D-17β-acetoxy-3-methoxy-14α-estra-1,3,5(10),6,8-pentaene | 73610-78-3

• 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
• 英文名称: D-17β-acetoxy-3-methoxy-14α-estra-1,3,5(10),6,8-pentaene
• 英文别名: 17β-acetoxy-3-methoxyestra-1,3,5,7,9-pentaene；17beta-Acetoxy-3-methoxyestra-1,3,5,7,9-pentaene；[(13S,14S,17S)-3-methoxy-13-methyl-11,12,14,15,16,17-hexahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 73610-78-3
• 化学式: C₂₁H₂₄O₃
• 分子量: 324.42
• InChiKey: JCRFIZBVXKZZHN-ACRUOGEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D-17β-acetoxy-3-methoxy-14α-estra-1,3,5(10),6,8-pentaene 在 氢氧化钾 、 jones' reagent 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 为溶剂， 反应 0.83h， 生成 (+/-)-3-methoxyestra-1,3,5(10),6,8-pentaen-17-one
  参考文献：
  名称：

  Minailova, O. N.; Rzheznikov, V. M.; Pivnitskii, K. K., Journal of general chemistry of the USSR, 1983, vol. 53, # 8, p. 1724 - 1731

  摘要：

  DOI：
• 作为产物：
  描述：

  D-17β-acetoxy-3-methoxy-14β-estra-1,3,5(10),6,8-pentaene 在 palladium on activated charcoal 氢气 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 15.0h， 生成 D-17β-acetoxy-3-methoxy-14α-estra-1,3,5(10),6,8-pentaene
  参考文献：
  名称：

  Minailova, O. N.; Rzheznikov, V. M.; Pivnitskii, K. K., Journal of general chemistry of the USSR, 1983, vol. 53, # 8, p. 1724 - 1731

  摘要：

  DOI：

文献信息

• Practical semisynthesis of equilenin and its derivatives
  作者：Tao Yue、Hong-Ping Li、Kai Ding

  DOI：10.1016/j.tetlet.2016.09.062

  日期：2016.10

  are important intermediates in the synthesis of steroidal drugs. Until now, these estrogens were produced by extraction from pregnant mare’s urine due to the lack of efficient synthetic methods. Most reported semisyntheses of equilenin involve expensive raw materials or toxic reagents to suppress undesired epimerization at C/D ring juncture. Herein, we reported a practical synthesis of highly pure

  Equilenin 2及其衍生物是甾体药物合成中的重要中间体。到目前为止，由于缺乏有效的合成方法，这些雌激素是通过从怀孕母马的尿液中提取而产生的。大多数报道的马来烯半合成涉及昂贵的原料或有毒试剂，以抑制C / D环连接处不希望的差向异构。在此，我们报道了使用常规试剂从容易获得的原料6中实际合成高纯度马鞭草蛋白及其衍生物的方法。
• Dispironaphthalenones and spironaphthalenones as novel dehydrogenation reagents
  作者：Tirumalai R. Kasturi、Jitendra A. Sattigeri

  DOI：10.1016/s0040-4020(01)88233-8

  日期：1992.1

  Dehydrogenation of a number of dihydroaromatic substrates has been carried out using either dispironaphthalenone 1 or spironaphthalenones 2 & 3 as dehydrogenating agents. The reaction is over in refluxing mesitylene in 1-2 hr and the yields of the aromatised products are fairly good (65-70%).
• Synthesis and Study of Equilenin Derivatives and Modified Analogs
  作者：E. A. Urusova、I. A. Gluzdikov、S. I. Selivanov、G. L. Starova、S. V. Nikolaev、A. G. Shavva

  DOI：10.1023/b:rujo.0000036071.26335.eb

  日期：2004.4

  Modified equilenin analogs were synthesized with a view to examine the relation between the structure and biological properties of steroid estrogens. The H-1 and C-13 NMR signals of six estra-1,3,5,7,9-pentaenes were completely assigned using homo- and heteronuclear correlation NMR spectroscopy. The structure of equilenin methyl ester was determined by X-ray analysis. Among the synthesized steroids, compounds were found which exhibit hypocholesterinemic activity with no uterotropic and hypertriglyceridemic effects.