3-(α,α-dimethoxyethyl)-1-tosylindole | 904694-73-1

• 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: 3-(α,α-dimethoxyethyl)-1-tosylindole
• CAS: 904694-73-1
• 化学式: C₁₉H₂₁NO₄S
• 分子量: 359.446
• InChiKey: DGPUKJYUZDYDSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  57.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(α,α-dimethoxyethyl)-1-tosylindole 在 potassium hydrogensulfate 、 硫酸 、 氧气 作用下， 以 乙醇 、 甲苯 为溶剂， 20.0~100.0 ℃ 、1.86 kPa 条件下， 反应 72.5h， 生成 (3aRS,10bRS)-2-methyl-10-tosyl-3a,4,10,10b-tetrahydropyrrolo[3,4-a]carbazole-1,3,5-trione
  参考文献：
  名称：

  Substituted Pyrrolo[3,4-a]carbazoles from Reactions between 3-(1-Methoxy-vinyl)indoles and Maleimides

  摘要：

  5-Methylenolether derivatives of pyrrolo[3,4-a]carbazoles were obtained from cycloadditions between 3-(1-methoxyvinyl)-1-tosylindole and N-substituted maleimides. They were transformed into the hydroxy derivatives by treatment with H2SO4, selectively reduced to the ether by H-2/Pd-C, and in the imide moiety by L-Selectride(R). From the analogous BOC protected indole derivative the parent alpha,beta-unsaturated ketones were obtained, which were transformed into hydroxyimino compounds, and which could be deprotected by heating to the melting point. Deprotection of the tosyl derivatives was not successful. The imide part of the molecule was hydrolyzed using methanolic NaOH. The stereochemistry of all products Was elucidated mainly by spectroscopic methods, and compared with results of calculations.

  DOI：

  10.1007/s00706-005-0363-2
• 作为产物：
  描述：

  1H-吲哚,3-乙酰基-1-[(4-甲基苯基)磺酰]- 、 原甲酸三甲酯 在 甲烷磺酸 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以93%的产率得到3-(α,α-dimethoxyethyl)-1-tosylindole
  参考文献：
  名称：

  Substituted Pyrrolo[3,4-a]carbazoles from Reactions between 3-(1-Methoxy-vinyl)indoles and Maleimides

  摘要：

  5-Methylenolether derivatives of pyrrolo[3,4-a]carbazoles were obtained from cycloadditions between 3-(1-methoxyvinyl)-1-tosylindole and N-substituted maleimides. They were transformed into the hydroxy derivatives by treatment with H2SO4, selectively reduced to the ether by H-2/Pd-C, and in the imide moiety by L-Selectride(R). From the analogous BOC protected indole derivative the parent alpha,beta-unsaturated ketones were obtained, which were transformed into hydroxyimino compounds, and which could be deprotected by heating to the melting point. Deprotection of the tosyl derivatives was not successful. The imide part of the molecule was hydrolyzed using methanolic NaOH. The stereochemistry of all products Was elucidated mainly by spectroscopic methods, and compared with results of calculations.

  DOI：

  10.1007/s00706-005-0363-2