2,2,3,3,4,4,4-heptafluoro-1-(2-pyrrolyl)-1-butanol | 159355-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,2,3,3,4,4,4-heptafluoro-1-(2-pyrrolyl)-1-butanol
• 英文别名: 2,2,3,3,4,4,4-heptafluoro-1-(1H-pyrrol-2-yl)butan-1-ol
• CAS: 159355-62-1
• 化学式: C₈H₆F₇NO
• 分子量: 265.131
• InChiKey: YYGDMWPVPDWMPY-UHFFFAOYSA-N

物化性质

• 沸点：
  247.6±40.0 °C(Predicted)
• 密度：
  1.558±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2,3,3,4,4,4-heptafluoro-1-(2-pyrrolyl)-1-butanol 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 3.08h， 生成
  参考文献：
  名称：

  On the Negligible Impact of Ruffling on the Electronic Spectra of Porphine, Tetramethylporphyrin, and Perfluoroalkylporphyrins

  摘要：

  In the first part of this paper, the syntheses, structural characterization, molecular modeling, and electronic spectra for planar and nonplanar perfluoroatkylated porphyrins, (R-f)(4)P's, are reported. These studies demonstrate that the intrinsic substituent effect of the perfluoroalkyl group on the long-wavelength electronic spectrum of porphyrins is substantial, and similar tin magnitude) to that of a phenyl ring, Moreover, it is shown that out-of-plane distortion of (R-f)(4)P'S has a negligible impact on their electronic spectra. These data bolster the findings of our earlier work and demonstrate that nonplanarity of (R-f)(4)P'S does not result in a red-shift in their optical spectra. In the second part of this paper, time-dependent density functional spectral calculations (B3LYP/6-311G*/TD) for porphine, 5,10,15,20-tetrakis(trifluoromethyl)porphrin and 5,10,15, 20-tetramethylporphyrin in a variety of ruffled conformations are reported. The results of these studies indicate that (1) substantial ruffling of porphyrins has a negligible effect upon their electronic spectra, (2) similarly small effects upon electronic spectra are predicted if electron-withdrawing or electron-releasing groups decorate the porphyrin periphery, (3) for sterically encumbered porphyrins, ruffling can actually result in hypsochromic shifts in various absorption bands, and (4) the bulk of the red-shift commonly thought to be due to nonplanar distortion actually arises from other substituent effects. These results pose serious challenges to previous theoretical and empirical studies that have sought to find a cause-and-effect relationship between nonplanarity and electronic spectra in porphyrins.

  DOI：

  10.1021/ja003137y
• 作为产物：
  描述：

  2-(perfluorobutyryl)pyrrole 在 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 2,2,3,3,4,4,4-heptafluoro-1-(2-pyrrolyl)-1-butanol
  参考文献：
  名称：

  Functionalized porphyrins from meso-poly-halogeno-alkyl-dipyrromethanes: synthesis and characterization

  摘要：

  简要概述 英文 法文 基于吡咯-亚醇衍生物，采用三种优化的实验条件合成了六种具有meso-多卤烷基链的双吡咯甲烷（DPM）。一方面，p-乙氧基苯铝醛与含有全氟烷基链（CF3、C3F7或C7F15）的DPM的缩合反应在氧化后以合理的产率生成了预期的trans-A2B2-卟啉。另一方面，从meso-(二氯甲基)双吡咯甲烷直接获得了5,15-二甲酰基-10,20-二芳基卟啉，而使用meso-(氯二氟甲基)双吡咯甲烷时则分离到了含有两个meso-酰氟基团的前所未见的卟啉的痕量产物。与以往报道的方法相比，双甲酰卟啉的直接形成具有竞争力，并已扩展到其他苯甲醛。通过结合光物理、 electrochemical、结构和理论研究，揭示了不同取代基对卟啉的电吸引特性。 补充材料： 本文的补充材料以单独文件形式提供： crchim-97-suppl.pdf

  DOI：

  10.5802/crchim.97

文献信息

• Synthesis, Spectra and Photophysics of some Free Base Tetrafluoroalkyl and Tetrafluoroaryl Porphyrins with Potential Applications in Imaging¶
  作者：J. C. P. Grancho、M. M. Pereira、M. da G. Miguel、A. M. Rocha Gonsalves、H. D. Burrows

  DOI：10.1562/0031-8655(2002)075<0249:ssapos>2.0.co;2

  日期：——

  Abstract The synthesis, characterization and photophysical properties of two perfluoroalkyl (5,10,15,20-tetrakis-[trifluoromethyl]- and [heptafluoropropyl]-porphyrin) and two perfluoroaryl (5,10,15,20-tetrakis-[2,6-difluorophenyl]- and [pentafluorophenyl]-porphyrin) are described, with reference to their potential in both photodynamic therapy (PDT) and in vivo imaging by fluorescence and 19F nuclear

  摘要 两种全氟烷基（5,10,15,20-四-[三氟甲基]-和[七氟丙基]-卟啉）和两种全氟芳基（5,10,15,20-四-[2,描述了 6-二氟苯基]-和 [五氟苯基]-卟啉），并参考了它们在光动力疗法 (PDT) 和荧光和 19F 核磁共振光谱的体内成像方面的潜力。报告了吸收和荧光光谱、荧光寿命和三重态-单重态差异光谱。三线态产率已通过闪光光解和脉冲辐解获得，而敏化单线态氧形成的产率已通过时间分辨磷光度法确定。所有四种化合物都显示出高产率的三线态形成和单线态氧敏化。光谱特性，
• Synthesis, Structure, Electronic Spectroscopy, Photophysics, Electrochemistry, and X-ray Photoelectron Spectroscopy of Highly-Electron-Deficient [5,10,15,20-Tetrakis(perfluoroalkyl)porphinato]zinc(II) Complexes and Their Free Base Derivatives
  作者：James G. Goll、Kevin T. Moore、Abhik Ghosh、Michael J. Therien

  DOI：10.1021/ja9610904

  日期：1996.1.1

  The synthesis, optical spectroscopy, photophysical properties, electrochemistry, and X-ray photoelectron spectroscopy of a series of [5,10,15,20-tetrakis(perfluoroalkyl)porphinato]zinc(II) complexes and their free base analogs are reported. The title compounds were prepared by a condensation methodology that utilizes perfluoro-1-(2‘-pyrrolyl)-1-alkanol precursors and employs continuous water removal

  报道了一系列 [5,10,15,20-四(全氟烷基)卟吩基]锌 (II) 配合物及其游离碱类似物的合成、光谱、光物理特性、电化学和 X 射线光电子能谱。标题化合物是通过缩合方法制备的，该方法使用全氟-1-(2'-吡咯基)-1-烷醇前体，并在整个反应过程中连续去除水以产生内消旋全氟化碳取代的卟啉。卟啉悬垂的内消旋全氟烷基的性质对大环的溶解度特性有相当大的影响。[5,10,15,20-四(七氟丙基)卟吩基]锌(II)的单吡啶基加合物的结构具有S4-扭曲的卟啉核；X射线数据如下：P1，a=15.1330(5)A，b=19.2780(6)A，
• Porphyrins and porphyrin synthesis techniques
  申请人：Trustees of the University of Pennsylvania

  公开号：US05955603A1

  公开（公告）日：1999-09-21

  Strapped porphyrins and electron-deficient porphyrins are provided, as well as processes and intermediates for their preparation. In certain embodiments, such compounds are prepared by nucleophilic displacement of leaving groups from methylpyrroles. In other embodiments, such compounds are prepared by condensing pyrrole derivatives and removing water thus formed from the resulting reaction mixture.

  本发明提供了带有束缚卟啉和电子不足卟啉，以及它们的制备方法和中间体。在某些实施例中，这些化合物通过从甲基吡咯中亲核取代离去基团来制备。在其他实施例中，这些化合物通过缩合吡咯衍生物并从生成的反应混合物中去除水来制备。
• Pyrrolic compounds
  申请人：Trustees of the University of Pennsylvania

  公开号：US05817830A1

  公开（公告）日：1998-10-06

  Novel methylpyrroles are provided, as well as processes for their preparation.

  提供了新型甲基吡咯，并提供了它们的制备过程。
• Electron-deficient porphyrins and processes and intermediates for
  申请人：Trustees of The University of Pennsylvania

  公开号：US05599924A1

  公开（公告）日：1997-02-04

  Electron-deficient porphyrins are provided, as well as processes and intermediates for their preparation. In preferred embodiments, the electron-deficient porphyrins are prepared by condensing pyrrole derivatives and removing water thus formed from the resulting reaction mixture.

  提供了电子不足的卟啉，以及它们的制备过程和中间体。在优选实施例中，电子不足的卟啉是通过缩合吡咯衍生物并从所得到的反应混合物中去除形成的水来制备的。