2-氟吩嗪 | 397-57-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2-氟吩嗪
• 英文名称: 2-fluorophenazine
• 英文别名: 2-Fluor-phenazin
• CAS: 397-57-9
• 化学式: C₁₂H₇FN₂
• 分子量: 198.199
• InChiKey: IAGQFKKPPASHTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基吩嗪 在 tetrafluoroboric acid 、 sodium nitrite 作用下， 生成 2-氟吩嗪
  参考文献：
  名称：

  Tschernezkii et al., Zhurnal Obshchei Khimii, 1955, vol. 25, p. 2161,2167; engl. Ausg. S. 2123, 2128

  摘要：

  DOI：

文献信息

• Reactivity and substituent effects in the cyclization of N -aryl-2-nitrosoanilines to phenazines
  作者：Zbigniew Wróbel、Karolina Plichta、Andrzej Kwast

  DOI：10.1016/j.tet.2017.04.046

  日期：2017.6

  estimated on the base of the observed reaction times. A strong opposite effect of substituents located at position para to the nitroso group and those located para to the amino group in the side ring was observed. Mechanistic explanation, based on the electronic properties of the substituents and their mesomeric effects, was presented. The usefulness of the obtained data for the designed syntheses of

  根据观察到的反应时间，估算了在N，O-双（三甲基甲硅烷基）乙酰胺（BSA）存在下进行环化反应生成吩嗪衍生物的反应中，各种取代的N-芳基-2-亚硝基苯胺的反应活性。。观察到在侧环中位于亚硝基对位的取代基与位于氨基对位的取代基有强烈的相反作用。提出了基于取代基的电子性质及其介观效应的机理解释。公开了所获得的数据对于吩嗪的设计合成的有用性。
• An umpolung strategy for rapid access to thermally activated delayed fluorescence (TADF) materials based on phenazine
  作者：Huaxing Zhang、Qiang Guo、Hu Cheng、Chunhao Ran、Di Wu、Jingbo Lan

  DOI：10.1039/d1cc06705b

  日期：——

  radical nucleophilic addition/rearrangement of 2-aryl diazaboroles has been accomplished for the first time to construct phenazine structures. This protocol is an umpolung strategy based on the classical electrophilic mechanism, and therefore, a reversed regioselectivity was observed, which provides an opportunity to prepare sterically hindered phenazines. The resulting thermally activated delayed fluorescence

  在此，Ag(I) 促进的 2-芳基二氮杂硼的区域选择性分子内自由基亲核加成/重排首次实现了构建吩嗪结构。该协议是一种基于经典亲电机制的 umpolung 策略，因此观察到了反向的区域选择性，这为制备空间位阻吩嗪提供了机会。由此产生的基于吩嗪的热激活延迟荧光 (TADF) 材料表现出从绿色到红色的发射带，具有高量子产率和中等荧光寿命作为固体薄膜。
• The silver-mediated annulation of arylcarbamic acids and nitrosoarenes toward phenazines
  作者：Lu Wang、Fan Chen、Peng-Cheng Qian、Jiang Cheng

  DOI：10.1016/j.tetlet.2021.153550

  日期：2022.1

  A silver-mediated annulation between arylcarbamic acids and nitrosoarenes was developed, leading to phenazines in moderate to good yields with complexity and diversity. This procedure proceeded with the sequential ortho CH functionalization of arylcarbamic acids, insertion to nitroso group and decarboxylative annulation.

  开发了芳基氨基甲酸和亚硝基芳烃之间的银介导环化，导致吩嗪产量中等至良好，具有复杂性和多样性。该过程进行了芳基氨基甲酸的连续邻位C H 官能化、插入亚硝基和脱羧环化。
• ORGANIC ELECTRONIC DEVICES, INCLUDING ORGANIC PHOTOVOLTAIC DEVICES, POLYMERS, AND MONOMERS
  申请人：GRENIER Christophe René Gaston

  公开号：US20120283377A1

  公开（公告）日：2012-11-08

  Materials for organic electronic devices including organic photovoltaic devices. An oligomer or polymer comprising: wherein R 1 , R 2 , R 3 , and R 4 are independently hydrogen or solubilizing groups. Monomers and ink compositions can be also prepared. The materials can be used in an OPV active layer and show excellent absorption properties with bathochromic shift.

  有机电子设备的材料，包括有机光伏器件。其中包括寡聚物或聚合物，其包括：其中R1、R2、R3和R4独立地为氢或增溶基团。也可以制备单体和墨水组合物。这些材料可以用于OPV活性层，并显示出优异的吸收性能和红移。
• Electro-Oxidative Synthesis of Phenazines
  作者：Deepak Sharma、Namrata Kotwal、Pankaj Chauhan

  DOI：10.1021/acs.orglett.3c01270

  日期：2023.5.26

  electro-oxidative synthesis as the general protocol for procuring phenazines under mild reaction conditions. Using aerial oxygen as an oxidant, inexpensive electrolyte, and electrodes, a diverse range of phenazines have been accessed in good yields via the ring contraction of 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepines. In addition, the syntheses of phenazines and diamino phenazines via direct electro-oxidation

  我们在此公开电氧化合成作为在温和反应条件下获得吩嗪的一般方案。使用空气中的氧气作为氧化剂、廉价的电解质和电极，通过 10,11-dihydro-5 H -dibenzo[ b,e ][1,4]diazepines的环收缩以良好的收率获得了多种吩嗪. 此外，还分别通过二氢吩嗪的直接电氧化和邻苯二胺的电二聚反应合成了吩嗪和二氨基吩嗪。