5,6,7,8-tetrahydro-10,11-dimethoxy-3-(4-methoxyphenyl)-6-methyl-4H-isoxazolo<4,5-f><3>benzazonine | 123420-58-6

• 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-(4-methoxyphenyl)-6-methyl-4H-isoxazolo<4,5-f><3>benzazonine
• 英文别名: 14,15-Dimethoxy-5-(4-methoxyphenyl)-9-methyl-3-oxa-4,9-diazatricyclo[10.4.0.02,6]hexadeca-1(16),2(6),4,12,14-pentaene
• CAS: 123420-58-6
• 化学式: C₂₃H₂₆N₂O₄
• 分子量: 394.47
• InChiKey: JWJSMDZXBJINEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (3RS,9bRS,12aRS)-1,4,5,12a-tetrahydro-7,8-dimethoxy-12-(4-methoxyphenyl)-3-methyl-2H-isoxazolo<5',4':2,3>pyrrolo<2,1-a>isoquinolinium iodide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 5,6,7,8-tetrahydro-10,11-dimethoxy-3-(4-methoxyphenyl)-6-methyl-4H-isoxazolo<4,5-f><3>benzazonine
  参考文献：
  名称：

  The synthesis of novel nitrogen-containing macrocycles from isoxazoline intermediates

  摘要：

  DOI：

  10.1016/s0040-4039(00)99495-4

文献信息

• Synthesis of aza-macrocycles from polycyclic 5-aminoisoxazoline precursors
  作者：Mark P. Wentland、Rudolph K. Kullnig、Fook S. Tham

  DOI：10.1021/jo00015a025

  日期：1991.7

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

  DOI：——

  日期：——
• 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：——