(7S,9aS)-7-butyryloxy-2,3,5,6,7,9a-hexahydro-1H-pyrrolo[1,2-a]azepin-3-one | 1298024-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - Pyrroloazepines
• 英文名称: (7S,9aS)-7-butyryloxy-2,3,5,6,7,9a-hexahydro-1H-pyrrolo[1,2-a]azepin-3-one
• 英文别名: [(7S,9aS)-3-oxo-1,2,5,6,7,9a-hexahydropyrrolo[1,2-a]azepin-7-yl] butanoate
• CAS: 1298024-06-2
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: KKQBKRXYVUHNQI-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (7S)-7-hydroxy-1,2,5,6,7,9a-hexahydropyrrolo[1,2-a]azepin-3-one 、 丁酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 (7S,9aS)-7-butyryloxy-2,3,5,6,7,9a-hexahydro-1H-pyrrolo[1,2-a]azepin-3-one 、 (7S,9aR)-7-butyryloxy-2,3,5,6,7,9a-hexahydro-1H-pyrrolo[1,2-a]azepin-3-one
  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.