2-(3-iodo-1H-indol-2-yl)phenol | 941573-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(3-iodo-1H-indol-2-yl)phenol
• CAS: 941573-94-0
• 化学式: C₁₄H₁₀INO
• 分子量: 335.144
• InChiKey: REIURIRVMHBMFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.02
• 氢给体数：
  2.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(3-iodo-1H-indol-2-yl)phenol 、 炔雌醇 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 (8R,9S,13S,14S,17S)-17-(2-(2-(2-hydroxyphenyl)-1H-indol-3-yl)ethynyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
  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：

  2-氨基苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 碘 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 2-(3-iodo-1H-indol-2-yl)phenol
  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