N,N'-diacetylhexahydropyridazine | 13645-30-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N,N'-diacetylhexahydropyridazine
• 英文别名: 1,2-diacetyl-hexahydro-pyridazine；1,2-Diacetyl-hexahydro-pyridazin；Pyridazine, 1,2-diacetylhexahydro-；1-(2-acetyldiazinan-1-yl)ethanone
• CAS: 13645-30-2
• 化学式: C₈H₁₄N₂O₂
• 分子量: 170.211
• InChiKey: AWRMAUVZOJIILN-UHFFFAOYSA-N

物化性质

• 熔点：
  59.9-62.9 °C
• 沸点：
  248.4±23.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  六氢哒嗪 、 乙酰氯 在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 N,N'-diacetylhexahydropyridazine
  参考文献：
  名称：

  Anionic [3,3] Rearrangements of Cyclic Hydrazine Diacylates to Medium-Size Cyclic Diamides and Their Structures

  摘要：

  The anionic rearrangement of N,N'-dimethyl-N,N'-diacylhydrazines to 1,2-disubstituted succinamides proceeds in the presence of a ajacent enolate-stabilizing substituent such as a phenyl group. However, a substituent that poorly stabilizes the alpha-carbanion results in an extremely-low yield of the products. The [3,3] sigmatropic rearrangement generally requires a chair form for the cyclic six-centered transition state. When the dienolates of N,N'-diacylhydrazines have favorable steric factors for the cyclic transition state, the rearrangement seems to proceed smoothly. The diacylates of 5- to 8-membered cyclic hydrazine which readily adopt a favorable conformation for the:[33] :rearrangement readily rearrange to 9- to 12-membered cyclic diamides.

  DOI：

  10.3987/com-99-8747

文献信息

• Synthesen von Bicyclen mit zwei Stickstoffatomen als Brückengliedern
  作者：M. Rink、S. Mehta、K. Grabowski

  DOI：10.1002/ardp.19592920503

  日期：——
• Anionic [3,3] Rearrangements of Cyclic Hydrazine Diacylates to Medium-Size Cyclic Diamides and Their Structures
  作者：Yasuyuki Endo、Takuya Uchida、Kentaro Yamaguchi

  DOI：10.3987/com-99-8747

  日期：——

  The anionic rearrangement of N,N'-dimethyl-N,N'-diacylhydrazines to 1,2-disubstituted succinamides proceeds in the presence of a ajacent enolate-stabilizing substituent such as a phenyl group. However, a substituent that poorly stabilizes the alpha-carbanion results in an extremely-low yield of the products. The [3,3] sigmatropic rearrangement generally requires a chair form for the cyclic six-centered transition state. When the dienolates of N,N'-diacylhydrazines have favorable steric factors for the cyclic transition state, the rearrangement seems to proceed smoothly. The diacylates of 5- to 8-membered cyclic hydrazine which readily adopt a favorable conformation for the:[33] :rearrangement readily rearrange to 9- to 12-membered cyclic diamides.