2α,17β-Diacetoxy-5α-androstan-3-one | 14026-24-5

• 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: 2α,17β-Diacetoxy-5α-androstan-3-one
• 英文别名: 2α,17β-Dihydroxyandrostan-3-one diacetate；2α,17β-diacetoxy-(5α)-androstan-3-one；5α-Androstan-2α,17β-diol-3-on-diacetat；[(2R,5S,8R,9S,10S,13S,14S,17S)-2-acetyloxy-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 14026-24-5
• 化学式: C₂₃H₃₄O₅
• 分子量: 390.52
• InChiKey: HWAOMBULLIBDHL-FEQOUAIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2α,17β-Diacetoxy-5α-androstan-3-one 在 ammonium acetate 、 potassium hydrogencarbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 17β-Hydroxy-2'-methyl-oxazolo<5'.4'-2.3>androsten
  参考文献：
  名称：

  Ohta,G. et al., Chemical and pharmaceutical bulletin, 1968, vol. 16, # 8, p. 1487 - 1497

  摘要：

  DOI：
• 作为产物：
  描述：

  2α,3α-Epoxyandrostane-3β,17β-diol acetate 在 氢溴酸 作用下， 以 吡啶 、 溶剂黄146 、 甲苯 为溶剂， 反应 48.0h， 生成 2α,17β-Diacetoxy-5α-androstan-3-one
  参考文献：
  名称：

  Synthesis and Biological Activity Of Unsymmetrical Bis-Steroidal Pyrazines Related to the Cytotoxic Marine Natural Product Cephalostatin 1

  摘要：

  A mild, high-yielding synthesis of symmetrical steroidal pyrazines was achieved from the dimerization of 2-amino-3-ketosteroids, which were produced in situ from the triphenylphosphine-water reduction of the corresponding alpha-azido ketone. 2-Azidocholestan-3-one gave the dimeric steroidal pyrazine very cleanly, and two known dimeric pyrazines based on androstanone were also made using this methodology. Both C-2-symmetric geometric isomers of the dimeric steroidal pyrazine derived from cholestane were prepared by reaction of 2,3-diaminocholestane with cholestane-2,3-dione. A route to unsymmetrical bis-steroidal pyrazines was based on the observation that alpha-acetoxy ketones react with alpha-amino oximes directly with no need for oxidation of intermediate dihydropyrazines. Heating either 2 beta,17 beta-dihydroxyandrostan-3-one diacetate or 2 beta,17 beta-dihydroxyhecogenin-3-one diacetate with 2-amino-3-methoxyiminocholestane in toluene at 145 degrees C gave the corresponding unsymmetrical pyrazine in moderate yield. Five of the steroidal pyrazines were evaluated in the National Cancer Institute's new in vitro, disease-oriented antitumor screen, but none showed sufficient activity to warrant in vivo investigation.

  DOI：

  10.1021/jo00101a052