4,4-dimethoxy-8-phenyl-1,3,5,7-tetramethyl-BODIPY | 915768-70-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4-dimethoxy-8-phenyl-1,3,5,7-tetramethyl-BODIPY
• 英文别名: 2,2-Dimethoxy-4,6,10,12-tetramethyl-8-phenyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 915768-70-6
• 化学式: C₂₁H₂₅BN₂O₂
• 分子量: 348.253
• InChiKey: XBOHIFDZAITMSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,3′,5,5′-tetramethyl-6-phenylpyrromethene 在 四氯苯醌 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 4,4-dimethoxy-8-phenyl-1,3,5,7-tetramethyl-BODIPY
  参考文献：
  名称：

  Convenient one-pot procedure for synthesizing 4,4′-dimethoxy-boradiaza-s-indacene dyes and their application to cell labeling

  摘要：

  We succeeded in developing a convenient one-pot pathway for synthesizing 4,4'-dimethoxy-boradiaza-s-indacene dyes 4a-d. The structures feature two methoxy groups in place of the fluorine atoms in 4,4'-difluoro-4-boradiaza-s-indacene. These novel dyes emitted green fluorescence and possessed moderate to high fluorescence quantum yields (Phi=0.32-0.93). We demonstrated that these dyes have applicability to cell labeling. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.043

文献信息

• Synthesis and Reactivity of 4,4-Dialkoxy-BODIPYs: An Experimental and Computational Study
  作者：Alex L. Nguyen、Petia Bobadova-Parvanova、Melissa Hopfinger、Frank R. Fronczek、Kevin M. Smith、M. Graça H. Vicente

  DOI：10.1021/ic502821m

  日期：2015.4.6

  A series of boron-disubstituted O-BODIPYs were synthesized, and their structures and spectroscopic properties were investigated using both computational and experimental methods. Three methods were investigated for the preparation of 4,4-dimethoxy-BODIPYs bearing electron-donating or electron-withdrawing 8-aryl groups: method A employs refluxing in the presence of NaOMe/MeOH, method B uses AlCl3 in refluxing dichloromethane followed by addition of methanol as nucleophile, and method C involves activation of the BODIPYs using TMSOTf in refluxing toluene followed by addition of methanol. The yields obtained depend on the method used and the structure of the starting BODIPYs; for example, 1a and 3a were most efficiently prepared using method C (98 and 70%, respectively), while 2a was best prepared by method A (50%). Methods B and C were employed for the synthesis of seven new 4,4-dialkoxy-BODIPYs. 4,4-Dipropargyloxy-BODIPY 1e reacted under Cu(I)-catalyzed alkyne-azide Huisgen cycloaddition conditions to produce 4,4-bis(1,2,3-triazole)-BODIPY 4 in 78% yield. The substitution of the fluorides for alkoxy groups on the BODIPYs had no significant effect on the absorption and emission wavelengths but altered their fluorescence quantum yields. Among this series of dialkoxy-BODIPYs, the 4,4-dipropargyloxy 1e and its corresponding bis(1,2,3-triazole) 4 show the largest quantum yields in toluene and THF, respectively.