2-(2-acetyl-1H-pyrrol-1-yl)-1-(4-methoxyphenyl)ethanone | 1418760-29-8

• 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-(4-methoxyphenyl)ethanone
• 英文别名: 2-(2-acetyl-1H-pyrrol-1-yl)-1-(4-methoxyphenyl)ethan-1-one；2-(2-Acetylpyrrol-1-yl)-1-(4-methoxyphenyl)ethanone；2-(2-acetylpyrrol-1-yl)-1-(4-methoxyphenyl)ethanone
• CAS: 1418760-29-8
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: TUKJTJJWNCXBCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-acetyl-1H-pyrrol-1-yl)-1-(4-methoxyphenyl)ethanone 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-(4-methoxyphenyl)indolizin-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 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以83%的产率得到2-(2-acetyl-1H-pyrrol-1-yl)-1-(4-methoxyphenyl)ethanone
  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

文献信息

• Domino [4 + 2] Annulation Access to Quinone–Indolizine Hybrids: Anticancer <i>N</i>-Fused Polycycles
  作者：Dirgha Raj Joshi、Yohan Seo、Yunkyung Heo、So-hyeon Park、Yechan Lee、Wan Namkung、Ikyon Kim

  DOI：10.1021/acs.joc.0c01291

  日期：2020.8.21

  A highly efficient synthetic route to new quinone-indolizine hybrids was accomplished from quinones and N-substituted pyrrole-2-carboxaldehydes via a domino Michael addition-aldol condensation-aromatization sequence through which the central pyridine ring was constructed in atom-economical and environment-friendly manner. Post modification of the resulting products was also demonstrated, enabling further expansion of this heterocyclic chemical space. Biological evaluation of the quinone-indolizine hybrids revealed potent anticancer effects in human prostate adenocarcinoma cells (PC-3) and oral adenosquamous carcinoma cells (CAL-27).
• 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.