cis-anti-cis-2,6-Dioxo-4,8-dinitrosodecahydro-1H,5H-diimidazo<4,5-b:4',5'-e>pyrazine | 133816-42-9

• 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-anti-cis-2,6-Dioxo-4,8-dinitrosodecahydro-1H,5H-diimidazo<4,5-b:4',5'-e>pyrazine
• 英文别名: cis-anti-cis-2,6-Dioxo-4,8-dinitrosodecahydro-1H,5H-diimidazo[4,5-b:4',5'-e]pyrazine
• CAS: 133816-42-9；133868-93-6
• 化学式: C₆H₈N₈O₄
• 分子量: 256.181
• InChiKey: VCLLRPMFQOUKKT-GNSDDBTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  147.6
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  cis-syn-cis-2,6-Dioxodecahydro-1H,5H-diimidazo<4,5-b:4',5'-e>pyrazine Hydrochloride 在 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 生成 cis-syn-cis-2,6-Dioxo-4,8-dinitrosodecahydro-1H,5H-diimidazo<4,5-b:4',5'-e>pyrazine 、 cis-anti-cis-2,6-Dioxo-4,8-dinitrosodecahydro-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