2-[1-(Toluene-4-sulfonyl)-1H-pyrrol-2-yl]-propionaldehyde | 199291-07-1

• 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: 2-[1-(Toluene-4-sulfonyl)-1H-pyrrol-2-yl]-propionaldehyde
• 英文别名: 2-[1-(4-Methylphenyl)sulfonylpyrrol-2-yl]propanal
• CAS: 199291-07-1
• 化学式: C₁₄H₁₅NO₃S
• 分子量: 277.344
• InChiKey: FOBKXUPMCXNKAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[1-(Toluene-4-sulfonyl)-1H-pyrrol-2-yl]-propionaldehyde 在 silver(l) oxide 作用下， 以50%的产率得到2-[1-(Toluene-4-sulfonyl)-1H-pyrrol-2-yl]-propionic acid
  参考文献：
  名称：

  Rhodium-Catalyzed Hydroformylation of 2-Vinyl- and 3-Vinyl-1-tosylpyrroles As a Convenient Synthetic Route to the Corresponding 2-(1-Tosylpyrrolyl)propanals and Derivatives

  摘要：

  2-(1-Tosylpyrrolyl)propanals 2a-b were conveniently prepared (70% yield) via rhodium-catalyzed hydroformylation of the corresponding 2-vinyl- and 3-vinyl-1-tosylpyrroles 1a-b and successfully transformed into some new derivatives (50-90% yield).

  DOI：

  10.1080/00397919708005459
• 作为产物：
  描述：

  1-(对甲苯磺酰)吡咯-2-甲醛 在 dodecacarbonyltetrarhodium(0) 作用下， 以 苯 为溶剂， 40.0 ℃ 、16.0 kPa 条件下， 反应 24.0h， 生成 2-[1-(Toluene-4-sulfonyl)-1H-pyrrol-2-yl]-propionaldehyde
  参考文献：
  名称：

  Rhodium-Catalyzed Hydroformylation of 2-Vinyl- and 3-Vinyl-1-tosylpyrroles As a Convenient Synthetic Route to the Corresponding 2-(1-Tosylpyrrolyl)propanals and Derivatives

  摘要：

  2-(1-Tosylpyrrolyl)propanals 2a-b were conveniently prepared (70% yield) via rhodium-catalyzed hydroformylation of the corresponding 2-vinyl- and 3-vinyl-1-tosylpyrroles 1a-b and successfully transformed into some new derivatives (50-90% yield).

  DOI：

  10.1080/00397919708005459

文献信息

• Influence of the reaction temperature on the regioselectivity in the rhodium-catalyzed hydroformylation of vinylpyrroles
  作者：Aldo Caiazzo、Roberta Settambolo、Gloria Uccello-Barretta、Raffaello Lazzaroni

  DOI：10.1016/s0022-328x(97)00479-8

  日期：1997.12

  The influence of the temperature on the regioselectivity in the hydroformylation of the vinylpyrrole isomers and of the corresponding N-tosylated substrates has been investigated in the range 20-100 degrees C, in the presence of Rh-4(CO)(12). Ar all the temperatures the branched aldehyde was prevailing with respect to the linear isomer for all the substrates (I cu-regioselectivity). With increasing temperature, an increase of the linear aldehyde was observed to a different extent in dependence on the substrate nature. H-2 NMR investigation of the crude reaction mixture recovered from deuterioformylation of 3-vinylpyrrole at partial substrate conversion points out that the observed depression of the alpha-regioselectivity with increasing temperature must be connected to a beta-hydride elimination process occurring for the branched alkyl-rhodium intermediates but not for the linear ones. (C) 1997 Elsevier Science S.A.
• Rhodium-Catalyzed Hydroformylation of 2-Vinyl- and 3-Vinyl-1-tosylpyrroles As a Convenient Synthetic Route to the Corresponding 2-(1-Tosylpyrrolyl)propanals and Derivatives
  作者：Roberta Settambolo、Aldo Caiazzo、Raffaello Lazzaroni

  DOI：10.1080/00397919708005459

  日期：1997.12

  2-(1-Tosylpyrrolyl)propanals 2a-b were conveniently prepared (70% yield) via rhodium-catalyzed hydroformylation of the corresponding 2-vinyl- and 3-vinyl-1-tosylpyrroles 1a-b and successfully transformed into some new derivatives (50-90% yield).