2-羧基-3-[2-(二甲氨基)乙基]-N-甲基-1H-吲哚-5-甲磺酰胺 | 153654-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 2-羧基-3-[2-(二甲氨基)乙基]-N-甲基-1H-吲哚-5-甲磺酰胺
• 英文名称: 2-carboxy-3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide
• 英文别名: 3-[2-(dimethylazaniumyl)ethyl]-5-(methylsulfamoylmethyl)-1H-indole-2-carboxylate
• CAS: 153654-26-3
• 化学式: C₁₅H₂₁N₃O₄S
• 分子量: 339.415
• InChiKey: IJZXZYFPKPCDCL-UHFFFAOYSA-N

物化性质

• 沸点：
  587.0±60.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-羧基-3-[2-(二甲氨基)乙基]-N-甲基-1H-吲哚-5-甲磺酰胺 在 喹啉 、 铜 作用下， 反应 2.0h， 以80%的产率得到磺马曲坦
  参考文献：
  名称：

  5-取代吲哚衍生物的合成，第二部分。Japp-Klingemann 反应合成舒马曲坦

  摘要：

  Synthesis of selective 5-HT1B/1D receptor agonist, sumatriptan (1) was accomplished through decarboxylation of 2-carboxy-3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide (2) in quinoline with copper powder. The preparation of the acid (2) was effected through the Japp-Klingemann method thus avoiding the need for the formation of hydrazine from diazonium salt. Attempted decarboxylation in N,N-dimethylacetamide resulted in the formation of the beta-carboline (16).

  DOI：

  10.3987/com-99-8815
• 作为产物：
  描述：

  3-[2-(dimethylamino)ethyl]-2-ethoxycarbonyl-N-methyl-1H-indole-5-methanesulfonamide 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以90%的产率得到2-羧基-3-[2-(二甲氨基)乙基]-N-甲基-1H-吲哚-5-甲磺酰胺
  参考文献：
  名称：

  5-取代吲哚衍生物的合成，第二部分。Japp-Klingemann 反应合成舒马曲坦

  摘要：

  Synthesis of selective 5-HT1B/1D receptor agonist, sumatriptan (1) was accomplished through decarboxylation of 2-carboxy-3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide (2) in quinoline with copper powder. The preparation of the acid (2) was effected through the Japp-Klingemann method thus avoiding the need for the formation of hydrazine from diazonium salt. Attempted decarboxylation in N,N-dimethylacetamide resulted in the formation of the beta-carboline (16).

  DOI：

  10.3987/com-99-8815

文献信息

• Synthesis of 5-Substituted Indole Derivatives, Part II. Synthesis of Sumatriptan through the Japp-Klingemann Reaction
  作者：Béla Pete、István Bitter、Kálmán Harsányi、László Tõke

  DOI：10.3987/com-99-8815

  日期：——

  Synthesis of selective 5-HT1B/1D receptor agonist, sumatriptan (1) was accomplished through decarboxylation of 2-carboxy-3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide (2) in quinoline with copper powder. The preparation of the acid (2) was effected through the Japp-Klingemann method thus avoiding the need for the formation of hydrazine from diazonium salt. Attempted decarboxylation in N,N-dimethylacetamide resulted in the formation of the beta-carboline (16).