2,3,5,6,8,9-hexahydrodiimidazo[1,2-a:2',1'-c]pyrazine-1(10bH)-ethanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡嗪类
• 英文名称: 2,3,5,6,8,9-hexahydrodiimidazo[1,2-a:2',1'-c]pyrazine-1(10bH)-ethanol
• 英文别名: 2-(3,6,9,12-Tetrazatricyclo[7.3.0.02,6]dodec-1(12)-en-3-yl)ethanol
• 化学式: C₁₀H₁₈N₄O
• 分子量: 210.279
• InChiKey: MDNJEIIIMHGLHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  42.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三乙烯四胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 2,3,5,6,8,9-hexahydrodiimidazo[1,2-a:2',1'-c]pyrazine-1(10bH)-ethanol
  参考文献：
  名称：

  A New, Facile Synthesis of 1,4,7,10-Tetraazacyclododecane:  Cyclen

  摘要：

  This report outlines a new and efficient synthesis of cyclen (1,4,7,10-tetraazacyclododecane, 1) utilizing bis-imidazoline, 6 (1,1'-ethylenedi-2-imidazoline), with 1,2-dibromoethane. General conditions were developed, allowing for the simple, three-step synthesis of I at the multigram scale with an isolated overall yield approaching 65%. The cyclization of 6 produced by the condensation of triethylene tetraamine (TETA) with N,N-dimethylformamide dimethyl acetal, gave the twelve-membered, imidazolinium, cyclized intermediate bromide salt, 7 (2,3,4,5,6,7,8,8c-octahydro-1H-4a,6a,8a-triaza-2a-azoniacyclopent[fg]acenaphthylene), which hydrolyzed to 1 with the use of hot, aqueous caustic. Hydrolysis of 7 under milder conditions formed the 1,4,7,10-tetraazabicyclo[8.2.1]tridecan-13-one (20). Mechanistically, the formation of 7 may be rationalized as involving a diaminocarbene that undergoes an intramolecular carbon-hydrogen insertion.

  DOI：

  10.1021/jo016111d

文献信息

• A New, Facile Synthesis of 1,4,7,10-Tetraazacyclododecane:  Cyclen
  作者：Phillip S. Athey、Garry E. Kiefer

  DOI：10.1021/jo016111d

  日期：2002.6.1

  This report outlines a new and efficient synthesis of cyclen (1,4,7,10-tetraazacyclododecane, 1) utilizing bis-imidazoline, 6 (1,1'-ethylenedi-2-imidazoline), with 1,2-dibromoethane. General conditions were developed, allowing for the simple, three-step synthesis of I at the multigram scale with an isolated overall yield approaching 65%. The cyclization of 6 produced by the condensation of triethylene tetraamine (TETA) with N,N-dimethylformamide dimethyl acetal, gave the twelve-membered, imidazolinium, cyclized intermediate bromide salt, 7 (2,3,4,5,6,7,8,8c-octahydro-1H-4a,6a,8a-triaza-2a-azoniacyclopent[fg]acenaphthylene), which hydrolyzed to 1 with the use of hot, aqueous caustic. Hydrolysis of 7 under milder conditions formed the 1,4,7,10-tetraazabicyclo[8.2.1]tridecan-13-one (20). Mechanistically, the formation of 7 may be rationalized as involving a diaminocarbene that undergoes an intramolecular carbon-hydrogen insertion.