phenylacetic acid | 100074-40-6

• 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: phenylacetic acid
• 英文别名: (2-ethoxy-2-oxoethyl) 2-(4-methylphenyl)acetate
• CAS: 100074-40-6
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: COFFWJCTUFAXDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  335.1±22.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  phenylacetic acid 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 5.5h， 生成 2-[(3-fluoro-4-morpholin-4-ylphenyl)-hydroxymethyl]-3-methoxy-4-(4-methylphenyl)-2H-furan-5-one
  参考文献：
  名称：

  普尔维酮及其衍生物的简便合成，抗菌活性

  摘要：

  从五个共同的前体苯乙酸中分五步合成了普尔维酮和几种3-氟-4-吗啉代取代的普尔维酮衍生物。大多数合成吗啉取代的聚乙烯醇对大肠杆菌均具有抑制作用。首次报道了普尔维酮及其衍生物对革兰氏阴性菌的抑制作用。

  DOI：

  10.1016/j.bmcl.2012.11.090
• 作为产物：
  描述：

  对甲基苯乙酸 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 phenylacetic acid
  参考文献：
  名称：

  Novel 3-arylfuran-2(5H)-one-fluoroquinolone hybrid: Design, synthesis and evaluation as antibacterial agent

  摘要：

  3-Arylfuran-2(5H)-one, a novel antibacterial pharmacophore targeting tyrosyl-tRNA synthetase (TyrRS), was hybridized with the clinically used fluoroquinolones to give a series of novel multi-target antimicrobial agents. Thus, twenty seven 3-arylfuran-2(5H)-one-fluoroquinolone hybrids were synthesized and evaluated for their antimicrobial activities. Some of the hybrids exhibited merits from both parents, displaying a broad spectrum of activity against resistant strains including both Gram-negative and Gram-positive bacteria. The most potent compound (11) in antibacterial assay shows MIC50 of 0.11μg/mL against Multiple drug resistant Escherichia coli, being about 51-fold more potent than ciprofloxacin. The enzyme assays reveal that 11 is a potent multi-target inhibitor with IC50 of 1.15±0.07μM against DNA gyrase and 0.12±0.04μM against TyrRS, respectively. Its excellent inhibitory activities against isolated enzymes and intact cells strongly suggest that 11 deserves to further research as a novel antibiotic.

  DOI：

  10.1016/j.bmc.2014.05.018

文献信息

• Synthesis of (E)- and (Z)-pulvinones
  作者：Alexander C. Campbell、Maurice S. Maidment、John H. Pick、Donald F. M. Stevenson

  DOI：10.1039/p19850001567

  日期：——

  one of which involves a novel Wittig reaction. For the first time, members of the E-series, including the parent (E)-pulvinone, are reported and the structural elucidation of the geometric isomers is described. A method for quantitatively converting (E)-pulvinones into (Z)-pulvinones is presented, together with a technique for differentiating between the isomers.

  已经开发出两种新的途径获得pulvinones，其中一种涉及新颖的Wittig反应。首次报道了E系列的成员，包括母体（E）-普尔维酮，并描述了几何异构体的结构。提出了一种将（E）-普尔维酮定量转化为（Z）-普尔维酮的方法，以及区分异构体的技术。
• 一种化合物以及制备方法和应用
  申请人：郑州大学

  公开号：CN110872263B

  公开（公告）日：2021-09-28

  本申请公开了一种化合物，其结构式如下式所示：其中，R1选自F、Cl、Br、C1～C5的烷基、具有式(1)所示结构式的基团中的任意一种；n＝0、1、2、3、4或5；R2选自具有式(1)所示结构式的基团、具有式(2)所示结构式的基团、具有式(3)所示结构式的基团中的任意一种。所述化合物制备方法简单，可作为神经氨酸酶抑制剂，具有良好的抗病毒活性。
• Synthesis, molecular docking and biological evaluation of 3-arylfuran-2(5H)-ones as anti-gastric ulcer agent
  作者：Xu-Dong Wang、Wei Wei、Peng-Fei Wang、Li-Cheng Yi、Wei-Kang Shi、Yong-Xiang Xie、Lang-Zhou Wu、Nian Tang、Liang-Song Zhu、Jia Peng、Chan Liu、Xian-Hui Li、Shi Tang、Zhu-Ping Xiao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2015.05.026

  日期：2015.8

  3-Arylfuran-2(5H)-one derivatives show good antibacterial activity and were determined as tyrosyl-tRNA synthetase (TyrRS) inhibitors. In a systematic medicinal chemistry exploration, we demonstrated chemical opportunities to treat infections caused by Helicobacter pylori. Twenty 3-arylfuran-2(5H)-ones were synthesized and evaluated for anti-H. pylori, antioxidant and anti-urease activities which are closely interconnected with H. pylori infection. The results displayed that some of the compounds show excellent antioxidant activity, and good anti-H. pylori and urease inhibitory activities. Out of these compounds, 3( 3-methylphenyl) furan-2(5H)-one (b9) showed the most potent antioxidant activity (IC50 = 8.2 mu M) and good anti-H. pylori activity (MIC50 = 2.6 mu g/mL), and it can be used as a good candidate for discovering novel anti-gastric ulcer agent. (C) 2015 Elsevier Ltd. All rights reserved.