2-(4-(benzyloxy)phenyl)-3-iodobenzofuran-6-yl 4-methylbenzenesulfonate | 941573-96-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(4-(benzyloxy)phenyl)-3-iodobenzofuran-6-yl 4-methylbenzenesulfonate
• CAS: 941573-96-2
• 化学式: C₂₈H₂₁IO₅S
• 分子量: 596.442
• InChiKey: CUHDAHVRIIYIGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.36
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  65.74
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  17α-(1,7-octadiyn-1-yl)estradiol 、 2-(4-(benzyloxy)phenyl)-3-iodobenzofuran-6-yl 4-methylbenzenesulfonate 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-(4-(benzyloxy)phenyl)-3-(8-((8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)octa-1,7-diynyl)benzofuran-6-yl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis, characterization, and estrogen receptor binding affinity of flavone-, indole-, and furan-estradiol conjugates

  摘要：

  Different flavone-, indole-, and furan-17 beta-estradiol conjugates, linked via alkyl spacer chains extending from the 17 alpha-position of the estradiol moiety, were synthesized by Pd-catalyzed cross-coupling reactions. Structures were assigned based on spectroscopic data. In vitro competitive binding assays for the estrogen receptor (alpha-ER), using [H-3]estradiol (RBA = 100) as a competitor, revealed that a two-carbon alkyl linker combined with a flavone conjugate provided the highest binding affinity (RBA similar to 9), warranting further studies on their potential use as selective estrogen-receptor modulators (SERMs) for hormone-replacement therapies. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.016
• 作为产物：
  描述：

  4-((4-(benzyloxy)phenyl)ethynyl)-3-methoxyphenyl 4-methylbenzenesulfonate 在 碘 作用下， 以 二氯甲烷 为溶剂， 生成 2-(4-(benzyloxy)phenyl)-3-iodobenzofuran-6-yl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis, characterization, and estrogen receptor binding affinity of flavone-, indole-, and furan-estradiol conjugates

  摘要：

  Different flavone-, indole-, and furan-17 beta-estradiol conjugates, linked via alkyl spacer chains extending from the 17 alpha-position of the estradiol moiety, were synthesized by Pd-catalyzed cross-coupling reactions. Structures were assigned based on spectroscopic data. In vitro competitive binding assays for the estrogen receptor (alpha-ER), using [H-3]estradiol (RBA = 100) as a competitor, revealed that a two-carbon alkyl linker combined with a flavone conjugate provided the highest binding affinity (RBA similar to 9), warranting further studies on their potential use as selective estrogen-receptor modulators (SERMs) for hormone-replacement therapies. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.016