5-(2-methyl-3-indolyl)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline | 478011-82-4

• 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-(2-methyl-3-indolyl)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline
• 英文别名: 4-methoxy-6-methyl-5-(2-methyl-indol-3-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline；4-Methoxy-6-methyl-5-(2-methyl-indol-3-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isochinolin；4-methoxy-6-methyl-5-(2-methyl-1H-indol-3-yl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline
• CAS: 478011-82-4
• 化学式: C₂₁H₂₂N₂O₃
• 分子量: 350.417
• InChiKey: GNESXRZEPHWIJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 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：
  46.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-methyl-3-indolyl)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline 、 碘甲烷 以 氯仿 为溶剂， 反应 24.0h， 以90%的产率得到4-methoxy-6,6-dimethyl-5-(2-methyl-3-indolyl)-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
• 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 为溶剂， 反应 28.0h， 生成 5-(2-methyl-3-indolyl)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline
  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

文献信息

• XLIV.—Synthetical experiments in the group of the isoquinoline alkaloids. Part III. The constitution of anhydrocotarnineacetophenone, etc., together with an account of some new condensation products of cotarnine
  作者：Edward Hope、Robert Robinson

  DOI：10.1039/ct9130300361

  日期：——
• ——
  作者：K. A. Krasnov、V. G. Kartsev

  DOI：10.1023/a:1016354730304

  日期：——

  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.