ethyl (2Z)-3-hydroxy-3-(2,3,4,5-tetrafluorophenyl)-propyl-2-enoate | 1361000-74-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (2Z)-3-hydroxy-3-(2,3,4,5-tetrafluorophenyl)-propyl-2-enoate
• 英文别名: ethyl (2Z)-3-hydroxy-3-(2,3,4,5-tetrafluorophenyl)prop-2-enoate；ethyl (Z)-3-hydroxy-3-(2,3,4,5-tetrafluorophenyl)prop-2-enoate
• CAS: 1361000-74-9
• 化学式: C₁₁H₈F₄O₃
• 分子量: 264.176
• InChiKey: SUHJYTWDWWAHOF-DAXSKMNVSA-N

物化性质

• 沸点：
  312.5±42.0 °C(Predicted)
• 密度：
  1.430±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  diethyl (2,3,4,5-tetrafluorobenzoyl)malonate 在 水 作用下， 反应 5.0h， 以98%的产率得到ethyl (2Z)-3-hydroxy-3-(2,3,4,5-tetrafluorophenyl)-propyl-2-enoate
  参考文献：
  名称：

  Catalyst-free transformations of diethyl 2-ethoxymethylenemalonate and diethyl polyfluorobenzoylmalonates in water

  摘要：

  The unusual transformation of diethyl 2-ethoxymethylenemalonate into triethyl 1,3,5-benzenetricarboxylate is described. This one-pot reaction proceeds in water without any catalyst in a good yield. One of the proposed intermediates of this process is also used under similar conditions to give the desired trisubstituted benzene. A catalyst-free, efficient, practical, and convenient process in water based on deethoxycarbonylation has been developed to form ethyl polyfluorobenzoylacetates in a high yield from diethyl polyfluorobenzoylmalonates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.015

文献信息

• Features of synthesis and structure of ethyl (2Z)-3-hydroxy-(2,3,4,5-tetrafluorophenyl)-propyl-2-enoate
  作者：D. N. Bazhin、E. V. Shchegol’kov、Yu. S. Kudyakova、K. V. Scherbakov、Ya. V. Burgart、V. I. Saloutin

  DOI：10.1134/s1070363212010197

  日期：2012.1

  The structure of key intermediates in the synthesis of fluoroquinolone antibiotics: diethyl (2,3,4,5-tetrafluorobenzoyl)malonate and ethyl (2Z)-3-hydroxy-(2,3,4,5-tetrafluorophenyl)prop-2-enoate was for first time studied using X-ray diffraction (XRD) and H-1, F-19 NMR spectroscopy. In solution both the esters were shown to exist as a mixture of enol and ketone tautomeric forms with predominance of the latter. According to the XRD analysis, ethyl (2Z)-3-hydroxy-(2,3,4,5-tetrafluorophenyl)prop-2-enoate in the solid state exists entirely in the enol form.