3β-Acetoxy-19-norandrosta-1(10),5-dien-17-one | 73680-47-4

• 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: 3β-Acetoxy-19-norandrosta-1(10),5-dien-17-one
• 英文别名: [(3S,8R,9S,13S,14S)-13-methyl-17-oxo-3,4,7,8,9,11,12,14,15,16-decahydro-2H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 73680-47-4
• 化学式: C₂₀H₂₆O₃
• 分子量: 314.425
• InChiKey: NCPKWEZLFUIMCK-ANSOJVFESA-N

物化性质

• 熔点：
  86-92 °C(Solv: methanol (67-56-1))
• 沸点：
  459.9±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3β-Acetoxy-19-norandrosta-1(10),5-dien-17-one 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 19.5h， 生成 5α,10α-estrane-3,17-dione
  参考文献：
  名称：

  Suginome, Hiroshi; Senboku, Hisanori; Yamada, Shinji, Journal of the Chemical Society. Perkin transactions I, 1990, # 8, p. 2199 - 2205

  摘要：

  DOI：
• 作为产物：
  描述：

  5-Bromo-3β,19-dihydroxy-6β,19-epoxy-5α-androstan-17-one 在 碘 、 溶剂黄146 、 mercury(II) oxide 、 锌 作用下， 生成 3β-Acetoxy-19-norandrosta-1(10),5-dien-17-one
  参考文献：
  名称：

  Suginome, Hiroshi; Senboku, Hisanori; Yamada, Shinji, Journal of the Chemical Society. Perkin transactions I, 1990, # 8, p. 2199 - 2205

  摘要：

  DOI：

文献信息

• 19-Hydroxy-steroids. Part 7. Boron trifluoride-catalysed reactions of 19-hydroxy- and 19-acetoxy-5,6-epoxy-steroids
  作者：Harold Mastalerz、Peter Morand

  DOI：10.1039/p19810000154

  日期：——

  The effects of strong electron-withdrawing substituents at C-19 upon the boron trifluoride-catalysed reactions of 5,6-epoxy-steroids were examined. 3β-Acetoxy-5,6β-epoxy-5β-cholestan-19-ol (4) and 3β-acetoxy-5,6β-epoxy-19-hydroxy-5β-androstan-17-one (2) reacted with boron trifluoride gas in benzene with the loss of the C-10 groups as formaldehyde and subsequent dehydration to give the 1(10),5-dienes (16)

  考察了C-19上强吸电子取代基对三氟化硼催化的5，6-环氧-甾类化合物反应的影响。与三氟化硼气体反应的3β-乙酰氧基-5,6β-环氧-5β-胆甾醇19-醇（4）和3β-乙酰氧基-5,6β-环氧-19-羟基-5β-雄甾烷17-一（2）苯中的C-10基团以甲醛的形式损失，随后脱水，分别得到1（10），5-二烯（16）和（17）。3β，19-二乙酰氧基5,6β环氧5β-胆甾烷（5）和3β，19-二乙酰氧基5,6β环氧5β雄甾烷-17-酮（3），得到作为唯一的重排产物的乙-也不是5β-甲酰基类固醇（26）和（25）。3β-乙酰氧基-5,6α-环氧-5α-胆甾醇-19-醇（12）和其19-乙酸酯衍生物（13）给出了由于19-官能团参与环氧化物开口而产生的产物。
• Stereoelectronically Controlled, Thallium(III)-Mediated C-19 Degradation of 19-Hydroxy Steroids. An Expedient Route to Estrone and its Congeners via 19-Nor-10.beta.-hydroxy Intermediates
  作者：Pavel Kocovsky、Richard S. Baines

  DOI：10.1021/jo00097a056

  日期：1994.9

  Estrone- (8b) has been synthesized in four steps from 3 beta-acetoxy-19-hydroxyandrost-5-en-17-one (2b), readily available from an industrial precursor. A key feature of the strategy is a stereoelectronically controlled, TI(III)-mediated degradation (2b --> 5b). Oppenauer oxidation of diol 6b, resulting from saponification of the acetate 5b, afforded the unsaturated 10 beta-hydroxy ketone 7b, acid treatment of which induced aromatization affording 8b. An alternative route including dehydration (5b --> 9b) followed by Oppenauer oxidation (10b --> 8b) gave comparable results. This strategy has first been developed with the aid of cholestane model compounds (2a --> 5a) and then successfully applied to the synthesis of analogues in the cholestane, androstane, and pregnane series to produce the corresponding 19-nor-10 beta-hydroxy derivatives 7a-d and A-aromatic steroids 8a-d.
• SUGINOME, HIROSHI;SENBOKU, HISANORI;YAMADA, SHINJI, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 2199-2205
  作者：SUGINOME, HIROSHI、SENBOKU, HISANORI、YAMADA, SHINJI

  DOI：——

  日期：——
• SUGINOME, HIROSHI;SENBOKU, HISANORI;YAMADA, SHINJI, TETRAHEDRON LETT., 29,(1988) N 1, 79-80
  作者：SUGINOME, HIROSHI、SENBOKU, HISANORI、YAMADA, SHINJI

  DOI：——

  日期：——