4,4'-(pyrazine-2,6-diyl)diphenol | 171820-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4,4'-(pyrazine-2,6-diyl)diphenol
• 英文别名: 2,6-bis-(4-hydroxy-phenyl)-pyrazine；2,6-Bis-(4-hydroxy-phenyl)-pyrazin；2,6-Bis(4'-hydroxyphenyl)pyrazine；4-[6-(4-hydroxyphenyl)pyrazin-2-yl]phenol
• CAS: 171820-09-0
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: ZXEYZDSBKACRAR-UHFFFAOYSA-N

物化性质

• 熔点：
  305 °C
• 沸点：
  464.4±40.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-(pyrazine-2,6-diyl)diphenol 在 硼烷四氢呋喃络合物 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 2-[4-[6-[4-(2-Aminoethoxy)phenyl]pyrazin-2-yl]phenoxy]ethanamine
  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：

  2,6-双(4-甲氧基苯基)吡嗪 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到4,4'-(pyrazine-2,6-diyl)diphenol
  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

文献信息

• 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。
• Tutin, Journal of the Chemical Society, 1910, vol. 97, p. 2520
  作者：Tutin

  DOI：——

  日期：——
• Synthesis of 2,6-diphenylpyrazine derivatives and their DNA binding and cytotoxic properties
  作者：Nathalie Dias、Ulrich Jacquemard、Brigitte Baldeyrou、Amélie Lansiaux、Jean-François Goossens、Christian Bailly、Sylvain Routier、Jean-Yves Mérour

  DOI：10.1016/j.ejmech.2005.07.003

  日期：2005.12

  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.