4,5,6,7,8,9-hexahydro-11,12-dimethoxy-3-phenyl-7-(1-propyl)-4H-isoxazolo<4,5-g><3>benzazecine | 133910-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,5,6,7,8,9-hexahydro-11,12-dimethoxy-3-phenyl-7-(1-propyl)-4H-isoxazolo<4,5-g><3>benzazecine
• 英文别名: 15,16-Dimethoxy-5-phenyl-10-propyl-3-oxa-4,10-diazatricyclo[11.4.0.02,6]heptadeca-1(17),2(6),4,13,15-pentaene
• CAS: 133910-74-4
• 化学式: C₂₅H₃₀N₂O₃
• 分子量: 406.525
• InChiKey: ADKZYADRBFSKJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  9,10-dimethoxy-1,2,3,4,6,7-hexahydrobenzoquinolizinium chloride 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 40.0h， 生成 4,5,6,7,8,9-hexahydro-11,12-dimethoxy-3-phenyl-7-(1-propyl)-4H-isoxazolo<4,5-g><3>benzazecine
  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：——