3-(4-甲氧基苯基)-2-甲基苯酚 | 1014625-96-7

• 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: 3-(4-甲氧基苯基)-2-甲基苯酚
• 英文名称: 3-(4-methoxyphenyl)-2-methylphenol
• CAS: 1014625-96-7
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: FJSRTXFSPOLFEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯-3-(4-甲氧基苯基)苯酚 、 甲基硼酸 在 palladium diacetate potassium phosphate 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以52%的产率得到3-(4-甲氧基苯基)-2-甲基苯酚
  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

• Synthesis of multisubstituted phenols by formal [4 + 2] cycloaddition of nucleophilic alkynes with 3-ethoxycyclobutanones
  作者：Takeo Kuzuguchi、Yuto Yabuuchi、Tomoyuki Yoshimura、Jun-ichi Matsuo

  DOI：10.1039/c7ob00827a

  日期：——

  Nucleophilic alkynes bearing sulfonamide, trimethylsilyl, or p-methoxyphenyl groups at the sp carbon reacted with 3-ethoxycyclobutanones to give formal [4+2] cycloadducts by activation with TiCl4. Reactions with 2-monoalkyl and 2-nonsubstituted 3-ethoxycyclobutanones gave phenol derivatives directly by benzannulation, while the use of 2,2-dimethyl-3-ethoxycyclobutanone gave the corresponding dienones

  在sp碳上带有磺酰胺，三甲基甲硅烷基或对甲氧基苯基的亲核炔烃与3-乙氧基环丁酮反应，经TiCl4活化，生成正式的[4 + 2]环加合物。与2-单烷基和2-非取代的3-乙氧基环丁酮的反应直接通过苯环烷基化得到苯酚衍生物，而使用2,2-二甲基-3-乙氧基环丁酮产生相应的二烯酮，它们通过二烯酮-苯酚重排转化为五取代的苯酚。还描述了取决于二烯酮-苯酚重排的活化条件的区域选择性。
• 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.