(9bRS,12aRS)-12-(4-chlorophenyl)-1,4,5,12a-tetrahydro-7,8-dimethoxy-2H-isoxazolo<5',4':2,3>pyrrolo<2,1-a>isoquinoline | 133964-02-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (9bRS,12aRS)-12-(4-chlorophenyl)-1,4,5,12a-tetrahydro-7,8-dimethoxy-2H-isoxazolo<5',4':2,3>pyrrolo<2,1-a>isoquinoline
• 英文别名: (9bRS,12aRS)-12-(4-chlorophenyl)-1,4,5,12a-tetrahydro-7,8-dimethoxy-2H-isoxazolo[5',4':2,3]pyrrolo[2,1-a]isoquinoline；(1R,13R)-14-(4-chlorophenyl)-4,5-dimethoxy-16-oxa-10,15-diazatetracyclo[8.6.0.01,13.02,7]hexadeca-2,4,6,14-tetraene
• CAS: 133964-02-0
• 化学式: C₂₁H₂₁ClN₂O₃
• 分子量: 384.862
• InChiKey: QDLJQFDWTVTGLQ-IIBYNOLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.29
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (9bRS,12aRS)-12-(4-chlorophenyl)-1,4,5,12a-tetrahydro-7,8-dimethoxy-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 2.0h， 生成 3-(4-chlorophenyl)-5,6,7,8-tetrahydro-10,11-dimethoxy-6-methyl-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：

  8,9-dimethoxy-2,3,5,6-tetrahydro-1H-pyrrolo[2,1-a]isoquinolinium; bromide 、 Alpha,4-二氯苯甲醛肟 在 三乙胺 作用下， 以 氯仿 为溶剂， 以81%的产率得到(9bRS,12aRS)-12-(4-chlorophenyl)-1,4,5,12a-tetrahydro-7,8-dimethoxy-2H-isoxazolo<5',4':2,3>pyrrolo<2,1-a>isoquinoline
  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

• 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：——