3,5-dichloro-6-(2-methoxy-phenyl)-1-phenylpyrazin-2(1H)-one | 723743-78-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-dichloro-6-(2-methoxy-phenyl)-1-phenylpyrazin-2(1H)-one
• 英文别名: 3,5-Dichloro-6-(2-methoxyphenyl)-1-phenylpyrazin-2-one
• CAS: 723743-78-0
• 化学式: C₁₇H₁₂Cl₂N₂O₂
• 分子量: 347.2
• InChiKey: KRHRKTSXZCAWAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-dichloro-6-(2-methoxy-phenyl)-1-phenylpyrazin-2(1H)-one 在 碘 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 5-chloro-6-(2-methoxyphenyl)-8-oxo-7-phenyl-7,8-dihydroimidazo-[1,2-a]pyrazine-3-carbaldehyde
  参考文献：
  名称：

  不同取代的咪唑并[1,2-a]pyrazine-8-oxo-3-carbaldehydes：碘介导的环化/氧化方法

  摘要：

  已经开发了一种温和有效的碘介导的分子内杂环化方法，用于构建咪唑并 [1,2-a] 吡嗪酮核。在环境条件下，这种不含金属的方案可以通过环化和后续从含有末端炔烃的底物轻松获得密集功能化的咪唑并[1,2-a]吡嗪酮-3-甲醛或（氨甲基）咪唑并[1,2-a]吡嗪酮氧化或胺化。通过在环化生成多取代的（二氢）咪唑并[1,2-a]吡嗪酮之后使用含有内部炔烃和/或Suzuki偶联的底物，可以引入进一步的多样化。

  DOI：

  10.1002/ejoc.201201150
• 作为产物：
  描述：

  草酰氯 、 在 三乙胺盐酸盐 、 N,N-二甲基甲酰胺 作用下， 以 甲苯 为溶剂， 反应 48.75h， 生成 3,5-dichloro-6-(2-methoxy-phenyl)-1-phenylpyrazin-2(1H)-one
  参考文献：
  名称：

  Synthesis and fungicidal activity of 3,5-dichloropyrazin-2(1H)-one derivatives

  摘要：

  We synthesized a family of 3,5-dichloropyrazin-2(1H)-one derivatives and assessed their in vitro fungicidal activity against Candida albicans. Compounds 11 and 20 were most active against C. albicans and induced accumulation of reactive oxygen species in this pathogen. Using a genome-wide approach in the yeast Saccharomyces cerevisiae, we demonstrated that genes involved in vacuolar functionality and DNA-related functions play an important role in cellular mechanisms underlying the fungicidal activity of these compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.024

文献信息

• Alkylation of 3,5-dichloro-2(1H)-pyrazinones using malonate esters
  作者：Nigam M. Mishra、Vsevolod A. Peshkov、Olga P. Pereshivko、Sachin G. Modha、Erik V. Van der Eycken

  DOI：10.1016/j.tetlet.2012.06.080

  日期：2012.8

  3-alkylation of 3,5-dichloro-2(1H)-pyrazinones with various malonate esters is described. The method constitutes a simple example of a C–C bond forming process at the 3-position of the pyrazinone core allowing to attain 3-substituted pyrazinones in good to high yields. 3-Alkylation of 3,5-dichloro-2(1H)-pyrazinones with acetoacetic ester was accompanied by further retro-Claisen fragmentation.

  描述了有效的碱促进的3，5-二氯-2（1 H）-吡嗪酮与各种丙二酸酯的3-烷基化。该方法构成了吡嗪酮核心3位上C–C键形成过程的简单示例，可实现以高产率或高产率获得3-取代的吡嗪酮。3，5-二氯-2（1 H）-吡嗪酮与乙酰乙酸酯的3-烷基化反应伴随着进一步的克莱森反裂解。
• <i>N</i>-Heterocyclic Carbene Catalyzed Aroylation of 3,5-Dichloro-2(1<i>H</i>)-pyrazinones
  作者：Vaibhav P. Mehta、Ajendra kumar Sharma、Sachin G. Modha、Sweta Sharma、Thirumal Meganathan、Virinder Singh Parmar、Erik Van der Eycken

  DOI：10.1021/jo200155n

  日期：2011.4.15

  The N-heterocyclic carbene catalyzed chemoselective C3-aroylation of 3,5-dichloro-2(1H)-pyrazinones with various aldehydes is reported. We herein describe results of this remarkable mild and efficient procedure.
• Diversely Substituted Imidazo[1,2-<i>a</i>]pyrazine-8-oxo-3-carbaldehydes: An Iodine-Mediated Cyclization/Oxidation Approach
  作者：Nigam M. Mishra、Dipak D. Vachhani、Sachin G. Modha、Erik V. Van der Eycken

  DOI：10.1002/ejoc.201201150

  日期：2013.2

  and efficient iodine-mediated intramolecular heteroannulation approach for the construction of the imidazo[1,2-a]pyrazinone core has been developed. Under ambient conditions, this metal-free protocol allows easy access to densely functionalized imidazo[1,2-a]pyrazinone-3-carbaldehydes or (aminomethyl)imidazo[1,2-a]pyrazinones from substrates containing terminal alkynes by cyclization and subsequent

  已经开发了一种温和有效的碘介导的分子内杂环化方法，用于构建咪唑并 [1,2-a] 吡嗪酮核。在环境条件下，这种不含金属的方案可以通过环化和后续从含有末端炔烃的底物轻松获得密集功能化的咪唑并[1,2-a]吡嗪酮-3-甲醛或（氨甲基）咪唑并[1,2-a]吡嗪酮氧化或胺化。通过在环化生成多取代的（二氢）咪唑并[1,2-a]吡嗪酮之后使用含有内部炔烃和/或Suzuki偶联的底物，可以引入进一步的多样化。
• Synthesis and fungicidal activity of 3,5-dichloropyrazin-2(1H)-one derivatives
  作者：Isabelle E.J.A. François、Bruno P.A. Cammue、Sara Bresseleers、Hein Fleuren、Georges Hoornaert、Vaibhav P. Mehta、Sachin G. Modha、Erik V. Van der Eycken、Karin Thevissen

  DOI：10.1016/j.bmcl.2009.06.024

  日期：2009.8

  We synthesized a family of 3,5-dichloropyrazin-2(1H)-one derivatives and assessed their in vitro fungicidal activity against Candida albicans. Compounds 11 and 20 were most active against C. albicans and induced accumulation of reactive oxygen species in this pathogen. Using a genome-wide approach in the yeast Saccharomyces cerevisiae, we demonstrated that genes involved in vacuolar functionality and DNA-related functions play an important role in cellular mechanisms underlying the fungicidal activity of these compounds. (C) 2009 Elsevier Ltd. All rights reserved.