2,3-dimethyl-4-(2,2-2-trifluoroethyl-1-hydroxy)-5-(3,5-dimethyl-4-ethylpyrrol-2-ylmethylidene)pyrrole hydrobromide | 1093656-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 2,3-dimethyl-4-(2,2-2-trifluoroethyl-1-hydroxy)-5-(3,5-dimethyl-4-ethylpyrrol-2-ylmethylidene)pyrrole hydrobromide
• CAS: 1093656-43-9
• 化学式: BrH*C₁₇H₂₁F₃N₂O
• 分子量: 407.274
• InChiKey: NGSXPRLZRDLIJJ-NTISSMGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  48.38
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,3-dimethyl-4-(2,2-2-trifluoroethyl-1-hydroxy)-5-(3,5-dimethyl-4-ethylpyrrol-2-ylmethylidene)pyrrole hydrobromide 在 水 、 三乙胺 、 potassium hydroxide 、 叔丁醇 作用下， 以 二氯甲烷 为溶剂， 反应 2.42h， 生成 (Z)-1-(5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)-methyl)-2,4-dimethyl-1H-pyrrol-3-yl)-2,2,2-trifluoroethanol
  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

文献信息

• Synthesis of dipyrrins bearing chirality adjacent to the conjugated skeleton — Electron-poor pyrroles exhibit dramatically reduced nucleophilicity
  作者：Cory S Beshara、Beth M Pearce、Alison Thompson

  DOI：10.1139/v08-101

  日期：2008.10.1

  With the aim of furthering our investigations into the asymmetric complexation of dipyrrinato ligands, a dipyrrin bearing a stereogenic centre directly adjacent to the conjugated skeleton was synthesized. The electron-withdrawing nature of the chiral 4-(2,2,2-trifluoro-1-hydroxyethyl)- substituent significantly reduced the nucleophilicity of corresponding pyrroles, such that 2,2′-symmetrically substituted bis(dipyrrin)s bearing this motif were inaccessible. Furthermore, solutions of mononuclear dipyrrinato complexes were found to be less stable to acid-catalyzed decomplexation than the corresponding dinuclear complexes.Key words: dipyrrin, dipyrromethene, complexation, electron-poor pyrrole, chirality.

  为了进一步研究二吡咯配体的不对称络合，我们合成了一种二吡咯啉，其立体中心与共轭骨架直接相邻。手性 4-(2,2,2-三氟-1-羟乙基)取代基的吸电子特性大大降低了相应吡咯的亲核性，因此含有该基团的 2,2′-对称取代的双(二吡咯啉)无法进入。此外，与相应的双核配合物相比，单核二吡咯烷配合物溶液在酸催化下的解络合稳定性较差。