3-hydroxy-9β-estra-1,3,5(10)-triene-11,17-dione | 17391-44-5

• 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-hydroxy-9β-estra-1,3,5(10)-triene-11,17-dione
• 英文别名: 11-keto-9β-estrone；3-Hydroxy-9β-oestra-1,3,5(10)-trien-11,17-dion；3-Methoxy-9β-oestra-1,3,5(10)-trien-11,17-dion；Estra-1,3,5(10)-triene-11,17-dione, 3-hydroxy-, (9beta)-；(8S,9R,13S,14S)-3-hydroxy-13-methyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-11,17-dione
• CAS: 17391-44-5
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: WKUQOYYYFVBROI-USJZOSNVSA-N

物化性质

• 熔点：
  204-207 °C (decomp)
• 沸点：
  493.4±45.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-9β-estra-1,3,5(10)-triene-11,17-dione 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 11-keto-9β-estradiol
  参考文献：
  名称：

  Steroid structure and function VII. Remarkable estrogenicity of 3-hydroxy-9β-estra-1,3,5(10)-triene-11,17-dione

  摘要：

  Remarkably high estrogenic activity was observed for 3-hydroxy-9 beta-estra-1,3,5(10)-triene-11,17-dione despite its unusual bent conformation. The 9 alpha epimer of this compound has markedly less activity despite the fact that its overall shape is nearly identical to that of estrone. The potency of these compounds in enhancing uterine weight in Fischer rats and reducing ovarian weight in parabiosed rats was compared with that of estrone, and the structures were unambiguously identified by X-ray crystallographic study. The results underscore the importance of the phenolic ring A to estrogenic activity, and suggest a tolerance of the putative estrogenic receptor to flexibility in overall molecular shape.

  DOI：

  10.1016/0039-128x(80)90046-x
• 作为产物：
  描述：

  乙酸雌酮 在 sodium hydroxide 、 ammonium cerium(IV) nitrate 作用下， 以 吡啶 、 水 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 3-hydroxy-9β-estra-1,3,5(10)-triene-11,17-dione
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1021857108579

文献信息

• Stereochemistry of Steroids containing Aromatic A-Ring. II. Reaction of 9α, 11α-Epoxyestrone.
  作者：Hiroko Hasegawa、Shigeo Nozoe、Kyosuke Tsuda

  DOI：10.1248/cpb.11.1037

  日期：——

  The reduction of 3-hydroxy-9α, 11α-epoxyestra-1, 3, 5 (10)-trien-17-one (III) with lithium aluminum hydride gave estra-1, 3, 5 (10)-triene-3, 11α, 17β-triol. The reaction of III with hydrogen chloride in methanol yielded 3-hydroxy-9β-estra-1, 3, 5 (10)-triene-11, 17-dione (IXa). On the other hand, the reaction in chloroform afforded 9ξ-chloro-3, 11α-dihydroxyestra-1, 3, 5 (10)-trien-17-one (VIIIa). With alkali 3-hydroxyestra-1, 3, 5 (10)-triene-11, 17-dione (Va) is converted into 9β-isomer (IXa).

  3-羟基-9α,11α-环氧雌甾-1,3,5(10)-三烯-17-酮（III）与氢化铝锂反应生成雌甾-1,3,5(10)-三烯-3,11α,17β-三醇。III与甲醇中的氯化氢反应生成3-羟基-9β-雌甾-1,3,5(10)-三烯-11,17-二酮（IXa）。另一方面，在氯仿中的反应生成9ξ-氯-3,11α-二羟基雌甾-1,3,5(10)-三烯-17-酮（VIIIa）。在碱的作用下，3-羟基雌甾-1,3,5(10)-三烯-11,17-二酮（Va）转化为9β-异构体（IXa）。
• RZHEZNIKOV, V. M., BIOORGAN. XIMIYA, 17,(1991) N, S. 1002-1004
  作者：RZHEZNIKOV, V. M.

  DOI：——

  日期：——
• ——
  作者：L. E. Golubovskaya、O. N. Minailova、V. M. Rzheznikov

  DOI：10.1023/a:1021857108579

  日期：——
• Steroid structure and function VII. Remarkable estrogenicity of 3-hydroxy-9β-estra-1,3,5(10)-triene-11,17-dione
  作者：Albert Segaloff、R.Bruce Gabbard、Albert Flores、Ronald F. Borne、John K. Baker、William L. Duax、Phyllis D. Strong、Douglas C. Rohrer

  DOI：10.1016/0039-128x(80)90046-x

  日期：1980.3

  Remarkably high estrogenic activity was observed for 3-hydroxy-9 beta-estra-1,3,5(10)-triene-11,17-dione despite its unusual bent conformation. The 9 alpha epimer of this compound has markedly less activity despite the fact that its overall shape is nearly identical to that of estrone. The potency of these compounds in enhancing uterine weight in Fischer rats and reducing ovarian weight in parabiosed rats was compared with that of estrone, and the structures were unambiguously identified by X-ray crystallographic study. The results underscore the importance of the phenolic ring A to estrogenic activity, and suggest a tolerance of the putative estrogenic receptor to flexibility in overall molecular shape.