(9S,9aS)-N,N-dimethyl-2-(2,3,5,6,9,9a-hexahydro-1H-pyrrolo[1,2-a]azepin-3-on-9-yl)acetamide | 1298024-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - Pyrroloazepines
• 英文名称: (9S,9aS)-N,N-dimethyl-2-(2,3,5,6,9,9a-hexahydro-1H-pyrrolo[1,2-a]azepin-3-on-9-yl)acetamide
• 英文别名: 2-[(9S,9aS)-3-oxo-1,2,5,6,9,9a-hexahydropyrrolo[1,2-a]azepin-9-yl]-N,N-dimethylacetamide
• CAS: 1298024-01-7
• 化学式: C₁₃H₂₀N₂O₂
• 分子量: 236.314
• InChiKey: JHLLDIRQQPLFSC-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  1,1-二甲氧基-N,N-二甲基乙胺 、 (7S)-7-hydroxy-1,2,5,6,7,9a-hexahydropyrrolo[1,2-a]azepin-3-one 以 二乙二醇二甲醚 为溶剂， 反应 0.25h， 生成 (9S,9aR)-N,N-dimethyl-2-(2,3,5,6,9,9a-hexahydro-1H-pyrrolo[1,2-a]azepin-3-on-9-yl)acetamide 、 (9S,9aS)-N,N-dimethyl-2-(2,3,5,6,9,9a-hexahydro-1H-pyrrolo[1,2-a]azepin-3-on-9-yl)acetamide
  参考文献：
  名称：

  Total Synthesis of (–)-Sessilifoliamide C and (–)-8-epi-Stemoamide

  摘要：

  A convergent route featuring [3,3]-sigmatropic rearrangements of a linchpin azepinopyrrolidine served to install two of the four contiguous stereocenters present in the tricyclic Stemona alkaloids sessilifollamide and stemoamide. In addition to the first total synthesis of (-)-sessilifoliamide C, a potential biosynthetic relationship between the sessilifoliamides and previously reported Stemona alkaloids is presented.

  DOI：

  10.1021/ol200743u

文献信息

• Total Synthesis of (–)-Sessilifoliamide C and (–)-8-<i>epi</i>-Stemoamide
  作者：Adam T. Hoye、Peter Wipf

  DOI：10.1021/ol200743u

  日期：2011.5.20

  A convergent route featuring [3,3]-sigmatropic rearrangements of a linchpin azepinopyrrolidine served to install two of the four contiguous stereocenters present in the tricyclic Stemona alkaloids sessilifollamide and stemoamide. In addition to the first total synthesis of (-)-sessilifoliamide C, a potential biosynthetic relationship between the sessilifoliamides and previously reported Stemona alkaloids is presented.