3,17β-Bis-(tert.-butyloxy)-oestratrien-(1,3,5(10)) | 1852-96-6

• 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: 3,17β-Bis-(tert.-butyloxy)-oestratrien-(1,3,5(10))
• 英文别名: 3,17β-Bis(tert-butoxy)estra-1,3,5(10)-trien；(8R,9S,13S,14S,17S)-13-methyl-3,17-bis[(2-methylpropan-2-yl)oxy]-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene
• CAS: 1852-96-6
• 化学式: C₂₆H₄₀O₂
• 分子量: 384.602
• InChiKey: JHCWDSMEKKDJSO-IOCWQACJSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  471.6±45.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,17β-Bis-(tert.-butyloxy)-oestratrien-(1,3,5(10)) 在 2,2,6,6-tetramethyl-piperidine-N-oxyl sodium hypochlorite 、 potassium tert-butylate 、 碳酸氢钠 、 potassium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 (8R,9S,13S,14S,17S)-13-methyl-3,17-bis[(2-methylpropan-2-yl)oxy]-8,9,11,12,14,15,16,17-octahydro-7H-cyclopenta[a]phenanthren-6-one
  参考文献：
  名称：

  Synthesis of Chimeric 7α-Substituted Estradiol Derivatives Linked to Cholesterol and Cholesterylamine

  摘要：

  We report the synthesis of 7alpha-substituted beta-estradiol derivatives bearing side chains terminated with cholesterol and 3beta-cholesterylamine. These chimeric compounds were designed to exhibit high affinity for estrogen receptors (ERs) and cellular plasma membranes to potentially enable regulated uptake of ERs by mammalian cells. Evaluation with recombinant yeast reporting compound-mediated ER dimerization revealed potencies similar to the antiestrogen ICI 182780. Compounds that efficiently deliver dominant negative ERs into cells may provide novel therapeutics against breast cancers.

  DOI：

  10.1021/ol0171261
• 作为产物：
  描述：

  雌二醇 、 异丁烯 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 3,17β-Bis-(tert.-butyloxy)-oestratrien-(1,3,5(10))
  参考文献：
  名称：

  Cherkasov,A.N. et al., Journal of Organic Chemistry USSR (English Translation), 1974, vol. 10, p. 321 - 328

  摘要：

  DOI：

文献信息

• Synthesis of Chimeric 7α-Substituted Estradiol Derivatives Linked to Cholesterol and Cholesterylamine
  作者：Stephen L. Hussey、Enfei He、Blake R. Peterson

  DOI：10.1021/ol0171261

  日期：2002.2.1

  We report the synthesis of 7alpha-substituted beta-estradiol derivatives bearing side chains terminated with cholesterol and 3beta-cholesterylamine. These chimeric compounds were designed to exhibit high affinity for estrogen receptors (ERs) and cellular plasma membranes to potentially enable regulated uptake of ERs by mammalian cells. Evaluation with recombinant yeast reporting compound-mediated ER dimerization revealed potencies similar to the antiestrogen ICI 182780. Compounds that efficiently deliver dominant negative ERs into cells may provide novel therapeutics against breast cancers.
• Cherkasov,A.N. et al., Journal of Organic Chemistry USSR (English Translation), 1974, vol. 10, p. 321 - 328
  作者：Cherkasov,A.N. et al.

  DOI：——

  日期：——