3,5-Dichloro-1-paramethoxyphenyl-2(1H)-pyrazinone | 130879-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-Dichloro-1-paramethoxyphenyl-2(1H)-pyrazinone
• 英文别名: 3,5-dichloropyrazin-2(1H)-one；3,5-dichloro-2-(4-methoxy-phenyl)pyrazin-2-(1H)-one；3,5-Dichloro-1-(4-methoxyphenyl)pyrazin-2-one
• CAS: 130879-25-3
• 化学式: C₁₁H₈Cl₂N₂O₂
• 分子量: 271.103
• InChiKey: YSEQCFKPNCSVRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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-1-paramethoxyphenyl-2(1H)-pyrazinone 在 三苯基膦氯金 、 silver trifluoromethanesulfonate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 5-chloro-7-(4-methoxyphenyl)-3-methylimidazo[1,2-a]pyrazin-8(7H)-one
  参考文献：
  名称：

  通过金催化的炔丙基氨基吡嗪酮的区域选择性杂环化，轻松实现面向多样性的咪唑并[1,2- a ]吡嗪酮的合成

  摘要：

  已经开发了一种金催化的区域选择性异环化策略，用于简洁有效地合成咪唑并[1,2- a ]吡嗪酮。该协议允许通过应用取代的炔丙基胺或通过将生成的咪唑并[1,2- a ]吡嗪酮与各种（杂）芳基硼酸进行铃木偶联来引入多样性。

  DOI：

  10.1016/j.tet.2012.10.019
• 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 48.0h， 生成 3,5-Dichloro-1-paramethoxyphenyl-2(1H)-pyrazinone
  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。
• 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。
• Generation of specifically substituted pyridines and pyridones from 2(1h) pyrazinones and acetylenes : A FMO description
  作者：M. Tutonda、D. Vanderzande、M. Hendrickx、G. Hoornaert

  DOI：10.1016/s0040-4020(01)87770-x

  日期：1990.1

  The title compounds were obtained from reaction of variously substituted 2(1H)pyrazinones with acetylenic derivatives. Experimental evidence points out to a two step mechanism : a Diels Alder cycloaddition followed by immediate decomposition of the adducts into the title products via two competitive retro Diels Alder reactions. The product distribution, which is shown to be highly dependent on the

  标题化合物获自各种取代的2（1H）吡嗪酮与炔属衍生物的反应。实验证据指出了两步机理：Diels Alder环加成反应，然后通过两个竞争性Diels Alder逆向反应将加合物立即分解为标题产物。一个简单的FMO模型可以说明产物分布高度依赖于反应物的取代模式。
• Microwave-Assisted Synthesis of Pyrazino[2,1-b]quinazolines and 3-Indolyl-2(1H)-pyrazinones Employing a Chemoselective Silver(I)- and Gold(I)-Catalyzed Reaction
  作者：Dipak D. Vachhani、Vaibhav P. Mehta、Sachin G. Modha、Kristof Van Hecke、Luc VanMeervelt、Erik V. Van der Eycken

  DOI：10.1002/adsc.201100881

  日期：2012.5.21

  Novel microwave‐assisted syntheses of pyrazino[2,1‐b]quinazolines and 3‐indolyl‐2(1H)‐pyrazinones employing silver(I)‐ or gold(I)‐catalyzed protocols have been elaborated. The scope and limitations of these processes have been investigated.

  吡嗪并[2,1-的新颖微波辅助合成b ]喹唑啉和3-吲哚基- 2（1 ħ）-pyrazinones采用银（I） -或金（I） -催化的协议已被详细阐述。已经研究了这些方法的范围和局限性。
• 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.