2-fluorostilbene | 64345-69-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-fluorostilbene
• 英文别名: 1-(o-Fluorphenyl)-2-phenylaethen；Fluorostilbene；1-fluoro-2-(2-phenylethenyl)benzene
• CAS: 64345-69-3
• 化学式: C₁₄H₁₁F
• 分子量: 198.24
• InChiKey: FMGVTMQBJISCFC-UHFFFAOYSA-N

物化性质

• 沸点：
  287.3±15.0 °C(Predicted)
• 密度：
  1.120±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：
  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：
  1

反应信息

• 作为反应物：
  描述：

  2-fluorostilbene 在 potassium sulfide 、 重水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以92%的产率得到2-phenylbenzo[b]thiophene-d
  参考文献：
  名称：

  Transition-Metal-Free Method for the Synthesis of Benzo[b]thiophenes from o-Halovinylbenzenes and K2S via Direct SNAr-Type Reaction, Cyclization, and Dehydrogenation Process

  摘要：

  A new, highly efficient procedure for the synthesis of benzothiophenes from easily available o-halovinylbenzenes and potassium sulfide has been developed. The reaction tolerated a wide range of functionalities, and various 2-substituted benzo[b]thiophenes are provided in the high yields in the absence of a transition-metal catalyst.

  DOI：

  10.1055/s-0033-1339289
• 作为产物：
  描述：

  2-氟溴苄 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 11.0h， 生成 2-fluorostilbene
  参考文献：
  名称：

  Transition-Metal-Free Method for the Synthesis of Benzo[b]thiophenes from o-Halovinylbenzenes and K2S via Direct SNAr-Type Reaction, Cyclization, and Dehydrogenation Process

  摘要：

  A new, highly efficient procedure for the synthesis of benzothiophenes from easily available o-halovinylbenzenes and potassium sulfide has been developed. The reaction tolerated a wide range of functionalities, and various 2-substituted benzo[b]thiophenes are provided in the high yields in the absence of a transition-metal catalyst.

  DOI：

  10.1055/s-0033-1339289

文献信息

• Easy-separable magnetic nanoparticle-supported Pd catalysts: Kinetics, stability and catalyst re-use
  作者：Urszula Laska、Christopher G. Frost、Gareth J. Price、Pawel K. Plucinski

  DOI：10.1016/j.jcat.2009.10.001

  日期：2009.12.10

  novel palladium-based catalysts supported on magnetic nanoparticles with diameters of 7–17 nm have been prepared and evaluated in C–C coupling, hydrogenation and amination reactions. One type of catalyst used palladium complexes containing phosphine and/or acetate ligands for applications in Suzuki and Heck reactions. The second type consisted of Pd(0)-functionalised magnetic cores for use in hydrogenation

  制备了一系列新型的钯基催化剂，负载在直径7至17 nm的磁性纳米粒子上，并进行了C-C偶联，加氢和胺化反应的评估。一种类型的催化剂使用包含膦和/或乙酸酯配体的钯配合物，用于Suzuki和Heck反应。第二种类型是用于氢化和CC偶联的Pd（0）-官能化磁芯。每种类型对一系列反应均有效，并且由于载体的超顺磁性行为，很容易从反应混合物中回收。进行了详细的速率研究，发现其与拟一级动力学相对应，以帮助确定反应机理，结果表明，在Heck反应过程中，Pd浸出关键取决于芳基卤化物的存在。
• Ruthenium-Catalyzed Oxidation of Alkenes at Room Temperature: A Practical and Concise Approach to α-Diketones
  作者：Shulin Chen、Zhaojun Liu、Erbo Shi、Long Chen、Wei Wei、Hong Li、Yannan Cheng、Xiaobing Wan

  DOI：10.1021/ol200716d

  日期：2011.5.6

  The catalytic oxidation of alkenes to α-diketones is unprecedented. A new oxidation of alkenes, catalyzed by a ruthenium complex, which allows an efficient route to α-diketones using TBHP as an oxidant is described. This methodology is highly functional group tolerant, is practically convenient, requires no additional ligand, and operates under mild conditions with short reaction times. Based upon

  烯烃催化氧化为α-二酮是前所未有的。描述了一种新的由钌配合物催化的烯烃氧化，可使用TBHP作为氧化剂有效地合成α-二酮。该方法具有高度的官能团耐受性，实用方便，不需要额外的配体，并且可在温和条件下以较短的反应时间运行。基于实验观察，提出了一个合理的机制。
• Ligand- and copper-free Sonogashira and Heck couplings of (Het)aryl chlorides and bromides catalyzed by palladium nanoparticles supported on in situ generated Al(OH)₃
  作者：Xing Li、Xiaolei Gong、Zhipeng Li、Honghong Chang、Wenchao Gao、Wenlong Wei

  DOI：10.1039/c6ra25416k

  日期：——

  ligand- and copper-free Sonogashira reaction of (Het)aryl halides (Br and Cl) with various terminal alkynes and the Heck coupling of (Het)aryl halides (Br and Cl) with a series of olefins, catalyzed by palladium nanoparticles supported on newly generated Al(OH)3, were developed. The catalyst can be readily recovered and reused 6 times without significant loss of activity and palladium leaching.

  （Het）芳基卤化物（Br和Cl）与各种末端炔烃的无配体和无铜Sonogashira反应以及（Het）芳基卤化物（Br和Cl）与一系列烯烃的Heck偶联，负载的钯纳米粒子在新生成的Al（OH）3上进行了研究。该催化剂可以容易地回收并重复使用6次，而不会显着降低活性和钯的浸出。
• Pd(II)-catalyzed oxidative Heck-type reaction of triarylphosphines with alkenes via carbon–phosphorus bond cleavage
  作者：Ming-Tao Ma、Jian-Mei Lu

  DOI：10.1016/j.tet.2013.01.025

  日期：2013.3

  A Pd(II)-catalyzed oxidative Heck-type reaction of triarylphosphines with alkenes via carbon–phosphorus bond cleavage was reported. Under the optimal reaction conditions, most reactions proceeded smoothly to give the expected coupling products in acceptable to high yields.

  据报道，通过碳-磷键裂解，Pd（II）催化三芳基膦与烯烃的氧化Heck型反应。在最佳反应条件下，大多数反应进行顺利，从而以可接受的产率获得了预期的偶联产物。
• Photocyclodehydrofluorination
  作者：Zhe Li、Robert J. Twieg

  DOI：10.1002/chem.201502473

  日期：2015.10.26

  undergo ring closure and HF is eliminated. This photocyclodehydrofluorination (PCDHF) reaction is very useful to produce a wide range of selectively fluorinated polynuclear aromatic hydrocarbons that possess a phenanthrene (or heterocyclic analogue of phenanthrene) substructure. These fluorinated products are of great interest in various aspects of the materials science.

  Mallory型光环化涉及一系列的对苯二酚，邻-三联苯和相关衍生物的光反应，这些反应通过二氢菲中间体进行分子内环化。在典型的Mallory光环化反应中，通常需要氧化剂才能产生最终的含菲产品。在这里描述的研究中，适当的氟化苯乙烯和邻-叔苯基会闭环并消除HF。该光环脱氢氟化（PCDHF）反应对于生产范围广泛的具有菲（或菲的杂环类似物）亚结构的选择性氟化多核芳香烃非常有用。这些氟化产品在材料科学的各个方面都引起了极大的兴趣。