methyl 8-(4-methoxybenzoyl)-3-methyl-4-(trifluoromethyl)-3-azabicyclo[4.2.0]octa-1(8),5-diene-4-carboxylate | 1400553-31-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 8-(4-methoxybenzoyl)-3-methyl-4-(trifluoromethyl)-3-azabicyclo[4.2.0]octa-1(8),5-diene-4-carboxylate
• 英文别名: Methyl 8-(4-methoxybenzoyl)-3-methyl-4-(trifluoromethyl)-3-azabicyclo[4.2.0]octa-1(8),5-diene-4-carboxylate
• CAS: 1400553-31-2
• 化学式: C₁₉H₁₈F₃NO₄
• 分子量: 381.351
• InChiKey: SDIGYOSHNLGOHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 8-(4-methoxybenzoyl)-3-methyl-4-(trifluoromethyl)-3-azabicyclo[4.2.0]octa-1(8),5-diene-4-carboxylate 在 四氢吡咯 、 ammonium acetate 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 1.33h， 生成 methyl 2-(4-methoxyphenyl)-7-methyl-6-(trifluoromethyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-6-carboxylate
  参考文献：
  名称：

  Cyclobutene Ring-Opening of Bicyclo[4.2.0]octa-1,6-dienes: Access to CF₃-Substituted 5,6,7,8-Tetrahydro-1,7-naphthyridines

  摘要：

  An efficient method for the synthesis of novel CF3-substituted tetrahydro-1,7-naphthyridines including cyclic alpha-amino acid derivatives has been developed. The method is based on unusual cyclobutene ring-opening of bicyclo[4.2.0]octa-1,6-dienes with pyrrolidine to afford the corresponding 1,5-diketones followed by their heterocyclization. A convenient one-pot procedure has been also elaborated starting from readily available trifluoromethylated 1,6-allenynes.

  DOI：

  10.1021/jo301501r
• 作为产物：
  描述：

  methyl 2-[[4-(4-methoxyphenyl)-4-oxobut-2-yn-1-yl](methyl)amino]-2-(trifluoromethyl)penta-3,4-dienoate 以 甲苯 为溶剂， 反应 2.0h， 以89%的产率得到methyl 8-(4-methoxybenzoyl)-3-methyl-4-(trifluoromethyl)-3-azabicyclo[4.2.0]octa-1(8),5-diene-4-carboxylate
  参考文献：
  名称：

  Cyclobutene Ring-Opening of Bicyclo[4.2.0]octa-1,6-dienes: Access to CF₃-Substituted 5,6,7,8-Tetrahydro-1,7-naphthyridines

  摘要：

  An efficient method for the synthesis of novel CF3-substituted tetrahydro-1,7-naphthyridines including cyclic alpha-amino acid derivatives has been developed. The method is based on unusual cyclobutene ring-opening of bicyclo[4.2.0]octa-1,6-dienes with pyrrolidine to afford the corresponding 1,5-diketones followed by their heterocyclization. A convenient one-pot procedure has been also elaborated starting from readily available trifluoromethylated 1,6-allenynes.

  DOI：

  10.1021/jo301501r

文献信息

• Cyclobutene Ring-Opening of Bicyclo[4.2.0]octa-1,6-dienes: Access to CF₃-Substituted 5,6,7,8-Tetrahydro-1,7-naphthyridines
  作者：Artur K. Mailyan、Alexander S. Peregudov、Pierre H. Dixneuf、Christian Bruneau、Sergey N. Osipov

  DOI：10.1021/jo301501r

  日期：2012.10.5

  An efficient method for the synthesis of novel CF3-substituted tetrahydro-1,7-naphthyridines including cyclic alpha-amino acid derivatives has been developed. The method is based on unusual cyclobutene ring-opening of bicyclo[4.2.0]octa-1,6-dienes with pyrrolidine to afford the corresponding 1,5-diketones followed by their heterocyclization. A convenient one-pot procedure has been also elaborated starting from readily available trifluoromethylated 1,6-allenynes.