4-bromo-3-acetoxyestra-1,3,5(10)-trien-17-one | 94758-08-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 4-bromo-3-acetoxyestra-1,3,5(10)-trien-17-one
• 英文别名: acetate of 4-monobromoestrone；4-Brom-3-acetoxy-17-oxo-oestratrien-(1,3,5(10))
• CAS: 94758-08-4
• 化学式: C₂₀H₂₃BrO₃
• 分子量: 391.305
• InChiKey: DBCKHLKHWIOFEQ-NKSTXHLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-bromo-3-acetoxyestra-1,3,5(10)-trien-17-one 在 bis-triphenylphosphine-palladium(II) chloride 、 四甲基锡 、 三苯基膦 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以83%的产率得到4-methyl-3-acetoxyestra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  18F-labelling of A-ring substituted 16α-fluoro-estradiols as potential radiopharmaceuticals for PET imaging

  摘要：

  The 2-methoxy derivative of estradiol is currently in Phase II clinical trial as an anticancer agent while the 4-methyl derivative has been shown to interact with cytoplasmic and nuclear estrogen receptors in rat pituitary gland and hypothalamus. We hypothesize that the 16 alpha-F-18-analogs of these estrogens could be suitable radiotracers to evaluate action mechanisms of the parent compounds. In this study we report the synthesis of the 16 alpha-F-18 and 16 alpha-F-19-analogs of the A-ring substituted estradiols in high yield via stereoselective opening of the inter-mediate 16 beta,17 beta-O-cyclic sulfones with [F-18]F- or F- followed by deprotection. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.09.006
• 作为产物：
  描述：

  4-溴雌酮 在 4-二甲氨基吡啶 、 乙酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以96%的产率得到4-bromo-3-acetoxyestra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  18F-labelling of A-ring substituted 16α-fluoro-estradiols as potential radiopharmaceuticals for PET imaging

  摘要：

  The 2-methoxy derivative of estradiol is currently in Phase II clinical trial as an anticancer agent while the 4-methyl derivative has been shown to interact with cytoplasmic and nuclear estrogen receptors in rat pituitary gland and hypothalamus. We hypothesize that the 16 alpha-F-18-analogs of these estrogens could be suitable radiotracers to evaluate action mechanisms of the parent compounds. In this study we report the synthesis of the 16 alpha-F-18 and 16 alpha-F-19-analogs of the A-ring substituted estradiols in high yield via stereoselective opening of the inter-mediate 16 beta,17 beta-O-cyclic sulfones with [F-18]F- or F- followed by deprotection. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.09.006

文献信息

• Influence of a substituent at C3 on the direction of bromination of estra-1,3,5(10)trien-17-ones
  作者：O. I. Fedorova、L. S. Morozova、L. M. Alekseeva、G. S. Grinenko

  DOI：10.1007/bf00575753

  日期：——