8,9-dimethoxy-2,3,5,6-tetrahydro-1H-pyrrolo[2,1-a]isoquinolinium; bromide | 123420-50-8

• 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: 8,9-dimethoxy-2,3,5,6-tetrahydro-1H-pyrrolo[2,1-a]isoquinolinium; bromide
• 英文别名: 8,9-Dimethoxy-2,3,5,6-tetrahydro-1H-pyrrolo[2,1-a]isochinolinium; Bromid；8,9-dimethoxy-2,3,5,6-tetrahydro-1H-pyrrolo[2,1-a]isoquinolin-4-ium;bromide
• CAS: 123420-50-8
• 化学式: Br*C₁₄H₁₈NO₂
• 分子量: 312.206
• InChiKey: VFZCFGOPRFFGEV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.14
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8,9-dimethoxy-2,3,5,6-tetrahydro-1H-pyrrolo[2,1-a]isoquinolinium; bromide 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 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：

  The synthesis of novel nitrogen-containing macrocycles from isoxazoline intermediates

  摘要：

  DOI：

  10.1016/s0040-4039(00)99495-4
• 作为产物：
  描述：

  3,4-二甲氧基苯乙胺 在 甲苯 、 三氯氧磷 作用下， 生成 8,9-dimethoxy-2,3,5,6-tetrahydro-1H-pyrrolo[2,1-a]isoquinolinium; bromide
  参考文献：
  名称：

  Synthesis of Dimethylapoerysopine and an Approach to the Total Synthesis of the Unrearranged Erythrina Bases

  摘要：

  DOI：

  10.1021/ja01608a040

文献信息

• The synthesis of novel nitrogen-containing macrocycles from isoxazoline intermediates
  作者：Mark P. Wentland

  DOI：10.1016/s0040-4039(00)99495-4

  日期：1989.1
• 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：——
• Synthesis of Dimethylapoerysopine and an Approach to the Total Synthesis of the Unrearranged Erythrina Bases
  作者：K. Wiesner、Z. Valenta、A. J. Manson、F. W. Stonner

  DOI：10.1021/ja01608a040

  日期：1955.2.1
• 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.