2'-fluoro-4-styrylpyridine | 389084-05-3

• 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: 2'-fluoro-4-styrylpyridine
• 英文别名: 4-[2-(2-Fluorophenyl)ethenyl]pyridine
• CAS: 389084-05-3
• 化学式: C₁₃H₁₀FN
• 分子量: 199.228
• InChiKey: WNDNWQJFFMVEOP-UHFFFAOYSA-N

物化性质

• 沸点：
  308.4±11.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2'-fluoro-4-styrylpyridine 在 potassium sulfide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以94%的产率得到4-(benzo[b]thiophen-2-yl)pyridine
  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'-fluoro-4-styrylpyridine
  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

• [2+2] Photodimerization of Stilbazoles Promoted by Oxalic Acid in Suspension
  作者：Thanh Binh Nguyen、Tuan Minh Nguyen、Pascal Retailleau

  DOI：10.1002/chem.201905597

  日期：2020.4.9

  waxy or even insoluble stilbazoles. Moreover, the oxalic acid loading could be lowered to sub-stoichiometric amounts. When further optimizations were needed, our strategy was found to be highly flexible to identify other oligocarboxylic acids as alternative additive to improve or even overturn regioselectivity. Oxalic acid and other oligocarboxylic acids were found to be capable of orienting more than

  在这项研究中，我们报道了一种非常简单的技术，可以有效地对某些乙烯基吡啶进行光二聚化。通过用几种苯乙烯基唑与分散在非极性（例如环己烷）或中等极性（苯，二氯甲烷，二恶烷）溶剂中的固体草酸二水合物的搅拌混合物进行辐照，可以高收率获得相应的二聚环丁烷加合物，具有极好的区域选择性。和立体选择性。该策略也可以成功地应用于油性，蜡质或什至不溶性斯蒂巴唑。此外，草酸负载量可降低至亚化学计量量。当需要进一步优化时，我们的策略非常灵活，可以确定其他低聚羧酸作为替代添加剂，从而改善甚至推翻区域选择性。
• Competition Between Head-to-Head and Head-to-Tail Photocycloaddition Reaction in the Solid State: A Case Study
  作者：Vaishali A. Sawant、Jien Wu、Jagdese J. Vittal

  DOI：10.1021/acs.cgd.8b00442

  日期：2018.6.6

  Solid state [2 + 2] cycloaddition photochemical reactions have recently emerged as a benign green method to synthesize cyclobutane derivatives. Synthesis of cyclobutane isomers are often controlled by the manner in which unsymmetrical olefin pairs have been aligned either in a head-to-head (HH) or head-to-tail (HT) manner using bridging ligands, organic templating agents, metalorganic clipping agents

  固态[2 + 2]环加成光化学反应最近作为合成环丁烷衍生物的良性绿色方法出现。环丁烷异构体的合成通常通过以下方式来控制：不对称烯烃对使用桥键式配体，有机模板剂，金属有机螯合剂以头对头（HH）或头对尾（HT）的方式进行排列和嗜金属相互作用。在这里，我们合成了三种Zn（II）一维配位聚合物（1D CPs），其中具有烯烃基的末端配体以HH和HT方式排列，并进行光环加成反应。其中，两个CP提供HH光产物，而第三CP提供HH和HT光产物的混合物。
• Solid‐State Photochemical [2+2] Cycloaddition Reaction of Mn ^II Complexes
  作者：Khushboo Yadava、Jagadese J. Vittal

  DOI：10.1002/chem.201901237

  日期：2019.8.6

  isomorphous and isostructural to 3. Complimentary π–π interactions in head‐to‐tail alignment of the styrylpyridine ligands furnishes 1D aggregates in 1–3 which are congenial to undergo [2+2] cycloaddition reaction under UV light. Whereas, face‐to‐face alignment of the 4spy pairs in 4 is expected to provide a head‐to‐head photoproduct. All the MnII complexes are indeed found to be photoreactive. To our surprise

  在相似的实验条件下合成了三种Mn II配合物。在这些[Mn 2（苯甲酸酯）4（L）2 ]中（其中L = 4-苯乙烯基吡啶或4spy，1和2-氟-4'-苯乙烯基吡啶或2F-4spy，3）是桨轮配合物，但在不同的空间中结晶组。[Mn 2（苯甲酸酯）4（3F-4spy）4 ]（3F-4spy = 3-氟-4'-苯乙烯基吡啶），而4是双核络合物，化学计量比不同于1和3，带有两对3F-4spy配体。面对面对齐。空间群发生不可逆的相变P 2 1 / ç到ç 2 / ç当1加热至125℃至2在单晶到单晶方式或时地面1至粉末。2对3是同构的，并且是同构的。在苯乙烯基吡啶配体的头-尾对准免费π-π相互作用配料在1D聚集体1 - 3，其是投机经历在UV光下的[2 + 2]环加成反应。鉴于4中的4个间谍对的面对面对齐可提供一对一的照相产品。所有Mn II确实发现复合物具有光反应性。令我们惊讶的是，与它们的Zn
• Multistimuli-Responsive Dynamic Effects in a One-Dimensional Coordination Polymer
  作者：Bibhuti Bhusan Rath、Mayank Gupta、Jagadese J. Vittal

  DOI：10.1021/acs.chemmater.1c03012

  日期：2022.1.11

  The development of multistimuli-receptive actuators demands a rational combination of suitable functionalities. Achieving such actuating properties in a single crystalline material is a challenge. In spite of several investigations on photo-, thermo,- and mechano-responsive crystals, single crystalline material displaying all these effects is rare. By a judicious combination of photoreactive 2-fluoro-4′-styrylpyridine units and flexible Pb3(SCN)3 units, a multistimuli-responsive one-dimensional (1D) coordination polymer (CP) showing all these dynamic effects has been fabricated. Single crystals of the CP display rapid ballistic events upon ultraviolet (UV) irradiation triggered by [2 + 2] cycloaddition of photoreactive ligands. In addition, macroscopic jumping, bending, and splitting of the crystals were observed during both heating and cooling cycles because of reversible phase transition. Further, slender crystals of the CP exhibit elastic deformation upon the application of mechanical force. With handful of examples of CPs show macroscopic dynamic effects, this CP paves the way for designing multistimuli-responsive multisalient actuating materials.

  开发多刺激感应致动器需要将合适的功能合理地结合在一起。在单晶材料中实现这种致动器特性是一项挑战。尽管对光响应、热响应和机械响应晶体进行了多项研究，但能显示所有这些效应的单晶体材料并不多见。通过将具有光活性的 2-氟-4′-苯乙烯吡啶单元和柔性 Pb3(SCN)3 单元巧妙地结合在一起，我们制造出了一种多刺激响应的一维配位聚合物（CP），它能显示出所有这些动态效应。该配位聚合物的单晶体在光活性配体的[2 + 2]环加成引发的紫外线（UV）照射下显示出快速弹道事件。此外，在加热和冷却循环过程中，由于可逆相变，还观察到晶体的宏观跳跃、弯曲和分裂。此外，当施加机械力时，CP 的细长晶体会发生弹性变形。有了少量显示出宏观动态效应的 CP 例子，这种 CP 为设计多刺激响应多梯度致动材料铺平了道路。
• Single Crystals Popping Under UV Light: A Photosalient Effect Triggered by a [2+2] Cycloaddition Reaction
  作者：Raghavender Medishetty、Ahmad Husain、Zhaozhi Bai、Tomče Runčevski、Robert E. Dinnebier、Panče Naumov、Jagadese J. Vittal

  DOI：10.1002/anie.201402040

  日期：2014.6.2

  level. Here, we report the first example of a photosalient effect (photoinduced leaping) observed with crystals of three coordination complexes which is induced by a [2+2] photocycloaddition reaction. Unlike a plethora of other dimerization reactions, when exposed to even weak UV light, single crystals of these materials burst violently, whereby they are propelled to travel several millimeters. The results

  动态单晶的极为罕见的例子，其中光或热的激发引起宏观运动，这不仅是分子材料将能量转换为功的效用的视觉上引人注目的演示，而且还为探索之间的机械联系提供了独特的机会。宏观上的集体分子过程及其后果。在这里，我们报告的第一个例子是由[2 + 2]光环加成反应诱导的三个配位配合物晶体观察到的光敏效应（光诱导跃迁）。与大量其他二聚反应不同，当暴露于弱紫外光时，这些材料的单晶会剧烈破裂，从而被推动移动几毫米。