6-acetyl-5,6,7,8-tetrahydro-10,11-dimethoxy-3-phenyl-4H-isoxazolo<4,5-f><3>benzazonine | 133910-72-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 英文名称: 6-acetyl-5,6,7,8-tetrahydro-10,11-dimethoxy-3-phenyl-4H-isoxazolo<4,5-f><3>benzazonine
• 英文别名: 1-(14,15-dimethoxy-5-phenyl-3-oxa-4,9-diazatricyclo[10.4.0.02,6]hexadeca-1(16),2(6),4,12,14-pentaen-9-yl)ethanone
• CAS: 133910-72-2
• 化学式: C₂₃H₂₄N₂O₄
• 分子量: 392.455
• InChiKey: GBQOWQNZNCUVTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.8
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  10,11-Dimethoxy-3-phenyl-4,5,7,8-tetrahydro-1-oxa-2,6-diaza-benzo[a]cyclopenta[c]cyclononene-6-carboxylic acid phenyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 114.0h， 生成 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

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：——