7,9-dimethyl-7,9-diazatricyclo[4.3.1.0^1,6]decan-8-one

• 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: 7,9-dimethyl-7,9-diazatricyclo[4.3.1.0^1,6]decan-8-one
• 英文别名: (1S,6R)-7,9-dimethyl-7,9-diazatricyclo[4.3.1.01,6]decan-8-one
• 化学式: C₁₀H₁₆N₂O
• 分子量: 180.25
• InChiKey: OYGUXVFLJUXPKO-AOOOYVTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  23.55
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  甲基亚硝基脲 、 1,3-Dimethyl-4,5,6,7-tetrahydrobenzimidazol-2-one 在 potassium hydroxide 、 copper(l) chloride 作用下， 以 乙醚 、 水 为溶剂， 以47%的产率得到7,9-dimethyl-7,9-diazatricyclo[4.3.1.0^1,6]decan-8-one
  参考文献：
  名称：

  2,4-二氮杂双环[3.1.0]hexan-3-ones的合成、反应和重排

  摘要：

  Copper-mediated cyclopropanation of 1,3-dialkyl-1,3-dihydroimidazol-2-ones with diazomethane and methyl diazoacetate yields 2,4-diazabicyclo[3.1.0]hexan-3-ones and the first diaza[4.3.1]propellane. The bicyclic system survives elevated temperatures and in strongly basic and acidic solutions, but drastic conditions cleave the (C-1) (C-6) bond affording 1,3-dihydroimidazol-2-ones. Catalytic hydrogenation removes N-benzyl groups and opens the (C-1) (C-6) bond. Lithium aluminium hydride reduces 2,4-dibenzyl-2,4-diazabicyclo[3.1.0]hexan-3-one to a bicyclic aminal. Acid-induced cleavage of its imidazolidine ring is followed by unexpected transformations that probably procede via an acyclic intermediate, which comprises an azomethine ylide and an iminium moiety. 1,3-Cyclization involving both functional groups leads to N,N'-dibenzyl-trans-1,2-cyclopropanediamine, while 1,5-cyclization gives rise to the formation of N-benzylpyrrole along with N-benzylamine.

  DOI：

  10.3987/com-12-12543

文献信息

• Synthesis, Reactions, and Rearrangements of 2,4-Diazabicyclo[3.1.0]hexan-3-ones
  作者：Helmut Quast、Josef Walter Stawitz、Bodo Mueller

  DOI：10.3987/com-12-12543

  日期：——

  Copper-mediated cyclopropanation of 1,3-dialkyl-1,3-dihydroimidazol-2-ones with diazomethane and methyl diazoacetate yields 2,4-diazabicyclo[3.1.0]hexan-3-ones and the first diaza[4.3.1]propellane. The bicyclic system survives elevated temperatures and in strongly basic and acidic solutions, but drastic conditions cleave the (C-1) (C-6) bond affording 1,3-dihydroimidazol-2-ones. Catalytic hydrogenation removes N-benzyl groups and opens the (C-1) (C-6) bond. Lithium aluminium hydride reduces 2,4-dibenzyl-2,4-diazabicyclo[3.1.0]hexan-3-one to a bicyclic aminal. Acid-induced cleavage of its imidazolidine ring is followed by unexpected transformations that probably procede via an acyclic intermediate, which comprises an azomethine ylide and an iminium moiety. 1,3-Cyclization involving both functional groups leads to N,N'-dibenzyl-trans-1,2-cyclopropanediamine, while 1,5-cyclization gives rise to the formation of N-benzylpyrrole along with N-benzylamine.