2-Phenyl-5-(1'-hydroxy-2',2',2'-trifluoroethyl)pyrrole | 78028-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-Phenyl-5-(1'-hydroxy-2',2',2'-trifluoroethyl)pyrrole
• 英文别名: 2,2,2-trifluoro-1-(5-phenylpyrrol-2-yl)-1-ethanol；1-(5-Phenyl-1H-pyrrole-2-yl)-2,2,2-trifluoroethanol；2,2,2-trifluoro-1-(5-phenyl-1H-pyrrol-2-yl)ethanol
• CAS: 78028-28-1
• 化学式: C₁₂H₁₀F₃NO
• 分子量: 241.213
• InChiKey: PTRZGKGPIMNGMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Phenyl-5-(1'-hydroxy-2',2',2'-trifluoroethyl)pyrrole 在 四磷十氧化物 、 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 2.17h， 生成 4,4'-difluoro-3-phenyl-8-trifluoromethyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  General Route to Symmetric and Asymmetric meso-CF₃-3(5)-Aryl(hetaryl)- and 3,5-Diaryl(dihetaryl)-BODIPY Dyes

  摘要：

  A general efficient route to hitherto inaccessible symmetric and asymmetric meso-CF3-BODIPY dyes has been developed. The key stages Include the reduction of available 2-trifluoroacetylpyrroles to the corresponding alcohols which are further condensed with pyrroles. The method allows the BODIPY with 3(5)aryl(hetaryl) and 3,5-diaryl(hetaryl) substituents to be readily assembled. The BODIPY dyes synthesized fluoresce (Phi(f) = 0.56-1.00) in the 560-680 nm region.

  DOI：

  10.1021/ol200360f
• 作为产物：
  描述：

  2-苯基-吡咯 在 吡啶 、 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 3.17h， 生成 2-Phenyl-5-(1'-hydroxy-2',2',2'-trifluoroethyl)pyrrole
  参考文献：
  名称：

  General Route to Symmetric and Asymmetric meso-CF₃-3(5)-Aryl(hetaryl)- and 3,5-Diaryl(dihetaryl)-BODIPY Dyes

  摘要：

  A general efficient route to hitherto inaccessible symmetric and asymmetric meso-CF3-BODIPY dyes has been developed. The key stages Include the reduction of available 2-trifluoroacetylpyrroles to the corresponding alcohols which are further condensed with pyrroles. The method allows the BODIPY with 3(5)aryl(hetaryl) and 3,5-diaryl(hetaryl) substituents to be readily assembled. The BODIPY dyes synthesized fluoresce (Phi(f) = 0.56-1.00) in the 560-680 nm region.

  DOI：

  10.1021/ol200360f

文献信息

• Application of meso-CF3-Fluorophore BODIPY with Phenyl and Pyrazolyl Substituents for Lifetime Visualization of Lysosomes
  作者：Irina S. Trukhan、Denis N. Tomilin、Nataliya N. Dremina、Lyubov N. Sobenina、Michael G. Shurygin、Konstantin B. Petrushenko、Igor K. Petrushenko、Boris A. Trofimov、Irina A. Shurygina

  DOI：10.3390/molecules27155018

  日期：——

  A bright far-red emitting unsymmetrical meso-CF3-BODIPY fluorescent dye with phenyl and pyrazolyl substituents was synthesized by condensation of trifluoropyrrolylethanol with pyrazolyl-pyrrole, with subsequent oxidation and complexation of the formed dipyrromethane. This BODIPY dye exhibits optical absorption at λab ≈ 610–620 nm and emission at λem ≈ 640–650 nm. The BODIPY was studied on Ehrlich carcinoma cells as a lysosome-specific fluorescent dye that allows intravital staining of cell structures with subsequent real-time monitoring of changes occurring in the cells. It was also shown that the rate of uptake by cells, the rate of intracellular transport into lysosomes, and the rate of saturation of cells with the dye depend on its concentration in the culture medium. A concentration of 5 μM was chosen as the most suitable BODIPY concentration for fluorescent staining of living cell lysosomes, while a concentration of 100 μM was found to be toxic to Ehrlich carcinoma cells.

  通过三氟吡咯乙醇与吡唑-吡咯的缩合，以及随后对形成的二吡咯甲烷进行氧化和络合，合成了一种具有苯基和吡唑取代基的明亮远红发射非对称介-CF3-BODIPY 荧光染料。这种 BODIPY 染料的光吸收波长为 λab ≈ 610-620 纳米，发射波长为 λem ≈ 640-650 纳米。BODIPY 作为一种溶酶体特异性荧光染料，可对细胞结构进行眼内染色，随后实时监测细胞内发生的变化。研究还表明，细胞对这种染料的吸收率、进入溶酶体的细胞内转运率以及细胞的饱和率都取决于其在培养液中的浓度。5 μM 的浓度被选为对活细胞溶酶体进行荧光染色最合适的 BODIPY 浓度，而 100 μM 的浓度则对艾氏癌细胞有毒性。
• Synthesis and antimicrobial activity of some pyrroles
  作者：B. A. Trofimov、A. I. Mikhaleva、A. I. Belyaevskii、N. A. Volyanskaya、S. E. Korostova、L. N. Balabanova、A. N. Vasil'ev、Yu. L. Volyanskii

  DOI：10.1007/bf00758457

  日期：1981.3
• General Route to Symmetric and Asymmetric <i>meso</i>-CF₃-3(5)-Aryl(hetaryl)- and 3,5-Diaryl(dihetaryl)-BODIPY Dyes
  作者：Lubov N. Sobenina、Alexander M. Vasil’tsov、Olga V. Petrova、Konstantin B. Petrushenko、Igor A. Ushakov、Gilles Clavier、Rachel Meallet-Renault、Albina I. Mikhaleva、Boris A. Trofimov

  DOI：10.1021/ol200360f

  日期：2011.5.20

  A general efficient route to hitherto inaccessible symmetric and asymmetric meso-CF3-BODIPY dyes has been developed. The key stages Include the reduction of available 2-trifluoroacetylpyrroles to the corresponding alcohols which are further condensed with pyrroles. The method allows the BODIPY with 3(5)aryl(hetaryl) and 3,5-diaryl(hetaryl) substituents to be readily assembled. The BODIPY dyes synthesized fluoresce (Phi(f) = 0.56-1.00) in the 560-680 nm region.