5,6,7,8-tetrahydro-10,11-dimethoxy-6-methyl-3-phenyl-4H-isoxazolo<4,5-f><3>benzazonine | 123420-59-7

• 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: 5,6,7,8-tetrahydro-10,11-dimethoxy-6-methyl-3-phenyl-4H-isoxazolo<4,5-f><3>benzazonine
• 英文别名: 14,15-Dimethoxy-9-methyl-5-phenyl-3-oxa-4,9-diazatricyclo[10.4.0.02,6]hexadeca-1(16),2(6),4,12,14-pentaene
• CAS: 123420-59-7
• 化学式: C₂₂H₂₄N₂O₃
• 分子量: 364.444
• InChiKey: SIESPPIJAGXKJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  47.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (9bRS,12aRS)-1,4,5,12a-tetrahydro-7,8-dimethoxy-12-phenyl-2H-isoxazolo<5',4':2,3>pyrrolo<2,1-a>isoquinoline 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 5,6,7,8-tetrahydro-10,11-dimethoxy-6-methyl-3-phenyl-4H-isoxazolo<4,5-f><3>benzazonine
  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

文献信息

• The synthesis of novel nitrogen-containing macrocycles from isoxazoline intermediates
  作者：Mark P. Wentland

  DOI：10.1016/s0040-4039(00)99495-4

  日期：1989.1
• WENTLAND, MARK P., TETRAHEDRON LETT., 30,(1989) N2, C. 1477-1478
  作者：WENTLAND, MARK P.

  DOI：——

  日期：——