4,4-difluoro-1,3,5,7-tetramethyl-2-triuoroethanol-6-ethyl-4-bora-3a,4a-diaza-s-indacene | 1219789-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4,4-difluoro-1,3,5,7-tetramethyl-2-triuoroethanol-6-ethyl-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 4,4-difluoro-1,3,5,7-tetramethyl-2-(2,2,2-trifluoroethanol)-6-ethyl-8-H-4-bora-3a,4a-diaza-s-indacene；1-(11-Ethyl-2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-5-yl)-2,2,2-trifluoroethanol
• CAS: 1219789-02-2
• 化学式: C₁₇H₂₀BF₅N₂O
• 分子量: 374.162
• InChiKey: ZXEHUKFPLWBTFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,4-difluoro-1,3,5,7-tetramethyl-2-triuoroethanol-6-ethyl-4-bora-3a,4a-diaza-s-indacene 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 0.67h， 以93%的产率得到(Z)-1-(2-((4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-3,5-dimethyl-2H-pyrrol-4-yl)-2,2,2-trifluoroethanol
  参考文献：
  名称：

  Conversion of 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) to Dipyrrins with a Microwave-Promoted Deprotection Strategy

  摘要：

  4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) have been deprotected to give the corresponding free-base dipyrrins by heating a solution of the F-BODIPY In tert-butanol under 600 W of microwave irradiation in the presence of 6 equiv of potassium tert-butoxide for 40 min at 92 degrees C. Investigations of BODIPY modification at the meso position have also been undertaken and a meso-butyl product has been isolated.

  DOI：

  10.1021/ol902908j
• 作为产物：
  描述：

  2,3-dimethyl-4-(2,2-2-trifluoroethyl-1-hydroxy)-5-(3,5-dimethyl-4-ethylpyrrol-2-ylmethylidene)pyrrole hydrobromide 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， 生成 4,4-difluoro-1,3,5,7-tetramethyl-2-triuoroethanol-6-ethyl-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

文献信息

• Facile deprotection of F-BODIPYs using methylboronic acid
  作者：Craig D. Smith、Alison Thompson

  DOI：10.1039/d0ra05151a

  日期：——

  Removal of the –BF₂ moiety from F-BODIPYs using methylboronic acid provides a mild (de)protection strategy for dipyrrins.

  使用甲基硼酸从F-BODIPYs中去除-BF2基团为双吡啶提供了一种温和的（去）保护策略。
• Conversion of 4,4-Difluoro-4-bora-3a,4a-diaza-<i>s</i>-indacenes <b>(</b><i>F</i>-BODIPYs) to Dipyrrins with a Microwave-Promoted Deprotection Strategy
  作者：Sarah M. Crawford、Alison Thompson

  DOI：10.1021/ol902908j

  日期：2010.4.2

  4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) have been deprotected to give the corresponding free-base dipyrrins by heating a solution of the F-BODIPY In tert-butanol under 600 W of microwave irradiation in the presence of 6 equiv of potassium tert-butoxide for 40 min at 92 degrees C. Investigations of BODIPY modification at the meso position have also been undertaken and a meso-butyl product has been isolated.
• Use of <i>F</i>-BODIPYs as a Protection Strategy for Dipyrrins: Optimization of BF₂ Removal
  作者：Deborah A. Smithen、Alexander E. G. Baker、Matthew Offman、Sarah M. Crawford、T. Stanley Cameron、Alison Thompson

  DOI：10.1021/jo3002003

  日期：2012.4.6

  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.