2,5-二氯-3,6-二甲基吡嗪 | 27023-19-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2,5-二氯-3,6-二甲基吡嗪
• 英文名称: 2,5-dichloro-3,6-dimethylpyrazine
• 英文别名: 2,5-dichloro-3,6-dimethylpyrazine 4-oxide；2,5-dichloro-3,6-dimethyl-pyrazine；2,5-Dichlor-3,6-dimethyl-pyrazin；2,5-Dichloro-3,6-dimethylpyrazin；2,5-Dichlor-3,6-dimethylpyrazin
• CAS: 27023-19-4
• 化学式: C₆H₆Cl₂N₂
• mdl: MFCD08236788
• 分子量: 177.033
• InChiKey: NKIZSFXAIKPBCL-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73℃
• 沸点：
  217℃
• 密度：
  1.337
• 闪点：
  105℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2,5-二氯-3,6-二甲基吡嗪 在 1,4-二氧六环 、 氢氧化钾 作用下， 生成 3,6-二甲基-1H-吡嗪-2-酮
  参考文献：
  名称：

  221.吡嗪衍生物。第三部分 将二酮哌嗪转化为吡嗪衍生物。6-二- ：2-羟基3的合成秒从。-butylpyrazine异亮氨酸

  摘要：

  DOI：

  10.1039/jr9470001179
• 作为产物：
  描述：

  3,6-二甲基-1H-吡嗪-2-酮 在 吡啶 、 溴 、 溶剂黄146 、 三氯氧磷 作用下， 生成 2,5-二氯-3,6-二甲基吡嗪
  参考文献：
  名称：

  Displacements and Nuclear Substitutions on Hydroxypyrazines

  摘要：

  DOI：

  10.1021/ja01597a057

文献信息

• Studies on pyrazines. Part 32. Synthesis of trisubstituted and tetrasubstituted pyrazines as ant pheromones
  作者：Nobuhiro Sato、Tomoyuki Matsuura

  DOI：10.1039/p19960002345

  日期：——

  The synthesis of trialkylpyrazines having methyl groups on C-2 and C-5 is described, which is completed by the cross-coupling reaction of 2-chloro-3,6-dimethylpyrazine with dialkylzinc in the presence of [1,3-bis(diphenylphosphino)propane] nickel(II) chloride. Similarly, 2,5-diisobutyl-, -diisopropyl- and -di-sec-butyl-3-methylpyrazines are prepared from the corresponding dialkyl chloropyrazines. The dimethyl products are acylated with an α-keto acid under the Minisci radical conditions providing 2-acyl-5-alkyl-3,6-dimethylpyrazines. Several compounds obtained in this study prove to be active as components of pheromones in ants.

  本文描述了具有C-2和C-5位甲基的三烷基吡嗪的合成方法，该合成通过2-氯-3,6-二甲基吡嗪与二烷基锌在[1,3-双(二苯基膦基)丙烷]镍(II)氯化物的催化下进行交叉耦合反应完成。类似地，从相应的二烷基氯吡嗪制备了2,5-二异丁基-、二异丙基-和二仲丁基-3-甲基吡嗪。二甲基产物通过Minisci自由基条件下与α-酮酸的酰化反应，得到了2-酰基-5-烷基-3,6-二甲基吡嗪。本研究中得到的几种化合物证实作为蚂蚁信息素的组成部分具有活性。
• Large-Scale Solvent-Free Chlorination of Hydroxy-Pyrimidines, -Pyridines, -Pyrazines and -Amides Using Equimolar POCl3
  作者：Han Wang、Kun Wen、Le Wang、Ye Xiang、Xiaocheng Xu、Yongjia Shen、Zhihua Sun

  DOI：10.3390/molecules17044533

  日期：——

  Chlorination with equimolar POCl3 can be efficiently achieved not only for hydroxypyrimidines, but also for many other substrates such as 2-hydroxy-pyridines, -quinoxalines, or even -amides. The procedure is solvent-free and involves heating in a sealed reactor at high temperatures using one equivalent of pyridine as base. It is suitable for large scale (multigram) batch preparations.

  使用等摩尔量的POCl3对羟基嘧啶进行氯化不仅是有效的，而且对许多其他底物，如2-羟基吡啶、喹唑啉或甚至酰胺也是如此。该过程是无溶剂的，涉及在密封反应器中高温加热，使用一当量的吡啶作为碱。它适用于大规模（多克级）批次制备。
• 2,5-Di(aryleneethynyl)pyrazine derivatives: synthesis, structural and optoelectronic properties, and light-emitting device
  作者：Liang Zhao、Igor F. Perepichka、Figen Türksoy、Andrei S. Batsanov、Andrew Beeby、Karen S. Findlay、Martin R. Bryce

  DOI：10.1039/b401867m

  日期：——

  A series of 2,5-di(aryleneethynyl)pyrazine derivatives has been synthesised in 23–41% yields by two-fold reaction of 2,5-dibromo-3,6-dimethylpyrazine 3 with ethynylarenes (arene = phenyl, 2-pyridyl, 4-ethylphenyl, 4-chlorophenyl, 4-biphenyl) under standard Sonogashira conditions [CuI, Pd(PPh3)2Cl2, NEt3, THF]. Compound 3 has been converted into 2,5-diethynyl-3,6-dimethylpyrazine, which reacts with 2-iodothiophene to yield 2,5-bis(thien-2-ylethynyl)-3,6-dimethylpyrazine. In the X-ray crystal structure of 2,5-di(phenylethynyl)-3,6-dimethylpyrazine 4 the two phenyl rings are parallel and the pyrazine ring is inclined to their planes by 14.2°. Quantum chemical calculations establish that the HOMO–LUMO gap for 4 (3.56 eV) is lower than that of di(phenylethynyl)benzene 12 (3.72 eV). The nitrogen atoms of 4 serve to localise the HOMO on the central ring’s carbon atoms, resulting in a quinoidal-type population, in contrast to 12. Cyclic voltammetric studies establish that 4 undergoes a reduction to the radical anion at ca. −1.9 V (vs. Ag/Ag+ in MeCN), which is almost reversible at high scan rates (500 mV s−1). The UV-vis absorption and photoluminescence profiles of 4 in cyclohexane are similar to those of 12; the emission for 4 (λmax 379 and 395 nm) is red-shifted compared to 12. Single-layer OLEDs using MEH-PPV as the emissive polymer show significantly enhanced external quantum efficiencies (up to 0.07%) when 20% by weight of 2,5-di(biphenyl-4-ethynyl)-3,6-dimethylpyrazine 8 is added as a dopant: this is ascribed to the enhanced electron-transporting properties of the pyrazine system.

  通过2,5-二溴-3,6-二甲基吡嗪3与乙炔基芳烃(芳烃=苯基、2-吡啶基、4-乙基苯基、4-氯苯基、4-联苯基)在标准Sonogashira条件下[CuI, Pd(PPh3)2Cl2, NEt3, THF]进行二重反应,合成了一系列2,5-二(芳撑乙炔基)吡嗪衍生物,产率为23%-41%。化合物3已转化为2,5-二乙炔基-3,6-二甲基吡嗪,它与2-碘噻吩反应生成2,5-二(苯并噻吩-2-乙炔基)-3,6-二甲基吡嗪。在2,5-二(苯乙炔基)-3,6-二甲基吡嗪4的X射线晶体结构中,两个苯基环平行,吡嗪环与它们的平面倾斜14.2°。量子化学计算表明,4的最高占据分子轨道-最低未占分子轨道能隙(3.56 eV)低于二(苯乙炔基)苯12的(3.72 eV)。与12相反,4的氮原子使最高占据分子轨道局域在中心环的碳原子上,导致类醌型分布。循环伏安研究表明,4在大约-1.9 V(相对于MeCN中的Ag/Ag+)处被还原为自由基阴离子,在高扫描速率(500 mV s-1)下几乎可逆。4在环己烷中的紫外-可见吸收和光致发光光谱与12相似;4的发射峰(λmax 379和395 nm)比12的红移。使用MEH-PPV作为发光聚合物时,当2,5-二(联苯-4-乙炔基)-3,6-二甲基吡嗪8以20%的重量作为掺杂剂添加时,单层有机发光二极管的外部量子效率显著提高(高达0.07%):这归因于吡嗪系统的增强电子传输特性。
• Studies on Pyrazines; 21.¹A Convenient Synthesis of Pyrazinecarboxylic Acid Derivatives from Chloropyrazines
  作者：Ryo Takeuchi、Katsunobu Suzuki、Nobuhiro Sato

  DOI：10.1055/s-1990-27055

  日期：——

  Palladium-catalyzed carbonylation of chloropyrazines in methanol led to pyrazinecarboxylic esters in good yields. Similarly, pyrazinecarboxamides were obtained by using dialkylamines or alkylamines as the solvent.

  在甲醇中，以钯催化的氯吡嗪羰基化反应生成了产量良好的吡嗪羧酸酯。同样，使用二烷基胺或烷基胺作为溶剂也成功获得了吡嗪羧酸胺。
• Modular Synthesis of Polybenzo[<i>b</i>]silole Compounds for Hole-Blocking Material in Phosphorescent Organic Light Emitting Diodes
  作者：Laurean Ilies、Yoshiharu Sato、Chikahiko Mitsui、Hayato Tsuji、Eiichi Nakamura

  DOI：10.1002/asia.201000112

  日期：——

  utilized as efficient hole‐blocking materials for phosphorescent organic light emitting diodes (OLEDs). Some of these compounds showed a performance surpassing that of the current standard, bathocuproine. The new compounds were easily synthesized in a modular fashion from a previously reported 3‐stannyl benzosilole building unit. Studies on the properties of these compounds in solution and in the solid state

  面向多样性的合成策略使我们能够设计一系列包含多个苯并甲硅烷基单元的共轭分子，这些共轭分子可用作磷光有机发光二极管（OLED）的有效空穴阻挡材料。这些化合物中的一些表现出超过当前标准浴铜嘌呤的性能。新化合物很容易以模块化方式由先前报道的3-锡烷基苯并甲硅烷基建筑单元合成。对这些化合物在溶液和固态下的性质的研究表明，它们具有高电子亲和力，高电离势能，并形成显示出高电子漂移迁移率的稳定非晶膜。还研究了它们的分子性质与OLED器件性能效率之间的相关性。