(苯基乙酰氧基) 乙酸乙酯 | 91497-39-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (苯基乙酰氧基) 乙酸乙酯
• 中文别名: (苯基乙酰氧基)乙酸乙酯
• 英文名称: ethoxycarbonylmethyl phenylacetate
• 英文别名: Ethyl (phenylacetoxy)acetate；(2-ethoxy-2-oxoethyl) 2-phenylacetate
• CAS: 91497-39-1
• 化学式: C₁₂H₁₄O₄
• mdl: MFCD00012216
• 分子量: 222.241
• InChiKey: UJHKDJROFCQOBO-UHFFFAOYSA-N

物化性质

• 沸点：
  120 °C(Press: 0.05 Torr)
• 密度：
  1.121 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 稳定性/保质期：
  在常温常压下稳定，应避免接触强氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 海关编码：
  2916399090
• 储存条件：
  保持贮藏器密封，并将其放入一个紧密封装的容器中。储存在阴凉、干燥的地方。

反应信息

• 作为反应物：
  描述：

  (苯基乙酰氧基) 乙酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 、 丙酮 、 叔丁醇 为溶剂， 反应 4.0h， 生成 5-bromo-4-methoxy-3-phenylfuran-2(5H)-one
  参考文献：
  名称：

  （E）-和（Z）-pulvinones的合成

  摘要：

  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。

  DOI：

  10.1039/p19850001567
• 作为产物：
  描述：

  苯乙酸 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 (苯基乙酰氧基) 乙酸乙酯
  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

• A facile synthesis, antibacterial activity of pulvinone and its derivatives
  作者：Hai-Wei Xu、Chao Xu、Zi-qi Fan、Ling-Jie Zhao、Hong-Min Liu

  DOI：10.1016/j.bmcl.2012.11.090

  日期：2013.2

  Pulvinone and several 3-fluoro-4-morpholino substituted pulvinone derivatives were synthesized in five steps from a common precursor, phenyl acetic acid. Most of synthetic morpholine substituted pulvinones showed inhibitory activity against Esherichia coli. For the first time, the inhibition of pulvinone and its derivatives against Gram-negative bacteria was reported.

  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。
• Silver-Catalyzed Functionalization of Esters by Carbene Transfer: The Role of Ylide Zwitterionic Intermediates
  作者：Riccardo Gava、M. Ángeles Fuentes、Maria Besora、Tomás R. Belderrain、Kane Jacob、Feliu Maseras、Michel Etienne、Ana Caballero、Pedro J. Pérez

  DOI：10.1002/cctc.201402241

  日期：2014.8

  The reaction of esters with ethyl diazoacetate catalyzed by the complex [F27–TpAg(acetone)] generates α‐(acyloxy)acetates in moderate to high yields. This is a novel transformation in the context of carbene‐transfer reactions from diazo compounds that, according to experimental and theoretical data, is suggested to occur through zwitterionic intermediates.

  络合物[F 27 -Tp Ag（丙酮）]催化的酯类与重氮乙酸乙酯反应生成α-（酰氧基）乙酸酯，产率中等至高。在重氮化合物进行卡宾转移反应的背景下，这是一种新颖的转变，根据实验和理论数据，该转变建议通过两性离子中间体发生。
• Nonmetal Catalyzed Insertion Reactions of Diazocarbonyls to Acid Derivatives in Fluorinated Alcohols
  作者：Lidia Dumitrescu、Kaouther Azzouzi-Zriba、Danièle Bonnet-Delpon、Benoit Crousse

  DOI：10.1021/ol102923h

  日期：2011.2.18

  The insertion reaction of diazocarbonyls to acids could be performed smoothly in fluorinated alcohols in the absence of metal catalyst. This new procedure allowed the chemoselective preparation of various functionalized compounds such as acyloxyesters, depsipeptides, and sulfonate, phosphonate, or boronate derivatives.

  在不存在金属催化剂的情况下，重氮羰基化合物向酸的插入反应可以在氟化醇中顺利进行。该新方法允许化学选择性地制备各种官能化的化合物，例如酰氧基酯，二肽，以及磺酸盐，膦酸盐或硼酸盐衍生物。
• [EN] PROCESS FOR MAKING PHENYL HETEROCYCLES USEFUL AS COX-2 INHIBITORS<br/>[FR] PROCEDE DE PRODUCTION D'HETEROCYCLES PHENYLIQUES UTILES COMME INHIBITEURS DE COX-2
  申请人：MERCK & CO., INC.

  公开号：WO1996008482A1

  公开（公告）日：1996-03-21

  (EN) The invention encompasses a process for making compounds of formula (I) useful in the treatment of cyclooxygenase-2 mediated diseases.(FR) Procédé de production de composés de formule (I) utiles dans le traitement de maladies cyclooxygénase-2-dépendantes.

  该发明涉及一种用于制备式(I)化合物的方法，该化合物可用于治疗环氧化酶-2介导的疾病。
• Synthesis, structure, molecular docking, and structure–activity relationship analysis of enamines: 3-Aryl-4-alkylaminofuran-2(5H)-ones as potential antibacterials
  作者：Zhu-Ping Xiao、Xing-Bing He、Zhi-Yun Peng、Tao-Ju Xiong、Juan Peng、Li-Hua Chen、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.01.051

  日期：2011.3

  Thirty-one 3-aryl-4-alkylaminofuran-2(5H)-ones were designed, prepared and tested for their antibacterial activity. Some of them showed significant antibacterial activity against Gram-positive organisms, especially against Staphylococcus aureus ATCC 25923, but all were inactive against Gram-negative organisms. Out of these compounds, 3-(4-bromophenyl)-4-(2-(4-nitrophenyl)hydrazinyl)furan-2(5H)-one (4a11) showed the most potent antibacterial activity against S. aureus ATCC 25923 with MIC50 of 0.42 mu g/mL. The enzyme assay revealed that the possible antibacterial mechanism of the synthetic compounds might be due to their inhibitory activity against tyrosyl-tRNA synthetase. Molecular dockings of 4a11 into S. aureus tyrosyl-tRNA synthetase active site were also performed. This inhibitor snugly fitting the active site might well explain its excellent inhibitory activity. Meanwhile, this modeling disclosed that a more suitable optimization strategy might be to modify the benzene ring at 3-position of furanone with hydrophilic groups. (C) 2011 Elsevier Ltd. All rights reserved.