(10bRS,13aRS)-1,2,3,5,6,13a-hexahydro-8,9-dimethoxy-13-phenylisoxazolo<6',5':3,4>pyrido<2,1-a>isoquinoline | 133910-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (10bRS,13aRS)-1,2,3,5,6,13a-hexahydro-8,9-dimethoxy-13-phenylisoxazolo<6',5':3,4>pyrido<2,1-a>isoquinoline
• CAS: 133910-69-7
• 化学式: C₂₂H₂₄N₂O₃
• 分子量: 364.444
• InChiKey: SXJUUDIWHFMEIJ-JTSKRJEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  43.29
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (10bRS,13aRS)-1,2,3,5,6,13a-hexahydro-8,9-dimethoxy-13-phenylisoxazolo<6',5':3,4>pyrido<2,1-a>isoquinoline 、 碘甲烷 反应 96.0h， 以9%的产率得到4,5,6,7,8,9-hexahydro-11,12-dimethoxy-3-phenyl-7,7-dimethyl-4H-isoxazolo<4,5-g><3>benzazecinium iodide
  参考文献：
  名称：

  Synthesis of aza-macrocycles from polycyclic 5-aminoisoxazoline precursors

  摘要：

  A series of novel isoxazolo analogues 11 of the dibenzazonine alkaloid protostephanine (1) has been prepared. A new regiospecific and potentially general aza macrocyclic ring forming process was developed where the first step was the 1,3-dipolar cycloaddition of benzonitrile oxide to the readily available enamine 6. The product, isoxazoline 9a, under solvolytic conditions that normally convert monocyclic 5-aminoisoxazolines to isoxazoles failed to give the desired aza macrocycle 14. Alternate sequences involving quaternization of 9a with methyl iodide followed by either solvolysis in polar solvents or base-induced elimination were successful and gave the target structure 11a in excellent overall yield. X-ray crystallographic analysis of the quaternized intermediate 10a corroborated the assignment of structure and defined the crystal-state conformation.

  DOI：

  10.1021/jo00015a025
• 作为产物：
  描述：

  9,10-dimethoxy-1,2,3,4,6,7-hexahydrobenzoquinolizinium chloride 、 ALPHA-氯-4-甲氧基苯甲醛肟 在 三乙胺 作用下， 以 氯仿 为溶剂， 以82%的产率得到(10bRS,13aRS)-1,2,3,5,6,13a-hexahydro-8,9-dimethoxy-13-phenylisoxazolo<6',5':3,4>pyrido<2,1-a>isoquinoline
  参考文献：
  名称：

  Synthesis of aza-macrocycles from polycyclic 5-aminoisoxazoline precursors

  摘要：

  A series of novel isoxazolo analogues 11 of the dibenzazonine alkaloid protostephanine (1) has been prepared. A new regiospecific and potentially general aza macrocyclic ring forming process was developed where the first step was the 1,3-dipolar cycloaddition of benzonitrile oxide to the readily available enamine 6. The product, isoxazoline 9a, under solvolytic conditions that normally convert monocyclic 5-aminoisoxazolines to isoxazoles failed to give the desired aza macrocycle 14. Alternate sequences involving quaternization of 9a with methyl iodide followed by either solvolysis in polar solvents or base-induced elimination were successful and gave the target structure 11a in excellent overall yield. X-ray crystallographic analysis of the quaternized intermediate 10a corroborated the assignment of structure and defined the crystal-state conformation.

  DOI：

  10.1021/jo00015a025