N-{4-[2-(benzylmethylsulfamoyl)ethyl]phenyl}-N-(2,2-dimethoxyethyl)-2,2,2-trifluoroacetamide | 639008-10-9

• 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: N-{4-[2-(benzylmethylsulfamoyl)ethyl]phenyl}-N-(2,2-dimethoxyethyl)-2,2,2-trifluoroacetamide
• 英文别名: N-[4-[2-[benzyl(methyl)sulfamoyl]ethyl]phenyl]-N-(2,2-dimethoxyethyl)-2,2,2-trifluoroacetamide
• CAS: 639008-10-9
• 化学式: C₂₂H₂₇F₃N₂O₅S
• 分子量: 488.528
• InChiKey: ILCNTEFPYQQJAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  563.5±60.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-{4-[2-(benzylmethylsulfamoyl)ethyl]phenyl}-N-(2,2-dimethoxyethyl)-2,2,2-trifluoroacetamide 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 sodium 、 四氯化钛 作用下， 以 四氢呋喃 、 甲醇 、 氨 、 氯苯 为溶剂， -78.0~110.0 ℃ 、500.0 kPa 条件下， 反应 17.03h， 生成 那拉曲坦
  参考文献：
  名称：

  Synthesis of 5-Substituted Indole Derivatives. Part 4: Naratriptan from α-Anilinoacetaldehyde Dimethylacetal by TiCl4-Mediated Cyclisation

  摘要：

  N-Methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide (Naratriptan, 2) was prepared from N-methyl-N-phenylmethyl-2-(4-aminophenyl)ethanesulfonamide (3b) through reductive alkylation with dimethoxyacetaldehyde followed by N-acylation and TiCl4-mediated indolisation, according to Sundberg procedure. The isopropyl group proved to be a useful protecting group for sulfonate esters in a number of transformations but was cleaved in the presence of TiCl4.

  DOI：

  10.3987/com-03-9838
• 作为产物：
  描述：

  2-(4-nitrophenyl)ethenesulfonic acid benzylmethylamide 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 51.0h， 生成 N-{4-[2-(benzylmethylsulfamoyl)ethyl]phenyl}-N-(2,2-dimethoxyethyl)-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  Synthesis of 5-Substituted Indole Derivatives. Part 4: Naratriptan from α-Anilinoacetaldehyde Dimethylacetal by TiCl4-Mediated Cyclisation

  摘要：

  N-Methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide (Naratriptan, 2) was prepared from N-methyl-N-phenylmethyl-2-(4-aminophenyl)ethanesulfonamide (3b) through reductive alkylation with dimethoxyacetaldehyde followed by N-acylation and TiCl4-mediated indolisation, according to Sundberg procedure. The isopropyl group proved to be a useful protecting group for sulfonate esters in a number of transformations but was cleaved in the presence of TiCl4.

  DOI：

  10.3987/com-03-9838

文献信息

• Synthesis of 5-Substituted Indole Derivatives. Part 4: Naratriptan from α-Anilinoacetaldehyde Dimethylacetal by TiCl4-Mediated Cyclisation
  作者：Béla Pete、Gyula Simig、László Poszávácz、László Toke

  DOI：10.3987/com-03-9838

  日期：——

  N-Methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide (Naratriptan, 2) was prepared from N-methyl-N-phenylmethyl-2-(4-aminophenyl)ethanesulfonamide (3b) through reductive alkylation with dimethoxyacetaldehyde followed by N-acylation and TiCl4-mediated indolisation, according to Sundberg procedure. The isopropyl group proved to be a useful protecting group for sulfonate esters in a number of transformations but was cleaved in the presence of TiCl4.