2-(2-acetyl-1H-pyrrol-1-yl)-1-phenylethanone | 1418760-28-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-acetyl-1H-pyrrol-1-yl)-1-phenylethanone
• 英文别名: 2-(2-Acetylpyrrol-1-yl)-1-phenylethanone；2-(2-acetylpyrrol-1-yl)-1-phenylethanone
• CAS: 1418760-28-7
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: ZRQCIOMMYIJBMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-acetyl-1H-pyrrol-1-yl)-1-phenylethanone 在 potassium phosphate 、 四(三苯基膦)钯 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 methyl 4-(6-phenylindolizin-8-yl)benzoate
  参考文献：
  名称：

  Cycloaromatization Approach to Polysubstituted Indolizines from 2-Acetylpyrroles: Decoration of the Pyridine Unit

  摘要：

  A new synthetic route to indolizines with various substituents on the pyridine moiety was developed by utilizing a facile cycloaromatization of 2-acetylpyrrole derivatives. Without isolation, the resulting intermediates were allowed to react with various electrophiles to afford a range of indolizines. In particular, Suzuki-Miyaura cross-coupling of O-triflates with (hetero)arylboronic acids permitted introduction of diverse substituents at the C8 position of an indolizine skeleton.

  DOI：

  10.1021/jo302590a
• 作为产物：
  描述：

  2-乙酰基吡咯 、 2-溴苯乙酮 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 2-(2-acetyl-1H-pyrrol-1-yl)-1-phenylethanone
  参考文献：
  名称：

  Diversity-oriented decoration of pyrrolo[1,2-a]pyrazines

  摘要：

  Diversity-oriented synthesis of a chemical library based on a pyrrolo[1,2-a]pyrazine core is described by using palladium-catalyzed direct C6 arylation of pyrrolo[1,2-a]pyrazines with various aryl bromides. The starting materials, pyrrolo[1,2-a]pyrazines, were easily synthesized by the base-mediated N-alkylation of pyrrole-2-carboxaldehyde with several 2-bromoacetophenones followed by dehydrative cyclization with incorporation of nitrogen by the action of ammonium acetate. Introduction of other functional groups on this chemical scaffold is also discussed herein. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.08.003

文献信息

• Diversity-oriented decoration of pyrrolo[1,2-a]pyrazines
  作者：Sujin Park、Youngeun Jung、Ikyon Kim

  DOI：10.1016/j.tet.2014.08.003

  日期：2014.10

  Diversity-oriented synthesis of a chemical library based on a pyrrolo[1,2-a]pyrazine core is described by using palladium-catalyzed direct C6 arylation of pyrrolo[1,2-a]pyrazines with various aryl bromides. The starting materials, pyrrolo[1,2-a]pyrazines, were easily synthesized by the base-mediated N-alkylation of pyrrole-2-carboxaldehyde with several 2-bromoacetophenones followed by dehydrative cyclization with incorporation of nitrogen by the action of ammonium acetate. Introduction of other functional groups on this chemical scaffold is also discussed herein. (C) 2014 Elsevier Ltd. All rights reserved.
• Cycloaromatization Approach to Polysubstituted Indolizines from 2-Acetylpyrroles: Decoration of the Pyridine Unit
  作者：Jin Ho Lee、Ikyon Kim

  DOI：10.1021/jo302590a

  日期：2013.2.1

  A new synthetic route to indolizines with various substituents on the pyridine moiety was developed by utilizing a facile cycloaromatization of 2-acetylpyrrole derivatives. Without isolation, the resulting intermediates were allowed to react with various electrophiles to afford a range of indolizines. In particular, Suzuki-Miyaura cross-coupling of O-triflates with (hetero)arylboronic acids permitted introduction of diverse substituents at the C8 position of an indolizine skeleton.