methyl ( E)-4-[2-(5,8-(diphenyl)naphthalen)-2-yl-ethenyl]benzoate | 1582776-59-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: methyl ( E)-4-[2-(5,8-(diphenyl)naphthalen)-2-yl-ethenyl]benzoate
• CAS: 1582776-59-7
• 化学式: C₃₂H₂₄O₂
• 分子量: 440.541
• InChiKey: PJUHFGXGZPLYJK-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.13
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl ( E)-4-[2-(5,8-(diphenyl)naphthalen)-2-yl-ethenyl]benzoate 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以89%的产率得到(E)-4-[(5,8-(diphenyl)naphthalene-2-yl)ethenyl]benzoic acid
  参考文献：
  名称：

  Dual RXR Agonists and RAR Antagonists Based on the Stilbene Retinoid Scaffold

  摘要：

  Arotinoids containing a C5,C8-diphenylnaphthalene-2-y1 ring linked to a (C3-halogenated) benzoic acid via an ethenyl connector (but not the corresponding naphthamides), which are prepared by Horner-Wadsworth-Emmons reaction of naphthaldehydes and benzylphosphonates, display the rather unusual property of being RXR agonists (15-fold induction of the RXR reporter cell line was achieved at 3- to 10-fold lower concentration than 9-cis-retinoic acid) and RAR antagonists as shown by transient transactivation studies. The binding of such bulky ligands suggests that the RXR ligand-binding domain is endowed with some degree of structural elasticity.

  DOI：

  10.1021/ml400521f
• 作为产物：
  描述：

  methyl 5,8-diiodo-2-naphthoate 在 N,N-二甲基丙烯基脲 、 manganese(IV) oxide 、 正丁基锂 、 二异丁基氢化铝 、 sodium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 19.5h， 生成 methyl ( E)-4-[2-(5,8-(diphenyl)naphthalen)-2-yl-ethenyl]benzoate
  参考文献：
  名称：

  Dual RXR Agonists and RAR Antagonists Based on the Stilbene Retinoid Scaffold

  摘要：

  Arotinoids containing a C5,C8-diphenylnaphthalene-2-y1 ring linked to a (C3-halogenated) benzoic acid via an ethenyl connector (but not the corresponding naphthamides), which are prepared by Horner-Wadsworth-Emmons reaction of naphthaldehydes and benzylphosphonates, display the rather unusual property of being RXR agonists (15-fold induction of the RXR reporter cell line was achieved at 3- to 10-fold lower concentration than 9-cis-retinoic acid) and RAR antagonists as shown by transient transactivation studies. The binding of such bulky ligands suggests that the RXR ligand-binding domain is endowed with some degree of structural elasticity.

  DOI：

  10.1021/ml400521f