(1R,12S,20S)-12-ethyl-17-oxa-8,16-diazapentacyclo[10.7.1.01,9.02,7.016,20]icosa-2,4,6,8-tetraen-18-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉类
• 英文名称: (1R,12S,20S)-12-ethyl-17-oxa-8,16-diazapentacyclo[10.7.1.01,9.02,7.016,20]icosa-2,4,6,8-tetraen-18-ol
• 化学式: C₁₉H₂₄N₂O₂
• 分子量: 312.412
• InChiKey: WTHLFDUBDIGAAZ-JGINJTNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  45.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl (1R,12S,20S)-18-(3-chlorobenzoyl)oxy-12-ethyl-17-oxa-8,16-diazapentacyclo[10.7.1.01,9.02,7.016,20]icosa-2,4,6,9-tetraene-10-carboxylate 在 盐酸 作用下， 反应 0.17h， 以18%的产率得到(1R,12S,20S)-12-ethyl-17-oxa-8,16-diazapentacyclo[10.7.1.01,9.02,7.016,20]icosa-2,4,6,8-tetraen-18-ol
  参考文献：
  名称：

  New Rearrangement of an Aspidosperma Alkaloid. The First Biomimetic Entry in the Goniomitine Skeleton

  摘要：

  The first biomimetic approach to the skeleton of goniomitine (12) from an Aspidosperma alkaloid is described. With 16-chloro-1-dehydro-5-methoxyvincadifforme (4) (easily available from vincadifformine (1) as starting material, the rearrangement is performed in two steps: (a) Oxidation of 4 by m-CPBA followed by methanolysis affords the hemiketal 10 with a tetrahydro-1,2-oxazine structure for ring C, and (b) acid-catalyzed reaction on 10 provides either a mixture of both rearranged compounds 15 and 16 or 15 alone according to reaction time. Mechanisms of formation of 10, 15, and 16 are discussed.

  DOI：

  10.1021/jo00116a009

文献信息

• New Rearrangement of an Aspidosperma Alkaloid. The First Biomimetic Entry in the Goniomitine Skeleton
  作者：Guy Lewin、Corinne Schaeffer、Pierre Herve Lambert

  DOI：10.1021/jo00116a009

  日期：1995.6

  The first biomimetic approach to the skeleton of goniomitine (12) from an Aspidosperma alkaloid is described. With 16-chloro-1-dehydro-5-methoxyvincadifforme (4) (easily available from vincadifformine (1) as starting material, the rearrangement is performed in two steps: (a) Oxidation of 4 by m-CPBA followed by methanolysis affords the hemiketal 10 with a tetrahydro-1,2-oxazine structure for ring C, and (b) acid-catalyzed reaction on 10 provides either a mixture of both rearranged compounds 15 and 16 or 15 alone according to reaction time. Mechanisms of formation of 10, 15, and 16 are discussed.