cis-syn-cis-2,6-Dioxo-1,4,7,8-tetranitrodecahydro-1H,5H-diimidazo<4,5-b:4',5'-e>pyrazine | 133816-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: cis-syn-cis-2,6-Dioxo-1,4,7,8-tetranitrodecahydro-1H,5H-diimidazo<4,5-b:4',5'-e>pyrazine
• CAS: 133816-45-2
• 化学式: C₆H₆N₁₀O₁₀
• 分子量: 378.175
• InChiKey: IKOOIKLXBDGMPN-GNSDDBTRSA-N

反应信息

• 作为反应物：
  描述：

  cis-syn-cis-2,6-Dioxo-1,4,7,8-tetranitrodecahydro-1H,5H-diimidazo<4,5-b:4',5'-e>pyrazine 、 cis-syn-cis-2,6-Dioxo-1,4,5,8-tetranitrodecahydro-1H,5H-diimidazo<4,5-b:4',5'-e>pyrazine 在 nitronium tetrafluoborate 作用下， 以 乙腈 为溶剂， 生成 cis-syn-cis-2,6-Dioxo-1,3,4,5,7,8-hexanitrodecahydro-1H,5H-diimidazo<4,5-b:4',5'-e>pyrazine
  参考文献：
  名称：

  Facile synthesis and nitration of cis-syn-cis-2,6-dioxodecahydro-1H,5H-diimidazo[4,5-b:4',5'-e]pyrazine

  摘要：

  The title ring system was synthesized for the first time by acid-promoted condensation of ureas with 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine. Nitrosation and nitration of the polycycle occurs first at the piperazine nitrogens. Successive further nitration leads to tetra-, penta-, and hexanitro derivatives. X-ray crystallographic analysis of the tetra- and hexanitro derivatives established the cis-syn-cis configuration and an all-axial conformation for this ring system. Possible reasons for the stereoselectivity of the condensation reaction are discussed.

  DOI：

  10.1021/jo00010a043
• 作为产物：
  描述：

  cis-syn-cis-2,6-Dioxodecahydro-1H,5H-diimidazo<4,5-b:4',5'-e>pyrazine Hydrochloride 在 硝酸 作用下， 以 乙酸酐 为溶剂， 反应 4.0h， 以14%的产率得到cis-syn-cis-2,6-Dioxo-1,4,5,8-tetranitrodecahydro-1H,5H-diimidazo<4,5-b:4',5'-e>pyrazine
  参考文献：
  名称：

  Facile synthesis and nitration of cis-syn-cis-2,6-dioxodecahydro-1H,5H-diimidazo[4,5-b:4',5'-e]pyrazine

  摘要：

  The title ring system was synthesized for the first time by acid-promoted condensation of ureas with 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine. Nitrosation and nitration of the polycycle occurs first at the piperazine nitrogens. Successive further nitration leads to tetra-, penta-, and hexanitro derivatives. X-ray crystallographic analysis of the tetra- and hexanitro derivatives established the cis-syn-cis configuration and an all-axial conformation for this ring system. Possible reasons for the stereoselectivity of the condensation reaction are discussed.

  DOI：

  10.1021/jo00010a043