2-[4-(2,2-dimethoxyethylamino)phenyl]ethanesulfonic acid isopropyl ester | 639008-07-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[4-(2,2-dimethoxyethylamino)phenyl]ethanesulfonic acid isopropyl ester
• 英文别名: propan-2-yl 2-[4-(2,2-dimethoxyethylamino)phenyl]ethanesulfonate
• CAS: 639008-07-4
• 化学式: C₁₅H₂₅NO₅S
• 分子量: 331.433
• InChiKey: MBGRCKYBCKZFMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  22.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-[4-(2,2-dimethoxyethylamino)phenyl]ethanesulfonic acid isopropyl ester 在 四氯化钛 、 三乙胺 作用下， 以 氯苯 、 甲苯 为溶剂， 反应 33.08h， 生成 2-(1H-indol-5-yl)ethanesulfonic acid
  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-羟基-2-(4-硝基苯基)乙磺酸异丙酯 在 palladium on activated charcoal 氢气 、 甲基磺酰氯 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 氯仿 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 57.25h， 生成 2-[4-(2,2-dimethoxyethylamino)phenyl]ethanesulfonic acid isopropyl ester
  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.