4-fluoro-4-methoxy-1,3,5,7-tetramethyl-2,6-diethyl-8-H-4-bora-3a,4a-diaza-s-indacene | 253169-80-1

• 英文名称: 4-fluoro-4-methoxy-1,3,5,7-tetramethyl-2,6-diethyl-8-H-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 4-fluoro-4-methoxy-1,3,5,7-tetramethyl-2,6-diethyl-8H-4-bora-3a,4a-diaza-s-indacene
• CAS: 253169-80-1
• 化学式: C₁₈H₂₆BFN₂O
• 分子量: 316.227
• InChiKey: NJXDBJZBUINSJM-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

• 作为反应物：
  描述：

  4-fluoro-4-methoxy-1,3,5,7-tetramethyl-2,6-diethyl-8-H-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75%的产率得到(2Z)-4-乙基-2-[(4-乙基-3,5-二甲基-1H-吡咯-2-基)亚甲基]-3,5-二甲基吡咯
  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：

  1,3,7,9-tetramethyl-2,8-diethyl-4,6-dipyrrin hydrobromide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.84h， 生成 4-fluoro-4-methoxy-1,3,5,7-tetramethyl-2,6-diethyl-8-H-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