2-(4-Benzyloxy-2-fluoro-6-hydroxy-phenylsulfanyl)-1-(4-hydroxy-phenyl)-2-(4-triisopropylsilanyloxy-phenyl)-ethanone | 412051-60-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(4-Benzyloxy-2-fluoro-6-hydroxy-phenylsulfanyl)-1-(4-hydroxy-phenyl)-2-(4-triisopropylsilanyloxy-phenyl)-ethanone
• 英文别名: 2-(2-Fluoro-6-hydroxy-4-phenylmethoxyphenyl)sulfanyl-1-(4-hydroxyphenyl)-2-[4-tri(propan-2-yl)silyloxyphenyl]ethanone
• CAS: 412051-60-6
• 化学式: C₃₆H₄₁FO₅SSi
• 分子量: 632.868
• InChiKey: XAMXRMVJJOKFJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.09
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(4-Benzyloxy-2-fluoro-6-hydroxy-phenylsulfanyl)-1-(4-hydroxy-phenyl)-2-(4-triisopropylsilanyloxy-phenyl)-ethanone 在 三乙基硅烷 、 三氟乙酸 作用下， 生成 4-[(2R,3S)-7-Benzyloxy-5-fluoro-3-(4-triisopropylsilanyloxy-phenyl)-2,3-dihydro-benzo[1,4]oxathiin-2-yl]-phenol
  参考文献：
  名称：

  Estrogen receptor ligands. Part 4: The SAR of the syn-dihydrobenzoxathiin SERAMs

  摘要：

  A series of estrogen receptor ligands based on a dihydrobenzoxathiin scaffold is described and evaluated for estrogen/anti-estrogen activity in both in vitro and in vivo models. The most active analogue, 22, was found to be 40-fold ERalpha selective in a competitive binding assay, and 22 demonstrated very potent in vivo antagonism of estradiol driven proliferation in an immature rat uterine weight gain assay. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.074
• 作为产物：
  描述：

  5-Benzyloxy-3-fluoro-2-mercapto-phenol 、 4'-hydroxy-2-bromo-2-(4-triisopropylsilyloxy-phenyl)-acetophenone 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(4-Benzyloxy-2-fluoro-6-hydroxy-phenylsulfanyl)-1-(4-hydroxy-phenyl)-2-(4-triisopropylsilanyloxy-phenyl)-ethanone
  参考文献：
  名称：

  Estrogen receptor ligands. Part 4: The SAR of the syn-dihydrobenzoxathiin SERAMs

  摘要：

  A series of estrogen receptor ligands based on a dihydrobenzoxathiin scaffold is described and evaluated for estrogen/anti-estrogen activity in both in vitro and in vivo models. The most active analogue, 22, was found to be 40-fold ERalpha selective in a competitive binding assay, and 22 demonstrated very potent in vivo antagonism of estradiol driven proliferation in an immature rat uterine weight gain assay. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.074

文献信息

• Dehydrative Reduction:  A Highly Diastereoselective Synthesis of <i>syn</i>-Bisaryl(or Heteroaryl) Dihydrobenzoxathiins and Benzodioxane
  作者：Seongkon Kim、Jane Y. Wu、Helen Y. Chen、Frank DiNinno

  DOI：10.1021/ol0274763

  日期：2003.3.1

  [GRAPHICS]TFA/Et3SIH-mediated cyclization of thioketones 5 derived from the reaction of functionalized thiophenols (catechols) with bromo ketones gave syn 2,3-bisaryl(or heteroaryl) dihydrobenzoxathiins and benzodioxane 1 with total diastereoselectivity (>99:1), in excellent yields.