(2-Ethoxy-2-oxoethyl) 2-(3-methoxyphenyl)acetate | 100074-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2-Ethoxy-2-oxoethyl) 2-(3-methoxyphenyl)acetate
• 英文别名: (2-ethoxy-2-oxoethyl) 2-(3-methoxyphenyl)acetate
• CAS: 100074-35-9
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: ZZQYILFGIYAHHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-Ethoxy-2-oxoethyl) 2-(3-methoxyphenyl)acetate 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 3-(2-bromoethoxy)-4-(3-methoxyphenyl)-2H-furan-5-one
  参考文献：
  名称：

  4-Alkoxy-3-arylfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase: Synthesis, molecular docking and antibacterial evaluation

  摘要：

  A series of novel 4-alkoxy-3-arylfuran-2(5H)-ones as tyrosyl-tRNA synthetase inhibitors were synthesized. Of these compounds, 3-(4-hydroxyphenyl)-4-(2-morpholinoethoxy)furan-2(5H)-one (27) was the most potent. The binding model and structure-activity relationship indicate that replacement of morpholine-ring in the side chain of 27 with a substituent containing more hydrophilic groups would be more suitable for further modification. Antibacterial assay revealed that the synthetic compounds are effective against growth of Gram-positive organisms, and 27 is the most potent agent against Staphylococcus ;aureus ATCC 25923 with MIC50 value of 0.23 mu g/mL. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.042
• 作为产物：
  描述：

  3-甲氧基苯乙酸 、 溴乙酸乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (2-Ethoxy-2-oxoethyl) 2-(3-methoxyphenyl)acetate
  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

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。
• 4-Alkoxy-3-arylfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase: Synthesis, molecular docking and antibacterial evaluation
  作者：Zhu-Ping Xiao、Hui Ouyang、Xu-Dong Wang、Peng-Cheng Lv、Ze-Jun Huang、She-Rong Yu、Tian-Fang Yi、Ye-Ling Yang、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.05.042

  日期：2011.7

  A series of novel 4-alkoxy-3-arylfuran-2(5H)-ones as tyrosyl-tRNA synthetase inhibitors were synthesized. Of these compounds, 3-(4-hydroxyphenyl)-4-(2-morpholinoethoxy)furan-2(5H)-one (27) was the most potent. The binding model and structure-activity relationship indicate that replacement of morpholine-ring in the side chain of 27 with a substituent containing more hydrophilic groups would be more suitable for further modification. Antibacterial assay revealed that the synthetic compounds are effective against growth of Gram-positive organisms, and 27 is the most potent agent against Staphylococcus ;aureus ATCC 25923 with MIC50 value of 0.23 mu g/mL. (C) 2011 Elsevier Ltd. All rights reserved.