1,3,5,7-tetramethyl-2,6-diethyl-8-H-4,4'-diethyl-bora-3a,4a-diaza-s-indacene | 69646-58-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1,3,5,7-tetramethyl-2,6-diethyl-8-H-4,4'-diethyl-bora-3a,4a-diaza-s-indacene
• 英文别名: 2,6,4,4-tetraethyl-1,3,5,7-tetramethyl-8H-3a,4a-diaza-4-bora-s-indacene；2,4,4,6-tetraethyl-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indecene
• CAS: 69646-58-8
• 化学式: C₂₁H₃₃BN₂
• 分子量: 324.317
• InChiKey: UVXHEMHUHOJEIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  1,3,5,7-tetramethyl-2,6-diethyl-8-H-4,4'-diethyl-bora-3a,4a-diaza-s-indacene 、 三氟化硼乙醚 以 二氯甲烷 为溶剂， 反应 0.25h， 以80%的产率得到2,6-diethyl-4,4-difluoro-1,3,5,7-tetramethyl-8H-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Masking and Demasking Strategies for the BF₂–BODIPYs as a Tool for BODIPY Fluorophores

  摘要：

  An efficient and chemoselective route for transforming BF(2)BODIPYs to Et2B-BODIPYs (masking) was developed using Et2AlCl. The Et groups can be easily replaced with F atoms using BF3 center dot Et2O in moist CH2Cl2 to regenerate the BF(2)BODIPYs (demasking). The maskingdemasking strategy is very useful for synthesizing functionalized BODIPYs via nucleophilic and reductive reactions. The masking strategy was used to synthesize a BODIPY dimer by McMurry coupling of a formyl Et2BBODIPY, while a new BODIPY with an asymmetrically substituted B-center was synthesized using the demasking strategy.

  DOI：

  10.1021/jo502028g
• 作为产物：
  描述：

  2,4,8,10-tetramethyl-3,9-diethyldipyrrolyl-5,7-methene 在 三氯化硼 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 4.0h， 生成 1,3,5,7-tetramethyl-2,6-diethyl-8-H-4,4'-diethyl-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Cl-BODIPYs: a BODIPY class enabling facile B-substitution

  摘要：

  与相应的 F-BODIPYs 相比，Cl-BODIPYs 能在无气无湿的条件下以高产率从二吡喃中合成，而且极易在硼上发生取代反应，从而为硼官能化 BODIPYs 开辟了一条新途径。

  DOI：

  10.1039/c1cc16351e

文献信息

• Activation and deprotection of F-BODIPYs using boron trihalides
  作者：Travis Lundrigan、T. Stanley Cameron、Alison Thompson

  DOI：10.1039/c4cc02706j

  日期：——

  The activation of F-BODIPYs with boron trihalides, followed by treatment with a nucleophile, effects facile substitution at boron; using water as the nucleophile promotes deprotective removal of the -BF2 moiety and thereby production of the corresponding parent dipyrrin salt in quantitative yield under extremely mild conditions.

  用三卤化硼激活F-BODIPYs，然后用亲核试剂处理，可以很容易地在硼上进行取代；使用水作为亲核试剂可促进-BF2部分的脱保护基去除，从而在极温和的条件下以定量收率生产相应的母体双吡啶盐。
• Conversion of <i>F</i>-BODIPYs to <i>Cl</i>-BODIPYs: Enhancing the Reactivity of <i>F</i>-BODIPYs
  作者：Travis Lundrigan、Alison Thompson

  DOI：10.1021/jo302277d

  日期：2013.1.18

  A new method for the synthesis of Cl-BODIPYs from F-BODIPYs is reported, merely requiring treatment of the F-BODIPY with boron trichloride. Cl-BODIPYs are exploited as synthetic intermediates generated in situ for the overall conversion of F-BODIPYs to O- and C-BODIPYs in high overall yields using a mild one-pot procedure. This route enables F-BODIPYs to be transformed into derivatives that are not accessible via the direct route, as demonstrated via the use of 1,3-propanediol.
• Masking and Demasking Strategies for the BF₂–BODIPYs as a Tool for BODIPY Fluorophores
  作者：Ankush B. More、Soumyaditya Mula、Shrikant Thakare、Nagaiyan Sekar、Alok K. Ray、Subrata Chattopadhyay

  DOI：10.1021/jo502028g

  日期：2014.11.21

  An efficient and chemoselective route for transforming BF(2)BODIPYs to Et2B-BODIPYs (masking) was developed using Et2AlCl. The Et groups can be easily replaced with F atoms using BF3 center dot Et2O in moist CH2Cl2 to regenerate the BF(2)BODIPYs (demasking). The maskingdemasking strategy is very useful for synthesizing functionalized BODIPYs via nucleophilic and reductive reactions. The masking strategy was used to synthesize a BODIPY dimer by McMurry coupling of a formyl Et2BBODIPY, while a new BODIPY with an asymmetrically substituted B-center was synthesized using the demasking strategy.
• Cl-BODIPYs: a BODIPY class enabling facile B-substitution
  作者：Travis Lundrigan、Sarah M. Crawford、T. Stanley Cameron、Alison Thompson

  DOI：10.1039/c1cc16351e

  日期：——

  Cl-BODIPYs, synthesized in high yields from dipyrrins under air- and moisture-free conditions, are extremely facile to substitution at boron compared to their corresponding F-BODIPYs, opening up a new route to BODIPYs functionalized at boron.

  与相应的 F-BODIPYs 相比，Cl-BODIPYs 能在无气无湿的条件下以高产率从二吡喃中合成，而且极易在硼上发生取代反应，从而为硼官能化 BODIPYs 开辟了一条新途径。