(3S,4R)-3,4-Diphenyl-1,6-diaza-cycloundecane-2,5-dione | 137250-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3S,4R)-3,4-Diphenyl-1,6-diaza-cycloundecane-2,5-dione
• 英文别名: (3S,4R)-3,4-diphenyl-1,6-diazacycloundecane-2,5-dione
• CAS: 137250-77-2
• 化学式: C₂₁H₂₄N₂O₂
• 分子量: 336.434
• InChiKey: ZMVDKIFZXMBTGZ-KDURUIRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  perhydrodiazepine 在 正丁基锂 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 6.0h， 生成 (3S,4R)-3,4-Diphenyl-1,6-diaza-cycloundecane-2,5-dione
  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

• Anionic 3,4-diaza[3,3]sigmatropic rearrangements of N,N′-diacylhydrazines
  作者：Yasuyuki Endo、Koichi Shudo

  DOI：10.1016/0040-4039(91)80028-5

  日期：1991.1

  N,N′-Diacylhydrazines rearrange under basic conditions to afford 1,2-disubstituted succinamides. The rearrangement can be rationalized in terms of [3,3]sigmatropic shifts of biscarboxamide enolates.

  N，N′-二酰基肼在碱性条件下重排，得到1，2-二取代的琥珀酰胺。重排可以根据双羧甲酰胺烯酸酯的[3，3]σ位移而合理化。