benzyl 3-((E)-2-ethoxycarbonylvinyl)benzoate | 874204-69-0

• 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: benzyl 3-((E)-2-ethoxycarbonylvinyl)benzoate
• 英文别名: Phenylmethyl 3-[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]benzoate；benzyl 3-[(E)-3-ethoxy-3-oxoprop-1-enyl]benzoate
• CAS: 874204-69-0
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: VPPWTIGCCLYNLN-VAWYXSNFSA-N

物化性质

• 沸点：
  463.9±33.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  benzyl 3-((E)-2-ethoxycarbonylvinyl)benzoate 在 palladium on activated charcoal 草酰氯 、 氢气 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 ethyl 3-[3-(4-isobutoxybenzoyl)phenyl]propionate
  参考文献：
  名称：

  Discovery of Nonpeptidic Small-Molecule AP-1 Inhibitors:  Lead Hopping Based on a Three-Dimensional Pharmacophore Model

  摘要：

  We designed and synthesized small-molecule activator protein-1 (AP-1) inhibitors based on a three-dimensional (3D) pharmacophore model that we had previously derived from a cyclic decapeptide exhibiting AP-1 inhibitory activity. New AP-1 inhibitors with a 1-thia-4-azaspiro[4.5]decane or a benzophenone scaffold, which inhibit the DNA-binding and transactivation activities of AP-1, were discovered using a "lead hopping" procedure. An additional investigation of the benzophenone analogues confirmed the reliability of the pharmacophore model, its utility to discover AP-1 inhibitors, and the potency of the benzophenone derivatives as a lead series.

  DOI：

  10.1021/jm050550d
• 作为产物：
  描述：

  benzyl 3-formylbenzoate 、 磷酰基乙酸三乙酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以94%的产率得到benzyl 3-((E)-2-ethoxycarbonylvinyl)benzoate
  参考文献：
  名称：

  Discovery of Nonpeptidic Small-Molecule AP-1 Inhibitors:  Lead Hopping Based on a Three-Dimensional Pharmacophore Model

  摘要：

  We designed and synthesized small-molecule activator protein-1 (AP-1) inhibitors based on a three-dimensional (3D) pharmacophore model that we had previously derived from a cyclic decapeptide exhibiting AP-1 inhibitory activity. New AP-1 inhibitors with a 1-thia-4-azaspiro[4.5]decane or a benzophenone scaffold, which inhibit the DNA-binding and transactivation activities of AP-1, were discovered using a "lead hopping" procedure. An additional investigation of the benzophenone analogues confirmed the reliability of the pharmacophore model, its utility to discover AP-1 inhibitors, and the potency of the benzophenone derivatives as a lead series.

  DOI：

  10.1021/jm050550d