1-ethyl-6-methoxy-5-nitromethyl-1,4,5,6-tetrahydropyrazine-2,3-dicarbonitrile

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-ethyl-6-methoxy-5-nitromethyl-1,4,5,6-tetrahydropyrazine-2,3-dicarbonitrile
• 英文别名: 2,3-dicyano-6-methoxy-5-nitromethyl-1,4,5,6-tetrahydropyrazine；(2R,3R)-4-ethyl-3-methoxy-2-(nitromethyl)-2,3-dihydro-1H-pyrazine-5,6-dicarbonitrile
• 化学式: C₁₀H₁₃N₅O₃
• 分子量: 251.245
• InChiKey: LRKQYRIVJOIPMG-PSASIEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-甲基喹喔啉-1-嗡 、 1-ethyl-6-methoxy-5-nitromethyl-1,4,5,6-tetrahydropyrazine-2,3-dicarbonitrile 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以51%的产率得到1-methoxy-2-ethyl-10-methyl-11-nitro-1,2,4b,5,10,10a,11,11a-octahydro-2,4a,5,10-tetraazabenzo[b]fluorene-3,4-dicarbonitrile
  参考文献：
  名称：

  Chemistry of O- and C-adducts derived from 1,4-diazinium salts: the use of tetrahydropyrazines in the synthesis of condensed systems

  摘要：

  1-Ethyl-2,3-dicyano-5-nitromethyl-6-methoxy-1,4,5,6-tetrahydropyrazine reacts with N-methylquinoxalinium iodide in the presence of triethylamine to form octahydro-2,4a,5,10-tetraazabenzo[b]fluorene-3,4-dicarbonitrile, while our attempts to obtain similar polycyclic products from stereoisomeric 5-(S)- and 5-(R)-(1'-nitroprop-1'-yl)-6-methoxy-1,4,5,6-tetrahydropyrazines derived from the reaction of 1-nitropropane with 2,3-dicyano-5,6-dimethoxy-1-ethyl-1,4,5,6-tetrahydropyrazine were unsuccessful.

  DOI：

  10.1070/mc2006v016n01abeh002153
• 作为产物：
  描述：

  2,3-二氰基吡嗪 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 264.0h， 生成 1-ethyl-6-methoxy-5-nitromethyl-1,4,5,6-tetrahydropyrazine-2,3-dicarbonitrile
  参考文献：
  名称：

  Mono- and diadducts and bicyclic adducts in reactions of 2,3-dicyano-1-ethylpyrazinium cation with C- and O-nucleophiles

  摘要：

  Products of diaddition of O- and C-nucleophiles to the 2,3-dicyano-1-ethylpyrazinium cation were isolated for the first time. The tandem AN-AN reactions of 2,3-dicyano-1-ethylpyrazinium tetrafluoroborate with 1,3-diketone enolates or keto esters afforded tetrahydrofuro[2,3-b]pyrazine derivatives, whereas cyclization with ethylene glycol gave tetrahydro1,4-dioxino[2,3-b]pyrazine. Crystallographic data on the three-dimensional structures of these compounds were reported.

  DOI：

  10.1023/b:rucb.0000042286.61289.bf

文献信息

• Chemistry of O- and C-adducts derived from 1,4-diazinium salts: the use of tetrahydropyrazines in the synthesis of condensed systems
  作者：Gennady L. Rusinov、Pavel A. Slepukhin、Valery N. Charushin、Oleg A. Dyachenko、Olga N. Kazheva、Anatolii N. Chekhlov、Egor V. Verbitsky、Michael I. Kodess、Oleg N. Chupakhin

  DOI：10.1070/mc2006v016n01abeh002153

  日期：——

  1-Ethyl-2,3-dicyano-5-nitromethyl-6-methoxy-1,4,5,6-tetrahydropyrazine reacts with N-methylquinoxalinium iodide in the presence of triethylamine to form octahydro-2,4a,5,10-tetraazabenzo[b]fluorene-3,4-dicarbonitrile, while our attempts to obtain similar polycyclic products from stereoisomeric 5-(S)- and 5-(R)-(1'-nitroprop-1'-yl)-6-methoxy-1,4,5,6-tetrahydropyrazines derived from the reaction of 1-nitropropane with 2,3-dicyano-5,6-dimethoxy-1-ethyl-1,4,5,6-tetrahydropyrazine were unsuccessful.
• Mono- and diadducts and bicyclic adducts in reactions of 2,3-dicyano-1-ethylpyrazinium cation with C- and O-nucleophiles
  作者：P. A. Slepukhin、G. L. Rusinov、V. N. Charushin、V. I. Filyakova、N. S. Karpenko、D. B. Krivolapov、I. A. Litvinov

  DOI：10.1023/b:rucb.0000042286.61289.bf

  日期：2004.6

  Products of diaddition of O- and C-nucleophiles to the 2,3-dicyano-1-ethylpyrazinium cation were isolated for the first time. The tandem AN-AN reactions of 2,3-dicyano-1-ethylpyrazinium tetrafluoroborate with 1,3-diketone enolates or keto esters afforded tetrahydrofuro[2,3-b]pyrazine derivatives, whereas cyclization with ethylene glycol gave tetrahydro1,4-dioxino[2,3-b]pyrazine. Crystallographic data on the three-dimensional structures of these compounds were reported.