5-chloro-4,4'-dihydroxy-2-methylbiphenyl-3-carbaldehyde | 1310800-72-6

• 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: 5-chloro-4,4'-dihydroxy-2-methylbiphenyl-3-carbaldehyde
• 英文别名: 3-Chloro-2-hydroxy-5-(4-hydroxyphenyl)-6-methylbenzaldehyde
• CAS: 1310800-72-6
• 化学式: C₁₄H₁₁ClO₃
• 分子量: 262.693
• InChiKey: CRMQZLPUBQVLOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-4,4'-dihydroxy-2-methylbiphenyl-3-carbaldehyde 在 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以79%的产率得到(E)-5-chloro-4,4'-dihydroxy-2-methylbiphenyl-3-carbaldehyde oxime
  参考文献：
  名称：

  Selective and potent agonists for estrogen receptor beta derived from molecular refinements of salicylaldoximes

  摘要：

  In a continuing effort to improve the subtype selectivity and agonist potency of estrogen receptor beta (ER beta) ligands, we have designed and developed a thus far unexplored structural series obtained by molecular refinements of monoaryl-substituted salicylaldoximes (Salaldox B). The most interesting compounds in this series (2c, d) show remarkably high ER beta-binding affinities, with K(i) values reaching the sub-nanomolar range (K(i) = 0.38 nM for 2c and 0.57 nM for 2d), and have very high levels of ER beta-subtype selectivity. Both compounds show a potent full agonist character on ER beta (EC(50) = 0.23 nM for 2c and 1.3 nM for 2d). Furthermore, 2d shows a remarkable functional subtype selectivity, with a beta/alpha transcription potency ratio 50-fold higher than that of estradiol. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.030
• 作为产物：
  描述：

  3-氯-2-羟基-6-甲基苯甲醛 在 溴 、 palladium diacetate 、 三溴化硼 、 sodium carbonate 、 potassium carbonate 、 溶剂黄146 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 65.08h， 生成 5-chloro-4,4'-dihydroxy-2-methylbiphenyl-3-carbaldehyde
  参考文献：
  名称：

  Selective and potent agonists for estrogen receptor beta derived from molecular refinements of salicylaldoximes

  摘要：

  In a continuing effort to improve the subtype selectivity and agonist potency of estrogen receptor beta (ER beta) ligands, we have designed and developed a thus far unexplored structural series obtained by molecular refinements of monoaryl-substituted salicylaldoximes (Salaldox B). The most interesting compounds in this series (2c, d) show remarkably high ER beta-binding affinities, with K(i) values reaching the sub-nanomolar range (K(i) = 0.38 nM for 2c and 0.57 nM for 2d), and have very high levels of ER beta-subtype selectivity. Both compounds show a potent full agonist character on ER beta (EC(50) = 0.23 nM for 2c and 1.3 nM for 2d). Furthermore, 2d shows a remarkable functional subtype selectivity, with a beta/alpha transcription potency ratio 50-fold higher than that of estradiol. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.030