5α,6β-dihydroxy-19-acetoxyandrost-17-one | 204330-83-6

• 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: 5α,6β-dihydroxy-19-acetoxyandrost-17-one
• 英文别名: [(5R,6R,8R,9S,10R,13S,14S)-5,6-dihydroxy-13-methyl-17-oxo-2,3,4,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-10-yl]methyl acetate
• CAS: 204330-83-6
• 化学式: C₂₁H₃₂O₅
• 分子量: 364.482
• InChiKey: CQGHCKFUUKPDSZ-VWUMJDOOSA-N

物化性质

• 沸点：
  481.9±45.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5α,6β-dihydroxy-19-acetoxyandrost-17-one 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 1.8h， 以87%的产率得到5α-hydroxy-19-acetoxyandrosta-6,17-dione
  参考文献：
  名称：

  Reaction of androst-5-en-17-one with hypobromous acid and its use for synthesis of 19-oxygenated 5-ene and 4-en-6-one steroids

  摘要：

  Reaction of androst-5-en-17-one (1) with hypobromous acid using a short reaction rime (30 min) along with a careful isolation procedure gave, for the first time, the addition 5 alpha-bromo-6 beta-hydroxyandrostan-17-one (3), in 43% yield. This bromohydrin was much more reactive than 5 alpha-brormo-3 beta-acetoxy-6 beta-hydroxyandrostan-17-one (4) towards KHCO3 and HClO4. The high reactivity of compound 3 was found ro be a principal reason for the difficulty in isolating this compound the addition reaction so far. 19-Hydroxyandrost-5-en-17-one (16) and androst-5-ene-17,19-dione (18), ns well ns 19-hydroxyandrost-4-ene-6,17-dione (28) and androst-4-ene-6,17,19-trione (29), were synthesised through hypoiodite reaction of the bromohydrin 3 as a key reaction. (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00136-0
• 作为产物：
  描述：

  19-acetoxy-5,6-epoxyandrost-17-one 在 高氯酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 15.0h， 以45%的产率得到5β,6α-dihydroxy-19-acetoxyandrost-17-one
  参考文献：
  名称：

  Reaction of androst-5-en-17-one with hypobromous acid and its use for synthesis of 19-oxygenated 5-ene and 4-en-6-one steroids

  摘要：

  Reaction of androst-5-en-17-one (1) with hypobromous acid using a short reaction rime (30 min) along with a careful isolation procedure gave, for the first time, the addition 5 alpha-bromo-6 beta-hydroxyandrostan-17-one (3), in 43% yield. This bromohydrin was much more reactive than 5 alpha-brormo-3 beta-acetoxy-6 beta-hydroxyandrostan-17-one (4) towards KHCO3 and HClO4. The high reactivity of compound 3 was found ro be a principal reason for the difficulty in isolating this compound the addition reaction so far. 19-Hydroxyandrost-5-en-17-one (16) and androst-5-ene-17,19-dione (18), ns well ns 19-hydroxyandrost-4-ene-6,17-dione (28) and androst-4-ene-6,17,19-trione (29), were synthesised through hypoiodite reaction of the bromohydrin 3 as a key reaction. (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00136-0

文献信息

• Role of Hydrophilic Interaction in Binding of Hydroxylated 3-Deoxy C₁₉ Steroids to the Active Site of Aromatase
  作者：Mitsuteru Numazawa、Keiko Yamada、Syoko Nitta、Chika Sasaki、Kanae Kidokoro

  DOI：10.1021/jm010282t

  日期：2001.11.1

  relationship of a novel class of aromatase inhibitors, C(19) steroids having no oxygen function at C-3, we tested aromatase inhibition activity of polar diol compounds 4,19-dihydroxyandrost-5-en-17-ones (25 and 27) and 6,19-dihydroxyandrost-4-en-17-ones (36 and 37). 4alpha,19-Diol 25 was synthesized from tert-butyldimethylsilyoxyandrost-4-ene steroid (9) through its OsO(4) oxidation, giving the 4alpha,5alpha-dihydroxy

  作为我们对一类新型芳香酶抑制剂C（19）类固醇在C-3处无氧功能的构效关系的研究的一部分，我们测试了极性二醇化合物4,19-dihydroxyandrost-5-的芳香酶抑制活性en-17-ones（25和27）和6,19-dihydroxyandrost-4-en-17-ones（36和37）。由叔丁基二甲基甲硅烷氧基雄烷-4-烯类固醇（9）通过其OsO（4）氧化合成4alpha，19-Diol 25，得到4alpha，5alpha-dihydroxy衍生物12作为关键反应。乙酰化5beta，6alpha-dihydroxy-19-acetate 30及其5alpha，6beta-analogue 31，然后用SOCl（2）脱水和碱性羟基化分别得到6alpha，19-二醇36和6beta-异构体37。化合物（25）的C-4处的羟基的立体化学和化合物36和37的C-6处的羟基的立体化学分别基于（1）H