4,4-dimethoxy-1,3,5,7-tetramethyl-2,6-diethyl-8-H-4-bora-3a,4a-diaza-s-indacene | 250372-46-4

• 英文名称: 4,4-dimethoxy-1,3,5,7-tetramethyl-2,6-diethyl-8-H-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 1,3,5,7-tetramethyl-2,6-diethyl-8-H-4,4'-dimethoxy-bora-3a,4a-diaza-s-indacene；4,4-dimethoxy-1,3,5,7-tetramethyl-2,6-diethyl-8H-4-bora-3a,4a-diaza-s-indacene
• CAS: 250372-46-4
• 化学式: C₁₉H₂₉BN₂O₂
• 分子量: 328.262
• InChiKey: JSYKUFOWJGEUGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  2,6-diethyl-4,4-difluoro-1,3,5,7-tetramethyl-8H-4-bora-3a,4a-diaza-s-indacene 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4,4-dimethoxy-1,3,5,7-tetramethyl-2,6-diethyl-8-H-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Conversion of F-BODIPYs to Cl-BODIPYs: Enhancing the Reactivity of F-BODIPYs

  摘要：

  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.

  DOI：

  10.1021/jo302277d

文献信息

• 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。
• 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.