5-chloro-3-methoxy-6-methyl-1-phenyl-pyrazin-2(1H)-one | 175468-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-chloro-3-methoxy-6-methyl-1-phenyl-pyrazin-2(1H)-one
• 英文别名: 5-Chloro-3-methoxy-6-methyl-1-phenylpyrazin-2(1H)-one；5-chloro-3-methoxy-6-methyl-1-phenyl-2(1H)-pyrazinone；5-Chloro-3-methoxy-6-methyl-1-phenylpyrazin-2-one
• CAS: 175468-45-8
• 化学式: C₁₂H₁₁ClN₂O₂
• 分子量: 250.685
• InChiKey: FBLAVGYLTYMESI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  5-chloro-3-methoxy-6-methyl-1-phenyl-pyrazin-2(1H)-one 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 以96%的产率得到6-Bromomethyl-5-chloro-3-methoxy-1-phenylpyrazin-2(1H)-one
  参考文献：
  名称：

  Generation of 6-alkylidene/benzylidene-3,6-dihydropyrazin-2(1H)ones by reaction of 6-bromomethylpyrazin-2(1H)-ones with methoxide and further conversion into specific piperazine-2,5-diones and pyrazin-2(1H)-ones

  摘要：

  合成了3-芳基、3-苄基和3-甲氧基-6-(1-溴烷基/苄基)-5-氯吡嗪-2(1H)-酮6，并通过与甲氧基反应在THF中转化为新的6-烷基烯/苄基烯-5-氯-3,6-二氢吡嗪-2(1H)-酮7。在2当量的烷氧基存在下，得到了相应的5-烷氧基衍生物8。类型为6、7或8的化合物与各种亲核试剂反应生成了3,6-二氢吡嗪-2(1H)-酮、哌嗪-2,5-二酮和吡嗪-2(1H)-酮。

  DOI：

  10.1039/p19960000231
• 作为产物：
  描述：

  5-Chloro-6-methyl-1-phenylpyrazin-2(1H)-one 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 5-chloro-3-methoxy-6-methyl-1-phenyl-pyrazin-2(1H)-one
  参考文献：
  名称：

  Generation of 6-alkylidene/benzylidene-3,6-dihydropyrazin-2(1H)ones by reaction of 6-bromomethylpyrazin-2(1H)-ones with methoxide and further conversion into specific piperazine-2,5-diones and pyrazin-2(1H)-ones

  摘要：

  合成了3-芳基、3-苄基和3-甲氧基-6-(1-溴烷基/苄基)-5-氯吡嗪-2(1H)-酮6，并通过与甲氧基反应在THF中转化为新的6-烷基烯/苄基烯-5-氯-3,6-二氢吡嗪-2(1H)-酮7。在2当量的烷氧基存在下，得到了相应的5-烷氧基衍生物8。类型为6、7或8的化合物与各种亲核试剂反应生成了3,6-二氢吡嗪-2(1H)-酮、哌嗪-2,5-二酮和吡嗪-2(1H)-酮。

  DOI：

  10.1039/p19960000231

文献信息

• New routes for the synthesis of 3- and 5-substituted 2(1H)-pyrazinones
  作者：Rasha Azzam、Wim De Borggraeve、Frans Compernolle、Georges J Hoornaert

  DOI：10.1016/j.tetlet.2004.01.017

  日期：2004.2

  Furthermore, following hydrogenolysis of the 5-chloro substituent and regioselective 5-bromination, this palladium-catalysed cross-coupling approach could be extended to the synthesis of the analogous 5-substituted 2(1H)-pyrazinones.

  通过将Suzuki和Heck反应方法应用于3,5-二氯-2（1 H）-吡嗪酮制备了各种3-（杂）芳基，3-烷基和3-烯基-2（1 H）-吡嗪酮。此外，继5-氯取代基的氢解和区域选择性的5-溴化之后，这种钯催化的交叉偶联方法可以扩展到类似的5-取代的2（1 H）-吡嗪酮的合成。
• Expanding the substitution pattern of 2(1H)-pyrazinones via Suzuki and Heck reactions
  作者：Rasha Azzam、Wim M. De Borggraeve、Frans Compernolle、Georges J. Hoornaert

  DOI：10.1016/j.tet.2005.02.056

  日期：2005.4

  Various 3,5-dichloropyrazinones were substituted at the C-3 position with (hetero)aryl, alkyl and alkenyl groups by means of Suzuki and Heck reactions. The methodology could be extended to reactions on the far less reactive C-5 position by transhalogenation of the 5-Cl substituent to a 5-Br or a 5-I group prior to performing the cross-coupling. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of new pyrrolo[3,4-b]- and [3,4-c]pyridin(on)es and related 1,7-naphthyridinones and 2,7-naphthyridines via intramolecular Diels-Alder reactions of 2(1H)-pyrazinones
  作者：Kris J. Buysens、Didier M. Vandenberghe、Georges J. Hoornaert

  DOI：10.1016/0040-4020(96)00467-x

  日期：1996.7

  2(1H)-pyrazinones 7, 10 or 12 with in 6-position a 2-propynylaminomethyl or 3-butynylaminomethyl side chain undergo intramolecular Diels-Alder reactions providing cycloadducts which can he isolated or functionalised in some cases. By further thermolysis of these compounds either pyrrolo-[3,4-b]pyridinones 15/16 and/or pyrrolo[3,4-c]pyridines 17/18 or 1.7-naphthyridinones 25 and/or 2,7-naphthyridines 26 can be generated. Loss of either cyanide or isocyanate from the respective adducts is shown to be dependent on their substitution pattern. Copyright (C) 1996 Elsevier Science Ltd
• 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.
• Generation of 6-alkylidene/benzylidene-3,6-dihydropyrazin-2(1H)ones by reaction of 6-bromomethylpyrazin-2(1H)-ones with methoxide and further conversion into specific piperazine-2,5-diones and pyrazin-2(1H)-ones
  作者：Kris J. Buysens、Didier M. Vandenberghe、Suzanne M. Toppet、Georges J. Hoornaert

  DOI：10.1039/p19960000231

  日期：——

  3-Aryl-, 3-benzyl- and 3-methoxy-6-(1-bromoalkyl/benzyl)-5-chloropyrazin-2(1H)-ones 6 have been synthesised and converted into new 6-alkylidene/benzylidene-5-chloro-3,6-dihydropyrazin-2(1H)-ones 7 by reaction with methoxide in THF. With 2 equiv. of alkoxide the corresponding 5-alkoxy derivatives 8 were obtained. Reaction of compounds of type 6, 7 or 8 with various nucleophiles generated 3,6-dihydropyrazin-2(1H)-ones, piperazine-2,5-diones and pyrazin-2(1H)-ones.

  合成了3-芳基、3-苄基和3-甲氧基-6-(1-溴烷基/苄基)-5-氯吡嗪-2(1H)-酮6，并通过与甲氧基反应在THF中转化为新的6-烷基烯/苄基烯-5-氯-3,6-二氢吡嗪-2(1H)-酮7。在2当量的烷氧基存在下，得到了相应的5-烷氧基衍生物8。类型为6、7或8的化合物与各种亲核试剂反应生成了3,6-二氢吡嗪-2(1H)-酮、哌嗪-2,5-二酮和吡嗪-2(1H)-酮。