(Z)-methyl 2-(2-((4-ethyl-3-methyl-1H,1'H-[2,2'-bipyrrol]-5-yl)methylene)-3,5-dimethyl-2H-pyrrol-4-yl)acetate | 1365480-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (Z)-methyl 2-(2-((4-ethyl-3-methyl-1H,1'H-[2,2'-bipyrrol]-5-yl)methylene)-3,5-dimethyl-2H-pyrrol-4-yl)acetate
• CAS: 1365480-83-6
• 化学式: C₂₁H₂₅N₃O₂
• 分子量: 351.448
• InChiKey: ZPZORWFNLVULOR-WQRHYEAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.24
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4,4-difluoro-1-ethyl-2,5,7-trimethyl-3-(N-Boc-pyrrolyl)-6-(methylethanoate)-8-H-4-bora-3a,4a-diaza-s-indacene 在 硫酸 、 水 、 potassium hydroxide 、 叔丁醇 作用下， 反应 3.25h， 生成 (Z)-methyl 2-(2-((4-ethyl-3-methyl-1H,1'H-[2,2'-bipyrrol]-5-yl)methylene)-3,5-dimethyl-2H-pyrrol-4-yl)acetate
  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