5-(5-bromo-1-indolyl)-4-methoxy-6,6-dimethyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolinium iodide

• 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-(5-bromo-1-indolyl)-4-methoxy-6,6-dimethyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolinium iodide
• 英文别名: 5-(5-bromoindol-1-yl)-4-methoxy-6,6-dimethyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-ium;iodide
• 化学式: C₂₁H₂₂BrN₂O₃*I
• 分子量: 557.226
• InChiKey: WEFADBCPHLZCJZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-二氧杂环戊烯并[4,5-g]异喹啉-5-醇,5,6,7,8-四氢-4-甲氧基-6-甲基- 以 甲醇 、 氯仿 为溶剂， 反应 24.0h， 生成 5-(5-bromo-1-indolyl)-4-methoxy-6,6-dimethyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolinium iodide
  参考文献：
  名称：

  吲哚及其衍生物与可乐宁的反应。5-（1-吲哚基）-4-甲氧基-6-甲基-5,6,7,8-四氢[1,3]二氧杂环[4,5-g]异喹啉的重排

  摘要：

  A synthetic route to compounds of the indolyltetrahydroisoquinoline series was developed on the basis of the reaction of cotarnine with indole derivatives. Aminoalkylation of indole and its derivatives with cotarnine occurs regioselectively at the nitrogen atom of the indole fragment to give the corresponding 5-(1-indolyl)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolines. The products were found to undergo rearrangement into isomeric 5-(3-indolyl)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolines which constitute a new class of indolyltetrahydroisoquinoline systems.

  DOI：

  10.1023/a:1016354730304