(Z)-1-(2-((4-acetyl-3,5-dimethyl-1H-pyrrol-2-yl)(phenyl)-methylene)-3,5-dimethyl-2H-pyrrol-4-yl)ethanone | 1365480-74-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-1-(2-((4-acetyl-3,5-dimethyl-1H-pyrrol-2-yl)(phenyl)-methylene)-3,5-dimethyl-2H-pyrrol-4-yl)ethanone
• 英文别名: 1-[(5Z)-5-[(4-acetyl-3,5-dimethyl-1H-pyrrol-2-yl)-phenylmethylidene]-2,4-dimethylpyrrol-3-yl]ethanone
• CAS: 1365480-74-5
• 化学式: C₂₃H₂₄N₂O₂
• 分子量: 360.456
• InChiKey: MKXMUPDBABUEDN-LNVKXUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-1-(2-((4-acetyl-3,5-dimethyl-1H-pyrrol-2-yl)(phenyl)-methylene)-3,5-dimethyl-2H-pyrrol-4-yl)ethanone 在 三乙胺 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 以21%的产率得到4,4-difluoro-1,3,5,7-tetramethyl-2,6-diacetyl-8-phenyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Use of F-BODIPYs as a Protection Strategy for Dipyrrins: Optimization of BF₂ Removal

  摘要：

  We recently reported the first general method for the deprotection of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) involving a microwave-assisted procedure for the removal of the BF2 moiety, and liberation of the corresponding free-base dipyrrin. Further optimization of the reaction has resulted in a more convenient and accessible protocol. The availability of this new methodology enables BF2-complexation to be used as a dipyrrin protection strategy. Herein lies a detailed examination of the deprotection reaction, with a view to optimization and gaining mechanistic insight, and its application in facilitating a multistep synthesis of pyrrolyldipyrrins.

  DOI：

  10.1021/jo3002003
• 作为产物：
  描述：

  4,4-difluoro-1,3,5,7-tetramethyl-2,6-diacetyl-8-phenyl-4-bora-3a,4a-diaza-s-indacene 在 水 、 potassium hydroxide 、 叔丁醇 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.25h， 以45%的产率得到(Z)-1-(2-((4-acetyl-3,5-dimethyl-1H-pyrrol-2-yl)(phenyl)-methylene)-3,5-dimethyl-2H-pyrrol-4-yl)ethanone
  参考文献：
  名称：

  Use of F-BODIPYs as a Protection Strategy for Dipyrrins: Optimization of BF₂ Removal

  摘要：

  We recently reported the first general method for the deprotection of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) involving a microwave-assisted procedure for the removal of the BF2 moiety, and liberation of the corresponding free-base dipyrrin. Further optimization of the reaction has resulted in a more convenient and accessible protocol. The availability of this new methodology enables BF2-complexation to be used as a dipyrrin protection strategy. Herein lies a detailed examination of the deprotection reaction, with a view to optimization and gaining mechanistic insight, and its application in facilitating a multistep synthesis of pyrrolyldipyrrins.

  DOI：

  10.1021/jo3002003