8a-methyl-2-(3,5-dimethylphenyl)-3-(thiophen-3-yl)indolizin-1(8aH)-one | 1227746-49-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 8a-methyl-2-(3,5-dimethylphenyl)-3-(thiophen-3-yl)indolizin-1(8aH)-one
• 英文别名: 2-(3,5-Dimethylphenyl)-8a-methyl-3-thiophen-3-ylindolizin-1-one；2-(3,5-dimethylphenyl)-8a-methyl-3-thiophen-3-ylindolizin-1-one
• CAS: 1227746-49-7
• 化学式: C₂₁H₁₉NOS
• 分子量: 333.454
• InChiKey: HTMLWNPURZBYIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙酰基吡啶 在 四(三苯基膦)钯 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 13.33h， 生成 8a-methyl-2-(3,5-dimethylphenyl)-3-(thiophen-3-yl)indolizin-1(8aH)-one
  参考文献：
  名称：

  Palladium-catalyzed construction of poly-substituted indolizinones

  摘要：

  We have developed a highly efficient one-pot approach to poly-substituted indolizinones from tertiary propargylic alcohols by using a palladium-catalyzed domino reaction. This reaction is proposed to proceed via successive aminopalladation, reductive elimination, and 1,2-shift. While our previous effort to the same skeleton via 2-iodoindolizinones selected alpha,beta-unsaturated esters, terminal acetylenes, or boronic acids as coupling partners, this strategy introduces new functional groups at the C2 position of indolizinone core with (hetero)aryl halides or diallyl carbonate, expanding the substrate scope for decoration at the C2 site. Furthermore, a new preparation route to tertiary propargylic alcohols for this study is described to rapidly diversify the molecular framework. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.091

文献信息

• Expeditious Synthesis of Highly Substituted Indolizinones via a Palladium-Catalyzed Domino Sequence
  作者：Ikyon Kim、Kyungsun Kim

  DOI：10.1021/ol1006778

  日期：2010.6.4

  A direct one-pot approach to polysubstituted indolizinones from tertiary propargylic alcohols using a palladium-catalyzed domino process involving aminopalladation, reductive elimination, and 1,2-shift is described.
• Palladium-catalyzed construction of poly-substituted indolizinones
  作者：Hanyang Cho、Ikyon Kim

  DOI：10.1016/j.tet.2012.04.091

  日期：2012.7

  We have developed a highly efficient one-pot approach to poly-substituted indolizinones from tertiary propargylic alcohols by using a palladium-catalyzed domino reaction. This reaction is proposed to proceed via successive aminopalladation, reductive elimination, and 1,2-shift. While our previous effort to the same skeleton via 2-iodoindolizinones selected alpha,beta-unsaturated esters, terminal acetylenes, or boronic acids as coupling partners, this strategy introduces new functional groups at the C2 position of indolizinone core with (hetero)aryl halides or diallyl carbonate, expanding the substrate scope for decoration at the C2 site. Furthermore, a new preparation route to tertiary propargylic alcohols for this study is described to rapidly diversify the molecular framework. (c) 2012 Elsevier Ltd. All rights reserved.