2-fluoro-4-methoxyphenyl trifluoromethanesulfonate | 550998-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-fluoro-4-methoxyphenyl trifluoromethanesulfonate
• 英文别名: 2-Fluoro-4-methoxyphenyl trifluoromethanesulfonate；(2-fluoro-4-methoxyphenyl) trifluoromethanesulfonate
• CAS: 550998-23-7
• 化学式: C₈H₆F₄O₄S
• 分子量: 274.193
• InChiKey: XELWCBVAXIEQLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-fluoro-4-methoxyphenyl trifluoromethanesulfonate 在 四(三苯基膦)钯 、 三溴化硼 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 生成 6-(2-fluoro-4-hydroxyphenyl)-2-naphthol
  参考文献：
  名称：

  ERβ Ligands. 3. Exploiting Two Binding Orientations of the 2-Phenylnaphthalene Scaffold To Achieve ERβ Selectivity

  摘要：

  The 2-phenylnaphthalene scaffold was explored as a simplified version of genistein in order to identify ER selective ligands. With the aid of docking studies, positions 1, 4, and 8 of the 2-phenylnaphthalene template were predicted to be the most potentially influential positions to enhance ER selectivity using two different binding orientations. Both orientations have the phenol moiety mimicking the A-ring of genistein. Several compounds predicted to adopt orientations similar to that of genistein when bound to ERbeta were observed to have slightly higher ER affinity and selectivity than genistein. The second orientation we exploited, which was different from that of genistein when bound to ERbeta, resulted in the discovery of several compounds that had superior ER selectivity and affinity versus genistein. X-ray structures of two ER selective compounds (i.e., 15 and 47) confirmed the alternate binding mode and suggested that substituents at positions 1 and 8 were responsible for inducing selectivity. One compound (i.e., 47, WAY-202196) was further examined and found to be effective in two models of inflammation, suggesting that targeting ER may be therapeutically useful in treating certain chronic inflammatory diseases.

  DOI：

  10.1021/jm058173s
• 作为产物：
  描述：

  4-溴-2-氟苯酚 在 copper(I) bromide sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-fluoro-4-methoxyphenyl trifluoromethanesulfonate
  参考文献：
  名称：

  Substituted phenyl naphthalenes as estrogenic agents

  摘要：

  这项发明提供了具有结构的式I的雌激素受体调节剂 1 其中 R 1 ，R 2 ，R 3 ，R 4 ，R 5 ，R 6 ，R 7 ，R 8 ，R 9 和R 10 如规范中所定义，或其药用可接受盐。

  公开号：

  US20030181519A1

文献信息

• ERβ Ligands. Part 1: The discovery of ERβ selective ligands which embrace the 4-hydroxy-biphenyl template
  作者：R Edsall

  DOI：10.1016/s0968-0896(03)00303-1

  日期：2003.8.5

  The synthesis and structure-activity relationships of a series of simple biphenyls is described. Optimization of the 4-hydroxy-biphenyl template led to compounds with ERP selectivity on the order of 20-70-fold. (C) 2003 Elsevier Ltd. All rights reserved.
• SUBSTITUTED PHENYL NAPHTHALENES AS ESTROGENIC AGENTS
  申请人：Wyeth

  公开号：EP1453782A2

  公开（公告）日：2004-09-08
• US6914074B2
  申请人：——

  公开号：US6914074B2

  公开（公告）日：2005-07-05
• US7067524B2
  申请人：——

  公开号：US7067524B2

  公开（公告）日：2006-06-27
• [EN] SUBSTITUTED PHENYL NAPHTHALENES AS ESTROGENIC AGENTS<br/>[FR] NAPHTHALENES DE PHENYLE SUBSTITUES EN TANT QU'AGENTS OESTROGENIQUES
  申请人：WYETH CORP

  公开号：WO2003051805A2

  公开（公告）日：2003-06-26

  This invention provides estrogen receptor modulators of formula (I), having the structure (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10, are as defined in the specification, or a pharmaceutically acceptable salt thereof.