 3 2-），并用作S 2-合成子的新型合成等价物，用于由1合成2，5-二取代的噻吩。 ，3-丁二炔。另外，该体系用于由2-卤代炔基（杂）芳烃的无金属合成2-取代的苯并[ b ]噻吩。这些化合物是从廉价且容易获得的硫源中获得的，具有中等至良好的收率，并具有良好的官能团耐受性。

  DOI：

  10.1021/acs.joc.0c01516
• 作为产物：
  描述：

  4-氟苯基溴化镁 在 四(三苯基膦)钯 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 36.33h， 生成 1-氟-2-[2-(4-氟苯基)乙炔基]苯
  参考文献：
  名称：

  由1-溴炔烃与有机烷烃试剂的交叉偶联反应高效合成1,2-二取代的乙炔衍生物

  摘要：

  通过在温和条件下钯催化的炔基卤化物与（杂）芳基铝试剂的交叉偶联，已开发出一种高效的合成1,2-二取代乙炔衍生物的途径。这使得相应的交叉耦合产品具有高达99％的优良分离产率。在炔基卤化物或芳基铝基质中带有给电子或吸电子基团的芳基产生了良好的交联产物收率。此过程简单易行，为合成1,2-二取代的乙炔衍生物提供了一种有效的方法。根据实验结果，提出了可能的催化循环。

  DOI：

  10.1016/j.tet.2018.08.050

文献信息

• Highly efficient synthesis of 1,2-disubstituted acetylenes derivatives from the cross-coupling reactions of 1-bromoalkynes with organotitanium reagents
  作者：Chuan Wu、Qing-Han Li

  DOI：10.1016/j.tet.2021.132370

  日期：2021.9

  A Highly efficient route for the synthesis of 1,2-disubstituted acetylene derivatives has been developed by nickel catalyzed cross-couplings of alkynyl halides with aryl titanium reagents under mild conditions. This has given corresponding cross-coupling products good to excellent isolated yields of up to 92 %. The aryls bearing electron-donating or electron-withdrawing groups in either alkynylhalides

  通过在温和条件下炔基卤化物与芳基钛试剂的镍催化交叉偶联，开发了一种高效合成 1,2-二取代乙炔衍生物的途径。这使得相应的交叉偶联产品具有高达 92% 的优良分离产率。在炔基卤化物或芳基钛底物中带有给电子或吸电子基团的芳基产生了良好的交叉偶联产物。该过程简单易行，为合成1,2-二取代乙炔衍生物提供了一种有效的方法。
• Nucleophilic displacement of fluorine from fluorodiarylacetylenes by alkoxide and phenoxide
  作者：Martino Paventi、Allan S. Hay

  DOI：10.1016/s0040-4039(00)77475-2

  日期：1993.2

  Difluoroarylacetylenes synthesized in dimethylformamide in the presence of potassium tert-butoxide from flourobenzyl-1H(or 2H)benzotriazoles and N-flourophenylmethyleneanilines, undergo facile displacement of flourine by tert-butoxide and phenoxide.

  在叔丁醇钾存在下，由氟苄基-1 H（或2 H）苯并三唑和N-氟苯基亚甲基苯胺在二甲基甲酰胺中合成的二氟芳基乙炔，可通过叔丁醇和苯酚方便地置换。
• Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[<i>b</i>]furans and benzo[<i>b</i>]thiophenes
  作者：Yibiao Li、Liang Cheng、Xiaohang Liu、Bin Li、Ning Sun

  DOI：10.3762/bjoc.10.305

  日期：——

  reaction and its application in the synthesis of benzo[b]furan and benzo[b]thiophene derivatives is presented starting from readily available 2-fluorophenylacetylene derivatives. The key annulation step involves the hydration of the C-F bond of 2-fluorophenylacetylene derivatives followed by an intramolecular annulation to afford benzo[b]furan and benzo[b]thiophene derivatives. Moreover, structurally important

  从容易获得的2-氟苯基乙炔衍生物开始，提出了一种有效的铜促进的水合反应及其在苯并[b]呋喃和苯并[b]噻吩衍生物的合成中的应用。关键的环合步骤涉及2-氟苯基乙炔衍生物的CF键的水合，然后进行分子内环合，得到苯并[b]呋喃和苯并[b]噻吩衍生物。而且，以良好的产率提供了结构上重要的2，2′-双苯并呋喃支架。
• Aryl alkynylation versus alkyne homocoupling: unprecedented selectivity switch in Cu, phosphine and solvent-free heterogeneous Pd-catalysed couplings
  作者：Marco Bandini、Rafael Luque、Vitaly Budarin、Duncan J. Macquarrie

  DOI：10.1016/j.tet.2005.06.082

  日期：2005.10

  Sonogashira reaction and oxidative dimerisation of terminal alkynes are among the most relevant and attractive C-C bond forming transformations in the metallo-catalysed cross-coupling scenario. Often, the homocoupling reactions of substituted acetylenic derivatives are concomitant to the Sonogashira pathway and time-consuming optimization procedures are required in order to reach satisfactory levels of selectivity. In this paper, the potential of a class of Pd-complexes loaded to mesoporous silica gel in promoting the Sonogashira reaction between aryl acetylenes and iodoarenes is underlined. This family of heterogeneous organo-palladium systems allows the desired cross-coupled compounds to be isolated in excellent yield under very mild conditions. In fact, the absence of organic solvents, copper(I) co-catalyst and phosphane ligands, (which are easily oxidisable and whose preparation has a heavy environmental impact), in conjunction with the low catalyst loading ([Pd] 0.1-1 mol%) and its recoverability, stresses the environmental benefits of the protocol. The Sonogashira/homocoupling selectivity proved to be function of the haloarene employed. As a matter of fact, while iodoarenes bearing EWG (electron withdrawing groups) on the phenyl ring underwent smoothly the Sonogashira pathway, electron-rich iodobenzenes showed opposite behaviour by mainly furnishing the homocoupling product. The use of bromoarenes provided solely the homocoupling product in excellent yield without themselves being consumed. This is despite that fact that the catalysts used activate bromoarenes equally as well as iodoarenes in both Heck and Suzuki systems. Kinetic investigations revealed a highly temperature-dependent profile, which indicates strongly that the reaction takes place at the surface. Finally, the full heterogeneous character of the catalytically active species as well as the reusability of the immobilised Pd-complex were confirmed by hot-filtration test and by multiple reuses of the supported catalyst in subsequent Sonogashira cross-couplings. (c) 2005 Elsevier Ltd. All rights reserved.
• US5233046A
  申请人：——

  公开号：US5233046A

  公开（公告）日：1993-08-03