6-Benzyl-10,11-dimethoxy-3-phenyl-5,6,7,8-tetrahydro-4H-1-oxa-2,6-diaza-benzo[a]cyclopenta[c]cyclononene; hydrobromide | 133910-75-5

• 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: 6-Benzyl-10,11-dimethoxy-3-phenyl-5,6,7,8-tetrahydro-4H-1-oxa-2,6-diaza-benzo[a]cyclopenta[c]cyclononene; hydrobromide
• CAS: 133910-75-5
• 化学式: BrH*C₂₈H₂₈N₂O₃
• 分子量: 521.454
• InChiKey: QXHILKCGOLKUPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.73
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  溴甲苯 、 (9bRS,12aRS)-1,4,5,12a-tetrahydro-7,8-dimethoxy-12-phenyl-2H-isoxazolo<5',4':2,3>pyrrolo<2,1-a>isoquinoline 反应 2.0h， 以77%的产率得到6-Benzyl-10,11-dimethoxy-3-phenyl-5,6,7,8-tetrahydro-4H-1-oxa-2,6-diaza-benzo[a]cyclopenta[c]cyclononene; hydrobromide
  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