2-hydroxy-5-(4-fluorophenyl)nicotinic acid | 31695-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-hydroxy-5-(4-fluorophenyl)nicotinic acid
• 英文别名: HFPNA；5-(4-fluorophenyl)-2-oxo-1H-pyridine-3-carboxylic acid
• CAS: 31695-66-6
• 化学式: C₁₂H₈FNO₃
• 分子量: 233.199
• InChiKey: CSPFUMHTRJPURT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-5-(4-fluorophenyl)nicotinic acid 在 喹啉 作用下， 反应 14.0h， 生成 5-(4-氟苯基)-1H-吡啶-2-酮
  参考文献：
  名称：

  Excited State Lactim to Lactam Type Tautomerization Reaction in 5-(4-Fluorophenyl)-2-Hydroxypyridine: Spectroscopic Study and Quantum Chemical Calculation

  摘要：

  通过稳态和时间分辨光谱以及量子化学计算，研究了 5-(4-氟苯基)-2-羟基吡啶 (FP2HP) 的光物理特性。由于稳定性差异较小，FP2HP 分子在基态以内酰胺和内酰胺形式存在，但由于高势垒能，不会发生内酰胺到内酰胺的异构化。而在激发态，内酰胺形式发生了同分异构，产生了内酰胺同分异构体的红移发射以及内酰胺形式的局部发射。在极性原溶剂中，内酰胺-内酰胺同分异构体的屏障迅速降低，只形成内酰胺同分异构体。温度对激发态的同分异构平衡有明显的影响，并清楚地反映在测得的平衡常数（K tau 0）和自由能变化（ΔG0）中。报告了在 Hartree Fock 和密度泛函理论水平上对 FP2HP 同分异构体平衡进行的结构计算、利用极化连续模型计算的异构体在不同溶剂中的稳定性，以及基态和激发态沿质子转移坐标的理论势能面。

  DOI：

  10.1007/s10895-010-0692-3
• 作为产物：
  描述：

  2-hydroxy-5-(4-fluorophenyl)nicotinonitrile 在 盐酸 、 溶剂黄146 作用下， 反应 18.0h， 生成 2-hydroxy-5-(4-fluorophenyl)nicotinic acid
  参考文献：
  名称：

  Excited State Lactim to Lactam Type Tautomerization Reaction in 5-(4-Fluorophenyl)-2-Hydroxypyridine: Spectroscopic Study and Quantum Chemical Calculation

  摘要：

  通过稳态和时间分辨光谱以及量子化学计算，研究了 5-(4-氟苯基)-2-羟基吡啶 (FP2HP) 的光物理特性。由于稳定性差异较小，FP2HP 分子在基态以内酰胺和内酰胺形式存在，但由于高势垒能，不会发生内酰胺到内酰胺的异构化。而在激发态，内酰胺形式发生了同分异构，产生了内酰胺同分异构体的红移发射以及内酰胺形式的局部发射。在极性原溶剂中，内酰胺-内酰胺同分异构体的屏障迅速降低，只形成内酰胺同分异构体。温度对激发态的同分异构平衡有明显的影响，并清楚地反映在测得的平衡常数（K tau 0）和自由能变化（ΔG0）中。报告了在 Hartree Fock 和密度泛函理论水平上对 FP2HP 同分异构体平衡进行的结构计算、利用极化连续模型计算的异构体在不同溶剂中的稳定性，以及基态和激发态沿质子转移坐标的理论势能面。

  DOI：

  10.1007/s10895-010-0692-3

文献信息

• New Synthetic Routes to 3-, 5-, and 6-Aryl-2-chloropyridines
  作者：Robert Church、Ronald Trust、J. Donald Albright、Dennis Powell

  DOI：10.1021/jo00117a029

  日期：1995.6

  The efficient synthesis of 3-, 5-, and 6-aryl-2-chloropyridines via the facile preparation of 5-(dimethyamino)aryl-substituted pentadienyl nitriles and cyclization with hydro chloric acid is described. This approach allows for the introduction of other electron-withdrawing substituents on the pyridine ring as well as the preparation of the desired unsubstituted arylpyridines. Some differences in the rates of cyclization of the pentadienyl nitriles as well as the yields of chloropyridines were observed that depended on the position and degree of substitution in the aryl substituent. The arylpentadienyl nitriles 5 and 6 could also be converted directly into the corresponding 2-aminopyridines.
• Lactim–lactam tautomerism is favoured over enol–keto tautomerism in 2-hydroxy-5-(4-fluorophenyl)nicotinic acid: Experimental and quantum chemical approach
  作者：Bijan Kumar Paul、Anuva Samanta、Samiran Kar、Nikhil Guchhait

  DOI：10.1016/j.jphotochem.2010.06.028

  日期：2010.8

  A model compound, 2-hydroxy-5-(4-fluorophenyl)nicotinic acid (HFPNA) has been synthesized and its ground and excited-state properties towards tautomerisation via possible two ways of proton transfer process have been elaborately examined by means of steady-state absorption, emission and time-resolved emission spectroscopy and quantum chemical calculations. The theme issue of the present contribution is to illustrate a direct competition between two potential excited-state intramolecular proton transfer (ESIPT) pathways within the same molecule. By a direct comparison of spectral characteristics of HFPNA with those of salicylic acid (SA) and 2-hydroxypyridine (2HP) under similar experimental conditions it has been demonstrated that lactim-lactam tautomerisation dominates over enol-keto tautomerisation in HFPNA. Experimental evidences and structural calculation at Density Functional Theory (DFT) (B3LYP/6-31G**) and Hartree-Fock (6-31G**) levels predict the existence of both lactim and lactam-forms in the ground state. The ground and excited-state theoretical potential energy surfaces (PES) of HFPNA along both the ways of proton transfer coordinate at DFT level reveal that PES of HFPNA resemble well with that of 2HP while there are prominent differences from that of SA. We also report on the possibility of application of the studied molecule as a sensor of medium-pH following its sensitive response towards pH of the medium. (C) 2010 Elsevier B.V. All rights reserved.
• Substituted 3-alkyl-6-phenyl-1,2,4-triazolo(4,3-a)pyridines, processes for their preparation and pharmaceutical compositions containing them
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0017438B1

  公开（公告）日：1983-03-02
• US4209626A
  申请人：——

  公开号：US4209626A

  公开（公告）日：1980-06-24
• US4244953A
  申请人：——

  公开号：US4244953A

  公开（公告）日：1981-01-13