1-苄基-6-溴甲基-5-氯-3-甲氧基-1H-吡嗪-2-酮 | 175468-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 1-苄基-6-溴甲基-5-氯-3-甲氧基-1H-吡嗪-2-酮
• 英文名称: 1-Benzyl-6-bromomethyl-5-chloro-3-methoxy-1H-pyrazin-2-one
• CAS: 175468-52-7
• 化学式: C₁₃H₁₂BrClN₂O₂
• 分子量: 343.607
• InChiKey: CNSRSAZWPCPWKB-UHFFFAOYSA-N

物化性质

• 沸点：
  398.9±52.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-苄基-6-溴甲基-5-氯-3-甲氧基-1H-吡嗪-2-酮 在 正丁基锂 、 sodium methylate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 1-benzyl-5-chloro-3-methoxy-6-methyl-2(1H)-pyrazinone
  参考文献：
  名称：

  Generation of 5,6-dimethylene-2(1H)-pyridinones from [3,4-b] sulfolene pyridinones and application in Diels–Alder reactions

  摘要：

  2(1H)-Pyrazinones were converted into various [3,4-b] sulfolene pyridinones 19-21, serving as precursors for thermolytic conversion into the corresponding 5,6-dimethylene 2(1 H)-pyridinone ortho-quinodimethanes. These were trapped in situ by reaction with various dienophiles. Tethering of precursor 19 with a dienophilic side chain attached to the 7-position of the [3,4-b] sulfolene pyridinone also enabled intramolecular cycloaddition when no rearrangement by 1,5-H-shift was viable. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.005
• 作为产物：
  描述：

  1-benzyl-3,5-dichloro-6-methylpyrazin-2(1H)-one 在 N-溴代丁二酰亚胺(NBS) 、 sodium methylate 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 生成 1-苄基-6-溴甲基-5-氯-3-甲氧基-1H-吡嗪-2-酮
  参考文献：
  名称：

  Sulfolene pyridinones as precursors for pyridinone ortho -quinodimethanes and their Diels–Alder adducts

  摘要：

  2(1H)-Pyrazinones were converted into [3,4-b] and [3,4-c] sulfolene pyridinones 4 and 5, serving as precursors for the corresponding 3.4- and 5.6-dimethylene 2(1H)-pyridinone ortho-quinodimethanes. These were trapped by in situ reaction with dienophiles. Tethering of 4 also enabled intramolecular cycloaddition. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02275-4

文献信息

• 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
• Sulfolene pyridinones as precursors for pyridinone ortho -quinodimethanes and their Diels–Alder adducts
  作者：Tom C Govaerts、Ilse Vogels、Frans Compernolle、Georges Hoornaert

  DOI：10.1016/s0040-4039(01)02275-4

  日期：2002.1

  2(1H)-Pyrazinones were converted into [3,4-b] and [3,4-c] sulfolene pyridinones 4 and 5, serving as precursors for the corresponding 3.4- and 5.6-dimethylene 2(1H)-pyridinone ortho-quinodimethanes. These were trapped by in situ reaction with dienophiles. Tethering of 4 also enabled intramolecular cycloaddition. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Generation of 5,6-dimethylene-2(1H)-pyridinones from [3,4-b] sulfolene pyridinones and application in Diels–Alder reactions
  作者：Tom C Govaerts、Ilse A Vogels、Frans Compernolle、Georges J Hoornaert

  DOI：10.1016/j.tet.2003.11.005

  日期：2004.1

  2(1H)-Pyrazinones were converted into various [3,4-b] sulfolene pyridinones 19-21, serving as precursors for thermolytic conversion into the corresponding 5,6-dimethylene 2(1 H)-pyridinone ortho-quinodimethanes. These were trapped in situ by reaction with various dienophiles. Tethering of precursor 19 with a dienophilic side chain attached to the 7-position of the [3,4-b] sulfolene pyridinone also enabled intramolecular cycloaddition when no rearrangement by 1,5-H-shift was viable. (C) 2003 Elsevier Ltd. All rights reserved.