3-(dimethylamino)-2-(4-fluorophenyl)acrylic acid | 773098-72-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(dimethylamino)-2-(4-fluorophenyl)acrylic acid
• 英文别名: 3-(dimethylamino)-2-(4-fluorophenyl)prop-2-enoic acid
• CAS: 773098-72-9
• 化学式: C₁₁H₁₂FNO₂
• 分子量: 209.22
• InChiKey: ZTEOUXDHANJWBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(dimethylamino)-2-(4-fluorophenyl)acrylic acid 在 水 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 生成 3-dimethylamino-2-(4-fluorophenyl)propenal
  参考文献：
  名称：

  Lactim–lactam tautomerism is favoured over enol–keto tautomerism in 2-hydroxy-5-(4-fluorophenyl)nicotinic acid: Experimental and quantum chemical approach

  摘要：

  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.

  DOI：

  10.1016/j.jphotochem.2010.06.028
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 4-氟苯乙酸 在 三氯氧磷 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 7.0h， 生成 3-(dimethylamino)-2-(4-fluorophenyl)acrylic acid
  参考文献：
  名称：

  Design, Synthesis, and Activity of a Series of Arylpyrid-3-ylmethanones as Type I Positive Allosteric Modulators of α7 Nicotinic Acetylcholine Receptors

  摘要：

  A series of novel arylpyrid-3-ylmethanones (7a-aa) were designed as modulators of alpha 7 nicotinic acetylcholine receptors (nAChRs). The methanones were found to be type I positive allosteric modulators (PAMs) of human alpha 7 nAChRs expressed in Xenopus ooctyes. Structure-activity relationship (SAR) studies resulted in the identification of compound 7v as a potent and efficacious type I PAM with maximum modulation of a nicotine EC5 response of 1200% and EC50 = 0.18 mu M. Compound 7z was active in reversing the effect of scopolamine in the novel object recognition (NOR) paradigm with a minimum effective ip dose of 1.0 mg/kg (2.7 mu mol/kg). This effect was blocked by the selective alpha 7 nAChR antagonist methyllycaconitine (MLA). These compounds are nAChRs that may have therapeutic value in restoring impaired sensory Alzheimer's disease. potent type I positive allosteric modulators of alpha 7 gating and cognitive deficits in schizophrenia and Alzheimer's disease.

  DOI：

  10.1021/jm400704g