3-羟基-9beta-雌甾-1,3,5(10)-三烯-11,17-二酮 | 7533-97-3

• 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
• 中文名称: 3-羟基-9beta-雌甾-1,3,5(10)-三烯-11,17-二酮
• 中文别名: 2-(2,4-二硝基苯基)硫烷基乙酸,2-(2-羟基乙胺基)乙烷醇
• 英文名称: 11-Ketoestrone
• 英文别名: 11-Ketooestron；3-Hydroxy-oestra-1,3,5(10)-trien-11,17-dion；3-Hydroxy-9 beta-estra-1,3,5(10)-triene-11,17-dione；(8S,9S,13S,14S)-3-hydroxy-13-methyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-11,17-dione
• CAS: 7533-97-3
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: WKUQOYYYFVBROI-ZZCKCESHSA-N

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-羟基-9beta-雌甾-1,3,5(10)-三烯-11,17-二酮 在 甲醇 、 氢氧化钾 作用下， 生成 3-hydroxy-9β-estra-1,3,5(10)-triene-11,17-dione
  参考文献：
  名称：

  Stereochemistry of Steroids containing Aromatic A-Ring. II. Reaction of 9α, 11α-Epoxyestrone.

  摘要：

  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）。

  DOI：

  10.1248/cpb.11.1037
• 作为产物：
  描述：

  11beta-Hydroxyestrone 在 chromium(VI) oxide 、 硫酸 作用下， 生成 3-羟基-9beta-雌甾-1,3,5(10)-三烯-11,17-二酮
  参考文献：
  名称：

  Stereochemistry of Steroids containing Aromatic A-Ring. II. Reaction of 9α, 11α-Epoxyestrone.

  摘要：

  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）。

  DOI：

  10.1248/cpb.11.1037

文献信息

• Demethylaromatization of cyclohexadienones by iodotriphenylphosphonium iodide
  作者：Guanghui Chen、Yong Shi、Weisheng Tian、Hongyan Xie、Zhaohua Yan、Junmin Yu

  DOI：10.1016/j.tetlet.2023.154365

  日期：2023.3

  A highly efficient and metal-free demethylation and concomitant aromatization of cyclohexadienones using iodotriphenylphosphonium iodide was developed. A variety of steroidal and non-steroidal substrates smoothly underwent demethylaromatization reaction generating the corresponding phenolic products in good yields. This approach exhibits broad functional group tolerance. An ionic mechanism of synergistic

  开发了使用碘化三苯基磷碘化物对环己二烯酮进行高效且无金属的去甲基化和伴随的芳构化。多种甾体和非甾体底物顺利进行去甲基芳构化反应，以良好的收率生成相应的酚类产物。这种方法表现出广泛的功能组耐受性。提出了协同作用的离子机制。该方法在 1,4-androstadiene-3,17-dione 一步转化为 3-hydroxy-1,3,5(10)-estratrien-17-one 过程中显示出潜在的工业价值一系列甾体避孕药。
• 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.
• STEROID ADMINISTRATION AND IMMUNOTHERAPY
  申请人：Intrexon Corporation

  公开号：EP3548047A1

  公开（公告）日：2019-10-09
• [EN] METHODS FOR COMPREHENSIVE PROFILING OF STEROID METABOLOME<br/>[FR] PROCÉDÉS POUR UN PROFILAGE COMPLET D'UN MÉTABOLOME STÉROÏDIEN
  申请人：UNIV CALIFORNIA

  公开号：WO2015161078A1

  公开（公告）日：2015-10-22

  The present invention provides a method for quantitating at least 100 steroids in a biological sample using ultra-performance liquid chromatography-tandem mass spectrometry. The present invention also provides a method for detecting an imbalance in steroid metabolism or the presence of cancer in an individual.
• [EN] STEROID ADMINISTRATION AND IMMUNOTHERAPY<br/>[FR] ADMINISTRATION DE STÉROÏDES ET IMMUNOTHÉRAPIE
  申请人：INTREXON CORP

  公开号：WO2018102606A1

  公开（公告）日：2018-06-07

  Disclosed herein include methods of inducing expansion of modified effector cells in vivo which comprise administration of a steroid and modified effector cells. Also described herein include methods of inducing expansion of modified T cells (e.g., CAR-T cells or TCR cells) in vivo, which comprise administration of a steroid and modified T cells.