(E)-4-(3,3-dimethyl-but-1-E-en-1-yl)-3,5-bis(4-hydroxyphenyl )isoxazole | 1400414-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-4-(3,3-dimethyl-but-1-E-en-1-yl)-3,5-bis(4-hydroxyphenyl )isoxazole
• 英文别名: 4-[4-[(E)-3,3-dimethylbut-1-enyl]-3-(4-hydroxyphenyl)-1,2-oxazol-5-yl]phenol
• CAS: 1400414-32-5
• 化学式: C₂₁H₂₁NO₃
• 分子量: 335.403
• InChiKey: DEQQENRRDZKAGR-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-双(4-甲氧基苯基)1,3-丙二酮 在 bis-triphenylphosphine-palladium(II) chloride 、 N-碘代丁二酰亚胺 、 盐酸羟胺 、 水 、 碘 、 三溴化硼 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 164.5h， 生成 (E)-4-(3,3-dimethyl-but-1-E-en-1-yl)-3,5-bis(4-hydroxyphenyl )isoxazole
  参考文献：
  名称：

  Synthesis and evaluation of 4-(substituted styryl/alkenyl)-3,5-bis(4-hydroxyphenyl)-isoxazoles as ligands for the estrogen receptor

  摘要：

  A series of 3,5-bis(4-hydroxyphenyl) isoxazoles bearing a styryl/alkyl vinyl group at the 4-position were prepared and evaluated as ligands for the estrogen receptor-alpha (ER alpha). The target compounds were prepared using the Suzuki reaction to couple an iodo-isoxazole intermediate with a series of styryl/alkenyl boronic acids, followed by O-demethylation. The products were evaluated for their estrogen receptor-alpha ligand binding domain (ER alpha-LBD) binding affinity using a competitive binding assay. The 4-(4-hydroxy-styryl) derivative 4 h displays binding properties similar to those of the previously described pyrazole class of ER ligands, indicating that the ER alpha-LBD tolerates the presence of the added vinyl group at the 4-position of the isoxazole ring. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.097

文献信息

• Synthesis and evaluation of 4-(substituted styryl/alkenyl)-3,5-bis(4-hydroxyphenyl)-isoxazoles as ligands for the estrogen receptor
  作者：Terra Haddad、Rachel Gershman、Robert Dilis、David Labaree、Richard B. Hochberg、Robert N. Hanson

  DOI：10.1016/j.bmcl.2012.06.097

  日期：2012.9

  A series of 3,5-bis(4-hydroxyphenyl) isoxazoles bearing a styryl/alkyl vinyl group at the 4-position were prepared and evaluated as ligands for the estrogen receptor-alpha (ER alpha). The target compounds were prepared using the Suzuki reaction to couple an iodo-isoxazole intermediate with a series of styryl/alkenyl boronic acids, followed by O-demethylation. The products were evaluated for their estrogen receptor-alpha ligand binding domain (ER alpha-LBD) binding affinity using a competitive binding assay. The 4-(4-hydroxy-styryl) derivative 4 h displays binding properties similar to those of the previously described pyrazole class of ER ligands, indicating that the ER alpha-LBD tolerates the presence of the added vinyl group at the 4-position of the isoxazole ring. (c) 2012 Elsevier Ltd. All rights reserved.