(4-methoxyphenyl)-[5-[(2,3,4,5,6-pentafluorophenyl)-pyrrol-2-ylidenemethyl]-1H-pyrrol-2-yl]methanone | 1437319-56-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-methoxyphenyl)-[5-[(2,3,4,5,6-pentafluorophenyl)-pyrrol-2-ylidenemethyl]-1H-pyrrol-2-yl]methanone
• CAS: 1437319-56-6
• 化学式: C₂₃H₁₃F₅N₂O₂
• 分子量: 444.36
• InChiKey: QVHZPBYKRDBFGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  54.45
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4-methoxyphenyl)-[5-[(2,3,4,5,6-pentafluorophenyl)-pyrrol-2-ylidenemethyl]-1H-pyrrol-2-yl]methanone 、 zinc(II) acetate dihydrate 以 甲醇 为溶剂， 反应 0.5h， 以83%的产率得到
  参考文献：
  名称：

  α-Monoacylated and α,α′- and α,β′-Diacylated Dipyrrins as Highly Sensitive Fluorescence “Turn-on” Zn²⁺ Probes

  摘要：

  With the purpose of developing readily synthesized CHEF (chelation-enhanced fluorescence) type Zn2+ probes with relatively simple molecular structures and excellent sensing behavior, p-anisoyl chloride was used for the acylation of 5-(pentafluorophenyl)dipyrromethane. Interestingly, the alpha,beta'-diacylated product PS2 with a unique substitution mode was obtained in high yield in addition to the normal a-substituted mono- and diacylated products PSI and PS3. Further oxidation of PS1-PS3 afforded dipyrrins S1-S3. Crystal structure and H-1 NMR measurements of S2 demonstrate the existence of a pure tautomer, which is consistent with DFT calculations. S1-S3 show highly Zn2+ selective "turn-on" fluorescence based on a CHEF mechanism by the formation of 2:1 (probe:metal) Zn2+ complexes. The emission colors can be easily tuned from green to red by changing the dipyrrin substitution modes. Furthermore, these probes demonstrate fast responses and wide applicable pH ranges. Among them, S2 shows the highest Zn2+ sensitivity, with a detection limit of 4.4 x 10(-8) M.

  DOI：

  10.1021/jo400454e
• 作为产物：
  描述：

  1-(4-methoxybenzoyl)-5-(pentafluorophenyl)dipyrromethane 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以61%的产率得到(4-methoxyphenyl)-[5-[(2,3,4,5,6-pentafluorophenyl)-pyrrol-2-ylidenemethyl]-1H-pyrrol-2-yl]methanone
  参考文献：
  名称：

  α-Monoacylated and α,α′- and α,β′-Diacylated Dipyrrins as Highly Sensitive Fluorescence “Turn-on” Zn²⁺ Probes

  摘要：

  With the purpose of developing readily synthesized CHEF (chelation-enhanced fluorescence) type Zn2+ probes with relatively simple molecular structures and excellent sensing behavior, p-anisoyl chloride was used for the acylation of 5-(pentafluorophenyl)dipyrromethane. Interestingly, the alpha,beta'-diacylated product PS2 with a unique substitution mode was obtained in high yield in addition to the normal a-substituted mono- and diacylated products PSI and PS3. Further oxidation of PS1-PS3 afforded dipyrrins S1-S3. Crystal structure and H-1 NMR measurements of S2 demonstrate the existence of a pure tautomer, which is consistent with DFT calculations. S1-S3 show highly Zn2+ selective "turn-on" fluorescence based on a CHEF mechanism by the formation of 2:1 (probe:metal) Zn2+ complexes. The emission colors can be easily tuned from green to red by changing the dipyrrin substitution modes. Furthermore, these probes demonstrate fast responses and wide applicable pH ranges. Among them, S2 shows the highest Zn2+ sensitivity, with a detection limit of 4.4 x 10(-8) M.

  DOI：

  10.1021/jo400454e