ethyl 5-(dimethylamino)-2-[[4-[(N-ethoxycarbonyl-N-methylaminosulfonyl)methyl]phenyl]hydrazin-2-ylidene]pentanoate | 264909-33-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 5-(dimethylamino)-2-[[4-[(N-ethoxycarbonyl-N-methylaminosulfonyl)methyl]phenyl]hydrazin-2-ylidene]pentanoate
• 英文别名: ethyl 5-(dimethylamino)-2-[[4-[[ethoxycarbonyl(methyl)sulfamoyl]methyl]phenyl]hydrazinylidene]pentanoate
• CAS: 264909-33-3
• 化学式: C₂₀H₃₂N₄O₆S
• 分子量: 456.563
• InChiKey: NXYHTTOTHCGQOS-UHFFFAOYSA-N

物化性质

• 沸点：
  562.0±60.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  31.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  117.61
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-(dimethylamino)-2-[[4-[(N-ethoxycarbonyl-N-methylaminosulfonyl)methyl]phenyl]hydrazin-2-ylidene]pentanoate 在 盐酸 、 溶剂黄146 作用下， 反应 24.0h， 以80%的产率得到3-[2-(dimethylamino)ethyl]-N,2-ethoxycarbonyl-N-methyl-1H-indole-5-methanesulfonamide hydrochloride
  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：

  N-methyl-N-ethoxycarbonyl-(4-aminophenyl)methanesulfonamide hydrochloride 在 盐酸 、 sodium acetate 、 sodium nitrite 作用下， 反应 0.75h， 生成 ethyl 5-(dimethylamino)-2-[[4-[(N-ethoxycarbonyl-N-methylaminosulfonyl)methyl]phenyl]hydrazin-2-ylidene]pentanoate
  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