6-Bromomethyl-1,3-diphenylpyrazin-2(1H)-one | 180893-49-6

• 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: 6-Bromomethyl-1,3-diphenylpyrazin-2(1H)-one
• 英文别名: 6-bromomethyl-1,3-diphenyl-2(1H)-pyrazinone；6-(Bromomethyl)-1,3-diphenylpyrazin-2-one
• CAS: 180893-49-6
• 化学式: C₁₇H₁₃BrN₂O
• 分子量: 341.207
• InChiKey: VLVJSQNCEDDXGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 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：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Bromomethyl-1,3-diphenylpyrazin-2(1H)-one 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 生成 1,3-Diphenyl-1,5,6,7-tetrahydro-pyrrolo[3,4-b]pyridin-2-one
  参考文献：
  名称：

  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

  摘要：

  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

  DOI：

  10.1016/0040-4020(96)00467-x
• 作为产物：
  描述：

  6-Methyl-1,3-diphenylpyrazin-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80%的产率得到6-Bromomethyl-1,3-diphenylpyrazin-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

• 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
• 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。