2-羟基-4-(4-甲氧基苯基)苯甲醛 | 1014625-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-羟基-4-(4-甲氧基苯基)苯甲醛
• 英文名称: 4-(4-methoxyphenyl)salicylaldehyde
• 英文别名: 2-hydroxy-4-(4'-methoxyphenyl)benzaldehyde；2-Formyl-5-(4-methoxyphenyl)phenol；2-hydroxy-4-(4-methoxyphenyl)benzaldehyde
• CAS: 1014625-93-4
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: SGXOELUJXLGAAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-羟基-4-(4-甲氧基苯基)苯甲醛 在 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以87%的产率得到4-(4-Methoxyphenyl)salicylaldoxime
  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
• 作为产物：
  描述：

  (E/Z)-5-(4-methoxyphenyl)-2-(prop-1-enyl)phenol 在 四氧化锇 sodium periodate 作用下， 以 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 反应 2.0h， 以87%的产率得到2-羟基-4-(4-甲氧基苯基)苯甲醛
  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

文献信息

• Dual‐State Emissive π‐Extended Salicylaldehyde Fluorophores: Synthesis, Photophysical Properties and First‐Principle Calculations
  作者：Timothée Stoerkler、Denis Frath、Denis Jacquemin、Julien Massue、Gilles Ulrich

  DOI：10.1002/ejoc.202100650

  日期：2021.7.15

  The synthesis and photophysical properties of a series of functionalized salicylaldehydes derivatives are reported. The compounds show strong fluorescence intensity in solution and in the solid state in various environments. The results are rationalized by ab initio calculations.

  报道了一系列功能化水杨醛衍生物的合成和光物理性质。这些化合物在溶液中和在各种环境中的固态中都显示出很强的荧光强度。结果通过 ab initio 计算合理化。
• 1,2,3-Benzoxathiazine-2,2-dioxides – effective inhibitors of human carbonic anhydrases
  作者：Jekaterina Ivanova、Morteza Abdoli、Alessio Nocentini、Raivis Žalubovskis、Claudiu T. Supuran

  DOI：10.1080/14756366.2022.2142787

  日期：2023.1.1

  inhibitors of hCA IX and XII. Almost all compounds except 2d and 5a-e also express nanomolar inhibitory activity for hCA II. hCA I is poorly inhibited or not inhibited by 1,2,3-benzoxathiazine 2,2-dioxides. Some of the new derivatives exhibit promising selectivity towards CA IX/XII over hCA I, although none of the compounds are selective towards CA IX/XII over both hCA I and II.

  摘要 一系列在 5、7 或 8 位具有不同取代基的 1,2,3-苯并恶噻嗪-2,2-二氧化物是由相应的 2-羟基苯甲醛与氨磺酰氯反应得到的。5-、7- 和 8-芳基取代的 1,2,3-苯并恶噻嗪-2,2-二氧化物是从 3-、4- 或 6-溴-2-羟基苯甲醛获得的芳基取代的 2-羟基苯甲醛通过两种方法制备的步协议。研究了 1,2,3-Benzoxathiazine-2,2-dioxides 对四种人碳酸酐酶 (hCA, EC 4.2.1.1) 亚型、胞质 hCA I 和 II 以及肿瘤相关跨膜 hCA IX 和 XII 的抑制作用。获得了 1,2,3-苯并恶噻嗪 2,2-二氧化物的 24 个衍生物。它们中的大多数充当 hCA IX 和 XII 的纳摩尔抑制剂。几乎所有的化合物除了2d和5a-e还表达了对 hCA II 的纳摩尔抑制活性。hCA I 很少被 1,2,3-苯并恶噻嗪 2,2-二氧化物抑制或不被抑制。一些新的衍生物对
• Monoaryl-Substituted Salicylaldoximes as Ligands for Estrogen Receptor β
  作者：Filippo Minutolo、Rosalba Bellini、Simone Bertini、Isabella Carboni、Annalina Lapucci、Letizia Pistolesi、Giovanni Prota、Simona Rapposelli、Francesca Solati、Tiziano Tuccinardi、Adriano Martinelli、Fabio Stossi、Kathryn E. Carlson、Benita S. Katzenellenbogen、John A. Katzenellenbogen、Marco Macchia

  DOI：10.1021/jm701396g

  日期：2008.3.13

  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.