4-[2-(5-hydroxypentylidene) hydrazinyl]-N-methylbenzenemethane sulfonamide | 151140-64-6

• 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: 4-[2-(5-hydroxypentylidene) hydrazinyl]-N-methylbenzenemethane sulfonamide
• 英文别名: 1-[4-[2-(5-hydroxypentylidene)hydrazinyl]phenyl]-N-methylmethanesulfonamide
• CAS: 151140-64-6
• 化学式: C₁₃H₂₁N₃O₃S
• 分子量: 299.394
• InChiKey: QBOGTRUDEQEILB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  99.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[2-(5-hydroxypentylidene) hydrazinyl]-N-methylbenzenemethane sulfonamide 在 磷酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.5h， 生成 1-[3-(3-hydroxypropyl)-1H-indol-5-yl]-N-methylmethanesulfonamide 、 N-Methyl-C-{3-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1H-indol-5-yl}-methanesulfonamide 、 C-[3-(3-Hydroxy-propyl)-1-(tetrahydro-pyran-2-yl)-1H-indol-5-yl]-N-methyl-methanesulfonamide 、 C-[3,3'-Bis-(3-hydroxy-propyl)-1H,1'H-[2,5']biindolyl-5-yl]-N-methyl-methanesulfonamide
  参考文献：
  名称：

  An Efficient Fischer Indole Synthesis of Avitriptan, a Potent 5-HT_1D Receptor Agonist

  摘要：

  An efficient synthesis of the antimigraine drug candidate avitriptan (1, BMS 180048) is reported. The key step is a two-phase Fischer indolization reaction between hydrazine 6 and 5-chlorovaleraldehyde, 20, to give the chloropropylindole 35, which is susceptible to acid-catalyzed degradation under the reaction conditions required for its formation. Sequential coupling of 35 with piperazine, 26, and 4-chloro-5-methoxypyrimidine, 24, gives the title compound in 40-45% overall yield. Significant improvements in the syntheses of the known starting materials, hydrazine 6, 5-chlorovaleraldehyde, 20, and 4-chloro-5-methoxypyrimidine, 24, were also achieved.

  DOI：

  10.1021/jo971368q
• 作为产物：
  描述：

  4-氨基苯基-N-甲基甲烷磺酰胺 在 盐酸 、 sodium hydroxide 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 4.5h， 生成 4-[2-(5-hydroxypentylidene) hydrazinyl]-N-methylbenzenemethane sulfonamide
  参考文献：
  名称：

  An Efficient Fischer Indole Synthesis of Avitriptan, a Potent 5-HT_1D Receptor Agonist

  摘要：

  An efficient synthesis of the antimigraine drug candidate avitriptan (1, BMS 180048) is reported. The key step is a two-phase Fischer indolization reaction between hydrazine 6 and 5-chlorovaleraldehyde, 20, to give the chloropropylindole 35, which is susceptible to acid-catalyzed degradation under the reaction conditions required for its formation. Sequential coupling of 35 with piperazine, 26, and 4-chloro-5-methoxypyrimidine, 24, gives the title compound in 40-45% overall yield. Significant improvements in the syntheses of the known starting materials, hydrazine 6, 5-chlorovaleraldehyde, 20, and 4-chloro-5-methoxypyrimidine, 24, were also achieved.

  DOI：

  10.1021/jo971368q