(E)-3-(2-(苄氧基)-4-((2-甲氧基乙氧基)甲氧基)苯基)丙烯酸乙酯 | 1016896-51-7

• 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
• 中文名称: (E)-3-(2-(苄氧基)-4-((2-甲氧基乙氧基)甲氧基)苯基)丙烯酸乙酯
• 英文名称: Ethyl (E)-3-(2-(benzyloxy)-4-((2-methoxyethoxy)methoxy)phenyl)acrylate
• 英文别名: ethyl (E)-3-[4-(2-methoxyethoxymethoxy)-2-phenylmethoxyphenyl]prop-2-enoate
• CAS: 1016896-51-7
• 化学式: C₂₂H₂₆O₆
• 分子量: 386.445
• InChiKey: WVLZXTTVANQRPO-ZRDIBKRKSA-N

物化性质

• 沸点：
  527.6±50.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  28.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  氨基甲酸苄酯 、 (E)-3-(2-(苄氧基)-4-((2-甲氧基乙氧基)甲氧基)苯基)丙烯酸乙酯 在 sodium hydroxide 、 次氯酸叔丁酯 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 、 potassium osmate(VI) 作用下， 以 丙醇 为溶剂， 反应 3.08h， 以64%的产率得到ethyl (2R,3S)-3-(2-(benzyloxy)-4-((2-methoxyethoxy)methoxy)phenyl)-3-(((benzyloxy)carbonyl)amino)-2-hydroxypropanoate
  参考文献：
  名称：

  Benzofuran-Derived Cyclic β-Amino Acid Scaffold for Building a Diverse Set of Flavonoid-Like Probes and the Discovery of a Cell Motility Inhibitor

  摘要：

  We report here a practical, enantioselective synthesis of benzofuran-derived, cyclic trans-beta-amino acid scaffold. In two cases, tricyclic derivatives having six- and eight-membered unsaturated lactams were obtained from this versatile scaffold. To explore the biological applications, these compounds were subjected to cell-based assays, using NIH3T3 mouse cells to examine their potency as cell motility inhibitors and identified 18 as a potent cell motility inhibitor (IC(50) approximate to 40 mu M in chamber cell migration assay).

  DOI：

  10.1021/ol800050g
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.58h， 以95%的产率得到(E)-3-(2-(苄氧基)-4-((2-甲氧基乙氧基)甲氧基)苯基)丙烯酸乙酯
  参考文献：
  名称：

  Benzofuran-Derived Cyclic β-Amino Acid Scaffold for Building a Diverse Set of Flavonoid-Like Probes and the Discovery of a Cell Motility Inhibitor

  摘要：

  We report here a practical, enantioselective synthesis of benzofuran-derived, cyclic trans-beta-amino acid scaffold. In two cases, tricyclic derivatives having six- and eight-membered unsaturated lactams were obtained from this versatile scaffold. To explore the biological applications, these compounds were subjected to cell-based assays, using NIH3T3 mouse cells to examine their potency as cell motility inhibitors and identified 18 as a potent cell motility inhibitor (IC(50) approximate to 40 mu M in chamber cell migration assay).

  DOI：

  10.1021/ol800050g