4,4-difluoro-8-(5-(8-hydroxyquinoline))-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene | 1296130-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4,4-difluoro-8-(5-(8-hydroxyquinoline))-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 4,4-difluoro-8-(8-hydroxyquinolin-5-yl)-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene；5-(2,2-Difluoro-4,12-dimethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)quinolin-8-ol
• CAS: 1296130-57-8
• 化学式: C₂₀H₁₆BF₂N₃O
• 分子量: 363.174
• InChiKey: GVJMWISZXFDFFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  41.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,4-difluoro-8-(5-(8-hydroxyquinoline))-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 重水 、 乙腈 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  萘甲酸修饰的Cu2 +检测Bodipy传感器，其荧光开-关性能不受分子配置的影响。

  摘要：

  用8-羟基喹啉-萘甲酸酯部分修饰的两个新的硼二吡咯烷酮，即4,4-二氟-8-（5-（5-（8-羟基喹啉-萘甲酸酯））-3,5-二甲基-4-硼-3a，4a-二氮杂-s-茚并四烯（8-HQ-N-DMe-Bodipy）（1）和4,4-二氟-8-（5-（8-羟基喹啉-萘甲酸酯））-1,3,5,7-四甲基-4合成了-硼-3a，4a-二氮杂-s-茚并茂（8-HQ-N-TMe-Bodipy）（2）。单晶X射线衍射分析揭示了这两种化合物中8-羟基喹啉-萘甲酸酯部分的非常相似的空间排列，尽管CCOC桥的扭转角分别为174.15和171.81°（分别为1和2），但尽管存在不同，但仍显示出相似的空间排列由于空间位阻，喹啉部分与Bodipy荧光团之间的二面角分别为1（73.46°）和2（82.26°），这是由于后者的Bodipy核上的C-1 / C-7甲基取代基引起的。系统光学研究揭示了红移吸收和荧光发射，以及相

  DOI：

  10.1016/j.saa.2016.12.034
• 作为产物：
  描述：

  8-羟基喹啉 在 三氟乙酸 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 4,4-difluoro-8-(5-(8-hydroxyquinoline))-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  8-Hydroxyquinoline-Substituted Boron–Dipyrromethene Compounds: Synthesis, Structure, and OFF–ON–OFF Type of pH-Sensing Properties

  摘要：

  A series of four novel 8-hydroxyquinoline-substituted boron-dipyrromethene derivatives, namely 4,4-difluoro-8-(5-(8-hydroxyquinoline))-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene (1), 4,4-difluoro-8-(5-(8-hydroxyquinoline))-1,3,5, 7-tetramethyl-4-bora-3a,4a-diaza-s-indacene (2), 4,4-difluoro-8-(5-azastyryl-(8-hydroxyquinoline))-3,5-dimethyl-4-bora-3a, 4a-diaza-s-indacene (3), and 4,4-difluoro-8-(5-azastyry1-(8-hydroxyquinoline))-1,3,5,7-tetramethyl-4-bora-3 a,4a-diaza-s-indacene (4), have been synthesized and characterized by a series of spectroscopic methods. The molecular structures of 1 and 2 have been determined by single-crystal X-ray diffraction analyses. The two methyl substituents attached at C-1 and C-7 positions of boron-dipyrromethene (Bodipy) in compound 2 was revealed to prevent the free rotation of the 8-hydroxyquinoline (8-HQ) moiety, resulting in an almost vertical 8-HQ-Bodipy configuration of this compound. This is obviously different from those for 1 with the dihedral angle between 8-hydroxyquinoline and Bodipy moieties of 65.44 and 66.79 degrees due to the lack of methyl substituents in the latter compound. The intense fluorescence from the Bodipy subunit of these compounds was revealed to gradually get diminished along with either decreasing or increasing the pH value under acidic and basic conditions, respectively, in particular for 1, 2, and 4 because of the photoinduced intramolecular electron transfer from excited Bodipy moiety to 8-HQ unit and just an opposite process. This renders these compounds the first OFF-ON-OFF type of pH-dependent fluorescent sensors. Nevertheless, both the intrinsic fluorescence of these compounds and their fluorescent quenching properties along with the change in the pH value have been found to depend on the steric configuration as well as the linking group between 8-hydroxyquinoline and Bodipy moieties, revealing the effect of molecular structure on their fluorescence properties.

  DOI：

  10.1021/jo200050a