methyl 2-(2-acetyl-1H-pyrrol-1-yl)benzoate | 1350077-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 2-(2-acetyl-1H-pyrrol-1-yl)benzoate
• 英文别名: Methyl 2-(2-acetylpyrrol-1-yl)benzoate；methyl 2-(2-acetylpyrrol-1-yl)benzoate
• CAS: 1350077-30-3
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: GBKBDDRCRIMXNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 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：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-acetyl-1H-pyrrol-1-yl)benzoate 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 氢气 、 三甲基乙酸 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 25.0h， 生成 (R)-4-methyl-5,6-dihydro-4H-benzo[f ]pyrrolo[1,2-a][1,4]-diazepine
  参考文献：
  名称：

  Developments in Meyers’ Lactamization Methodology: En Route to Bi(hetero)aryl Structures with Defined Axial Chirality

  摘要：

  Highly atroposelective Meyers' lactamization promoted by pivalic acid under microwave irradiation is reported which allows the construction of nonracemic substituted-dibenzo(di)azepine derivatives through a center to axial chirality transfer principle, controlling the otherwise configurationally labile biaryl axis. This approach provides a straightforward entry to enantioenriched analogues of biorelevant architectures.

  DOI：

  10.1021/jo401259w
• 作为产物：
  描述：

  2-乙酰基吡咯 、 2-碘苯甲酸甲酯 在 copper(l) iodide 、 potassium carbonate 、 (1R,2R)-(-)-N,N'-二甲基-1,2-环己二胺 作用下， 以 甲苯 为溶剂， 以71%的产率得到methyl 2-(2-acetyl-1H-pyrrol-1-yl)benzoate
  参考文献：
  名称：

  Developments in Meyers’ Lactamization Methodology: En Route to Bi(hetero)aryl Structures with Defined Axial Chirality

  摘要：

  Highly atroposelective Meyers' lactamization promoted by pivalic acid under microwave irradiation is reported which allows the construction of nonracemic substituted-dibenzo(di)azepine derivatives through a center to axial chirality transfer principle, controlling the otherwise configurationally labile biaryl axis. This approach provides a straightforward entry to enantioenriched analogues of biorelevant architectures.

  DOI：

  10.1021/jo401259w

文献信息

• Developments in Meyers’ Lactamization Methodology: En Route to Bi(hetero)aryl Structures with Defined Axial Chirality
  作者：Svetlana Postikova、Mohamad Sabbah、Daniel Wightman、Ich Tuan Nguyen、Morgane Sanselme、Thierry Besson、Jean-François Brière、Sylvain Oudeyer、Vincent Levacher

  DOI：10.1021/jo401259w

  日期：2013.8.16

  Highly atroposelective Meyers' lactamization promoted by pivalic acid under microwave irradiation is reported which allows the construction of nonracemic substituted-dibenzo(di)azepine derivatives through a center to axial chirality transfer principle, controlling the otherwise configurationally labile biaryl axis. This approach provides a straightforward entry to enantioenriched analogues of biorelevant architectures.