(8S,9S,13S,14S)-10-hydroxy-13-methyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[a]phenanthrene-3,17(6H)-dione | 109581-81-9

• 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: (8S,9S,13S,14S)-10-hydroxy-13-methyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[a]phenanthrene-3,17(6H)-dione
• 英文别名: 10-hydroxy-13-methyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[a]phenanthrene-3,17(6H)-dione；17-Oxo-oestra-p-chinol-(10ξ)；(8S,9S,13S,14S)-10-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 109581-81-9
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: RVUDOXUDSXVAEV-FVJHYMBVSA-N

物化性质

• 熔点：
  215-217 °C
• 沸点：
  485.2±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (8S,9S,13S,14S)-10-hydroxy-13-methyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[a]phenanthrene-3,17(6H)-dione 在 溶剂黄146 作用下， 以 乙二醇甲醚 为溶剂， 生成 N-((8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)acetamide
  参考文献：
  名称：

  Hecker,E.; Walk,E., Chemische Berichte, 1960, vol. 93, p. 2928 - 2937

  摘要：

  DOI：
• 作为产物：
  描述：

  17-Oxo-oestra-p-chinol-(10ξ)-acetat 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (8S,9S,13S,14S)-10-hydroxy-13-methyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[a]phenanthrene-3,17(6H)-dione
  参考文献：
  名称：

  Hecker,E.; Walk,E., Chemische Berichte, 1960, vol. 93, p. 2928 - 2937

  摘要：

  DOI：

文献信息

• Photocatalytic Synthesis of <i>para</i>-Peroxyquinols: Total Synthesis of (±)-Stemenone B and (±)-Parvistilbine B
  作者：Matthew C. Carson、Brandon J. Orzolek、Marisa C. Kozlowski

  DOI：10.1021/acs.orglett.2c02640

  日期：2022.10.14

  photosensitized singlet oxygen approach functionalized a variety of electronically diverse para-alkyl phenols in 27–99% isolated yields. Utilizing this dearomative oxidation, (±)-stemenone B and (±)-parvistilbine B were synthesized in 9 and 11 steps, respectively, from commercially available starting materials. Additional experiments revealed the dramatic influence of base and solvent on the selectivity

  公开了一种从对烷基苯酚选择性合成4-氢过氧-2,5-环己二酮的光催化方法。这种光敏单线态氧方法以 27-99% 的分离产率对多种电子多样化的对烷基酚进行官能化。利用这种脱芳香氧化，从市售起始材料分别通过 9 和 11 个步骤合成了 (±)-百叶酮 B 和 (±)-parvistilbine B。其他实验揭示了碱和溶剂对选择性的巨大影响，同时提供了对这种转化机制的深入了解。
• A Green Blue LED-Driven Two-Liquid-Phase One-Pot Procedure for the Synthesis of Estrogen-Related Quinol Prodrugs
  作者：Elisa De Marchi、Lorenzo Botta、Bruno Mattia Bizzarri、Raffaele Saladino

  DOI：10.3390/molecules27248961

  日期：——

  therapy. Here, we report that these compounds can be synthesized in one-pot conditions and high yield by blue LED-driven photo-oxygenation of parent estrogens. The oxidation was performed in buffer and eco-certified 2-methyltetrahydrofuran as the two-liquid-phase reaction solvent, and in the presence of meso-tetraphenyl porphyrin as the photosensitizer. Two steroidal prodrugs 10β, 17β-dihydroxyestra-1,4-dien-3-one

  雌激素的喹酚衍生物是类固醇替代疗法中的有效前药。在这里，我们报告说，这些化合物可以在一锅条件下合成，并通过蓝色 LED 驱动的母体雌激素光氧化实现高产率。氧化是在缓冲液中进行的，生态认证的 2-甲基四氢呋喃作为双液相反应溶剂，并在内消旋四苯基卟啉作为光敏剂存在的情况下进行。以高产率和选择性获得了两种甾体前药 10β, 17β-dihydroxyestra-1,4-dien-3-one (DHED) 和 10β-Hydroxyestra-1,4-diene-3,17-dione (HEDD)。
• Steroidal quinols and their use for estrogen replacement therapy
  申请人：——

  公开号：US20040138190A1

  公开（公告）日：2004-07-15

  The present invention relates to novel estrogen-related steroidal quinols and their use as drugs for estrogen replacement therapy. The quinols of the present invention provide improved physicochemical properties, increased bioavailability, and improved distribution into tissues, bone, in the cardiovascular system, and in the CNS (central nervous system) with only a slight estrogenic action or no estrogenic action in the uterus. The compounds are suitable for the production of pharmaceutical agents for use in numerous indications (for example, estrogen replacement therapy, prevention and treatment of osteoporosis).

  本发明涉及新型雌激素相关类固醇喹啉及其作为雌激素替代疗法药物的用途。本发明的喹啉具有更好的理化性质、更高的生物利用度，以及在组织、骨骼、心血管系统和 CNS（中枢神经系统）中更好的分布，在子宫中只有轻微的雌激素作用或没有雌激素作用。这些化合物适合生产用于多种适应症（如雌激素替代疗法、预防和治疗骨质疏松症）的药剂。
• Lupon, Pilar; Gomez, Jose; Bonet, Juan-Julio, Angewandte Chemie, 1983, vol. 95, # 9, p. 757
  作者：Lupon, Pilar、Gomez, Jose、Bonet, Juan-Julio

  DOI：——

  日期：——