(E/Z)-6-chloro-2-hydroxy-3-(prop-1-enyl)benzonitrile | 1014626-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E/Z)-6-chloro-2-hydroxy-3-(prop-1-enyl)benzonitrile
• 英文别名: 6-chloro-2-hydroxy-3-prop-1-enylbenzonitrile
• CAS: 1014626-07-3
• 化学式: C₁₀H₈ClNO
• 分子量: 193.633
• InChiKey: HFRDCYURVYWGEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E/Z)-6-chloro-2-hydroxy-3-(prop-1-enyl)benzonitrile 、 4-甲氧基苯硼酸 在 tris(dibenzylideneacetone)dipalladium (0) 、 三环己基膦 caesium carbonate 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 0.5h， 生成 (Z)-2-hydroxy-6-(4-methoxyphenyl)-3-(prop-1-enyl)benzonitrile 、 (E)-2-hydroxy-6-(4-methoxyphenyl)-3-(prop-1-enyl)benzonitrile
  参考文献：
  名称：

  Monoaryl-Substituted Salicylaldoximes as Ligands for Estrogen Receptor β

  摘要：

  Salicylaldoximes possess a hydrogen-bonded pseudocyclic A' ring in place of the typical phenolic A ring that is characteristic of most estrogen receptor (ER) ligands. Monoaryl-substituted salicylaldoximes were obtained by replacing the phenol moiety (ring A) of the ER beta pharmacophore with the pseudocycle A' ring, which has previously been shown to behave as a bioequivalent of phenols in nonselective ER ligands. In this series, small substituents (CH(3), CN, Cl) were introduced into the central phenyl scaffold. An efficient sequential halogen-selective double cross-coupling reaction was developed for the synthesis of the methylsubstituted ER ligand. The measured ER beta affinity proved to be very sensitive to the effect of central core substituents. The binding affinities of the compounds herein reported were in good agreement with the results of computational docking analysis. The chloro-substituted derivative showed the highest beta affinity and selectivity, and it also proved to be an ER beta partial agonist with an EC(50) of 11 nM.

  DOI：

  10.1021/jm701396g