(Z)-ethyl 2-fluoro-3-(3,4,5-trimethoxyphenyl)acrylate | 1158176-45-4

• 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: (Z)-ethyl 2-fluoro-3-(3,4,5-trimethoxyphenyl)acrylate
• 英文别名: ethyl (Z)-2-fluoro-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
• CAS: 1158176-45-4
• 化学式: C₁₄H₁₇FO₅
• 分子量: 284.284
• InChiKey: OZSMVLITSWZSOG-POHAHGRESA-N

物化性质

• 沸点：
  387.0±42.0 °C(predicted)
• 密度：
  1.164±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二溴氟乙酸乙酯 、 3,4,5-三甲氧基苯甲醛 在 diethylzinc 、 氯化铵 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (Z)-ethyl 2-fluoro-3-(3,4,5-trimethoxyphenyl)acrylate 、 (2RS,3SR)-ethyl 2-bromo-2-fluoro-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propanoate 、 (2SR,3SR)-ethyl 2-bromo-2-fluoro-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propanoate
  参考文献：
  名称：

  Diethylzinc-Mediated One-Step Stereoselective Synthesis of α-Fluoroacrylates from Aldehydes and Ketones. Two Different Pathways Depending on the Carbonyl Partner

  摘要：

  A efficient methodology allowing the one-pot stereoselective synthesis of alpha-fluoroacrylates, based on the addition of ethyl dibromofluoroacetate to a carbonyl derivative using diethylzinc as organometallic mediator, is described. Two different pathways have been identified depending on the involved carbonyl partner. In the case of aldehydes, an E2-type mechanism has been identified, whereas ketones go through an E1cb-type mechanism.

  DOI：

  10.1021/jo900422m

文献信息

• Diethylzinc-Mediated One-Step Stereoselective Synthesis of α-Fluoroacrylates from Aldehydes and Ketones. Two Different Pathways Depending on the Carbonyl Partner
  作者：G. Lemonnier、L. Zoute、G. Dupas、J.-C. Quirion、P. Jubault

  DOI：10.1021/jo900422m

  日期：2009.6.5

  A efficient methodology allowing the one-pot stereoselective synthesis of alpha-fluoroacrylates, based on the addition of ethyl dibromofluoroacetate to a carbonyl derivative using diethylzinc as organometallic mediator, is described. Two different pathways have been identified depending on the involved carbonyl partner. In the case of aldehydes, an E2-type mechanism has been identified, whereas ketones go through an E1cb-type mechanism.