5,6,7,8-tetrahydro-10,11-dimethoxy-3-phenyl-4H-isoxazolo<4,5-f><3>benzazonine | 133910-71-1

• 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-3-phenyl-4H-isoxazolo<4,5-f><3>benzazonine
• 英文别名: 14,15-dimethoxy-5-phenyl-3-oxa-4,9-diazatricyclo[10.4.0.02,6]hexadeca-1(16),2(6),4,12,14-pentaene
• CAS: 133910-71-1
• 化学式: C₂₁H₂₂N₂O₃
• 分子量: 350.417
• InChiKey: QBEQZNWSARMWLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  56.52
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5,6,7,8-tetrahydro-10,11-dimethoxy-3-phenyl-4H-isoxazolo<4,5-f><3>benzazonine 、 溶剂黄146 反应 18.0h， 以44%的产率得到6-acetyl-5,6,7,8-tetrahydro-10,11-dimethoxy-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
• 作为产物：
  描述：

  5,6,7,8-tetrahydro-10,11-dimethoxy-3-phenyl-6-(phenylmethyl)-4H-isoxazolo<4,5-f><3>benzazonine 在 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 116.0h， 生成 5,6,7,8-tetrahydro-10,11-dimethoxy-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

• WENTLAND, MARK P.;KULLNIG, RUDOLPH K.;THAM, FOOK S., J. ORG. CHEM., 56,(1991) N5, C. 4701-4706
  作者：WENTLAND, MARK P.、KULLNIG, RUDOLPH K.、THAM, FOOK S.

  DOI：——

  日期：——