1-acetyl-8-hydroxy-5,6,7,8-tetrahydroindolizine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-acetyl-8-hydroxy-5,6,7,8-tetrahydroindolizine
• 英文别名: 1-(8-Hydroxy-5,6,7,8-tetrahydroindolizin-1-yl)ethanone；1-(8-hydroxy-5,6,7,8-tetrahydroindolizin-1-yl)ethanone
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: XEZJHBGXSCIICF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-乙酰基吡咯 在 dodecacarbonyltetrarhodium(0) sodium hydroxide 、 一氧化碳 、 氢气 、 四丁基硫酸氢铵 作用下， 以 水 、 甲苯 为溶剂， 70.0~140.0 ℃ 、3.04 MPa 条件下， 反应 49.0h， 生成 1-acetyl-8-hydroxy-5,6,7,8-tetrahydroindolizine
  参考文献：
  名称：

  Domino reaction sequences in the rhodium-catalyzed hydroformylation of 3-acetyl-1-allylpyrrole: a short route to 5,6,7,8-tetrahydroindolizines

  摘要：

  When 3-acetyl-l-allylpyrrole (1) was subjected under hydroformylation conditions, with Rh-4(CO)(12) as catalyst precursor, to 30 atm CO/H-2 (1:1) total pressure and 140 degrees C, an equimolar mixture of the isomeric 5,6,7,8-tetrahydroindolizines 4' and 5' was obtained as the almost exclusive product. In both cases a domino hydroformylation/cyclization on the alpha pyrrole positions by the aldehyde 3 carbonyl group occurs which involves different intermediates: while 4' is generated via the dihydroindolizine 4, 5' forms via direct reduction of 8-hydroxytetrahydroindolizine 5, a structure that has never been observed before from 1-allylpyrroles under oxo conditions. (c) 2005 Published by Elsevier B.V.

  DOI：

  10.1016/j.jorganchem.2005.01.018

文献信息

• Domino reaction sequences in the rhodium-catalyzed hydroformylation of 3-acetyl-1-allylpyrrole: a short route to 5,6,7,8-tetrahydroindolizines
  作者：Silvia Rocchiccioli、Roberta Settambolo、Raffaello Lazzaroni

  DOI：10.1016/j.jorganchem.2005.01.018

  日期：2005.3

  When 3-acetyl-l-allylpyrrole (1) was subjected under hydroformylation conditions, with Rh-4(CO)(12) as catalyst precursor, to 30 atm CO/H-2 (1:1) total pressure and 140 degrees C, an equimolar mixture of the isomeric 5,6,7,8-tetrahydroindolizines 4' and 5' was obtained as the almost exclusive product. In both cases a domino hydroformylation/cyclization on the alpha pyrrole positions by the aldehyde 3 carbonyl group occurs which involves different intermediates: while 4' is generated via the dihydroindolizine 4, 5' forms via direct reduction of 8-hydroxytetrahydroindolizine 5, a structure that has never been observed before from 1-allylpyrroles under oxo conditions. (c) 2005 Published by Elsevier B.V.