2,6-双(4-甲氧基苯基)吡嗪 | 135459-44-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2,6-双(4-甲氧基苯基)吡嗪
• 英文名称: 2,6-bis-(4-methoxy-phenyl)-pyrazine
• 英文别名: 2,6-bis(4-methoxyphenyl)pyrazine；2,6-Bis-(4-methoxy-phenyl)-pyrazin；Pyrazine, 2,6-bis(4-methoxyphenyl)-
• CAS: 135459-44-8
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: ORHFOUOBWRISDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-双(4-甲氧基苯基)吡嗪 在 三溴化硼 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 2,6-bis-(4-cyanomethoxy-phenyl)-pyrazine
  参考文献：
  名称：

  Synthesis of 2,6-diphenylpyrazine derivatives and their DNA binding and cytotoxic properties

  摘要：

  A series of 2,6-diphenylpyrazine derivatives was synthesized from 2,6-dichloropyrazine and 4-methoxyphenylboronic acid using palladium(0) as catalyst in a Suzuki methodology. After deprotection of the hydroxyl, alkylation reactions with different halides afforded compounds 5-8 bearing hydrophilic chains. DNA binding and cytotoxic properties were investigated. Compound 11 bearing imidazoline terminal groups was found to be a potent AT-specific DNA minor groove binder but there was no relationship between DNA interaction and cytotoxicity. However, in all cases the incorporation of the pyrazine ring was found to promote the cytotoxicity of the molecules compared to the corresponding pyridine analogues, previously synthesized. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.003
• 作为产物：
  描述：

  苯甲醚 在 二硫化碳 、 三氯化铝 、 乙醇 、 氨 作用下， 生成 2,6-双(4-甲氧基苯基)吡嗪
  参考文献：
  名称：

  Tutin, Journal of the Chemical Society, 1910, vol. 97, p. 2520

  摘要：

  DOI：

文献信息

• Diarylpyrazine-based position isomers: A detailed study of optical properties and structure-property relationship
  作者：Dong-Jin Park、Puttavva Meti、Young-Dae Gong

  DOI：10.1016/j.dyepig.2020.108254

  日期：2020.5

  A versatile and expeditious synthetic route to pyrazine-based symmetric and asymmetric chromophores decorated with donor-acceptor (D-A) has been designed to study their structural effects on optical properties. Suzuki-Miyaura coupling of dihalopyrazine with various aryl boronic acids was synthesized under microwave condition. Pyrazine functionalized at C-2, C-5 and C-6 serve as acceptor to construct

  设计了一种通用且快速的合成路线，以吡嗪为基的对称和不对称生色团装饰有供体-受体（DA），以研究其对光学性质的结构影响。在微波条件下合成了二卤代吡嗪与各种芳基硼酸的Suzuki-Miyaura偶联。在C-2，C-5和C-6上官能化的吡嗪用作受体，以构建线性和角推挽生色团。系统地研究了所有目标发色团的光物理，电化学和热性质，并通过密度泛函理论计算将结果与理论相关。通过引入强电子吸收基团（CN），发射波长显着红移。末端供体受体单元的排列以可预测的方式调节光电性能，有助于合理设计发光材料的小分子。这些生色团在不同的溶剂中表现出多色变化，表现出良好的溶剂变色性，斯托克斯位移较大。
• Selective synthesis of oxazoles and pyrazines from <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" altimg="si1.gif" overflow="scroll"><mml:mrow><mml:mi mathvariant="bold">α</mml:mi></mml:mrow></mml:math>-bromo-1-phenylethanone using a by-product-promoted strategy
  作者：Changhui Liu、Jiateng Zhao、Yu Qiao、Wenbo Huang、Zhonghao Rao、Yanlong Gu

  DOI：10.1016/j.tet.2018.10.071

  日期：2018.12

  Oxazoles and pyrazines are fundamental heterocycles that widely found in natural products or drugs. In this work, a selective strategy for oxazoles and pyrazines synthesis using α-bromo-1-phenylethanone and ammonium acetate as starting materials was reported. This methodology features mild reaction conditions, readily accessible starting materials and good chemoselectivity. Mechanistic study indicates

  恶唑和吡嗪是在天然产物或药物中广泛发现的基本杂环。在这项工作中，报道了一种以α-溴-1-苯基乙酮和乙酸铵为起始原料合成恶唑和吡嗪的选择性策略。该方法的特点是反应条件温和，原料易得，化学选择性好。机理研究表明，该反应涉及形成恶唑的副产物促进（BPP）过程，即反应过程中原位形成的溴化氢（HBr）促进了整个串联过程。