1-(5,6,7,8-tetrahydroindolizin-2-yl)ethan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5,6,7,8-tetrahydroindolizin-2-yl)ethan-1-one
• 英文别名: 2-acetyl-5,6,7,8-tetrahydroindolizine；1-(5,6,7,8-tetrahydroindolizin-2-yl)ethanone
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: HTNIBBSPHQPTTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 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：
  22
• 氢给体数：
  0
• 氢受体数：
  1

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-(5,6,7,8-tetrahydroindolizin-2-yl)ethan-1-one
  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

• Antibacterial compounds
  申请人：Janssen Sciences Ireland UC

  公开号：US10364232B2

  公开（公告）日：2019-07-30

  The present invention relates to the following compounds wherein the integers are as defined in the description, and where the compounds may be useful as medicaments, for instance for use in the treatment of tuberculosis.

  本发明涉及以下化合物 其中的整数如描述中所定义，这些化合物可用作药物，例如用于治疗结核病。
• A novel photochemical synthesis of pyrroles from β-ketovinylogous amides
  作者：Jeffrey D. Winkler、Miles G. Siegel

  DOI：10.1016/s0040-4039(00)61542-3

  日期：1993.11

  Irradiation of beta-ketovinylogous amides leads to the formation of 3-acylpyrroles. A mechanistic rationale is offered which involves the recombination of a photochemically generated biradical, followed by transannular condensation to give the observed pyrrole product.
• Antibacterial Compounds
  申请人：Janssen Sciences Ireland UC

  公开号：US20180186768A1

  公开（公告）日：2018-07-05

  The present invention relates to the following compounds wherein the integers are as defined in the description, and where the compounds may be useful as medicaments, for instance for use in the treatment of tuberculosis.
• ANTIBACTERIAL COMPOUNDS
  申请人：Janssen Sciences Ireland UC

  公开号：US20190330189A1

  公开（公告）日：2019-10-31

  The present invention relates to the following compounds wherein the integers are as defined in the description, and where the compounds may be useful as medicaments, for instance for use in the treatment of tuberculosis.
• 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.