5α-hydroxyandrostane-6,17-dione | 15296-65-8

• 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-hydroxyandrostane-6,17-dione
• 英文别名: 5-hydroxy-5α-androstanedione-(6.17)；5-Hydroxy-5α-androstandion-(6.17)；(5R,8R,9S,10R,13S,14S)-5-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-6,17-dione
• CAS: 15296-65-8
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: IMNXJWBPNQLVIH-WERNOVKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  5α-hydroxyandrostane-6,17-dione 在 乙酸酐 作用下， 生成 5-acetoxy-5α-androstanedione-(6.17)
  参考文献：
  名称：

  ÜberSteroide和性激素。（65.米特隆）。Herstellung des Δ4-Androsten-6、17维

  摘要：

  DOI：

  10.1002/hlca.194002301178
• 作为产物：
  描述：

  5α,6α-epoxyandrostan-17-one 在 potassium permanganate 、 iron(III) perchlorate 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 20.0h， 以78%的产率得到5α-hydroxyandrostane-6,17-dione
  参考文献：
  名称：

  One-pot, high yield synthesis of α-ketols from Δ5-steroids

  摘要：

  a-Hydroxy ketones (alpha-ketols) are present in many compounds with biological activity. Several methods are available for the preparation of alpha-ketols but only a few of them describe the synthesis of steroid alpha-ketols from olefins. In this work, a new system consisting of KMnO4/Fe(ClO4)(3)center dot nH(2)O was used in order to achieve the direct conversion of Delta(5)-steroids to their corresponding alpha-ketols, in high yields. Consideration of the probable reaction mechanism is provided. 2D homo- and heteronuclear correlation NMR spectroscopic techniques were used to assign H-1 and C-13 resonances of some synthesized compounds. This method has potential for the preparation of alpha-hydroxy ketones of biological interest. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.11.002

文献信息

• Hanson, James R.; Kiran, Ismail, Journal of Chemical Research, Miniprint, 1999, # 12, p. 2933 - 2944
  作者：Hanson, James R.、Kiran, Ismail

  DOI：——

  日期：——
• 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
  作者：Mitsuteru Numazawa、Keiko Yamada

  DOI：10.1016/s0039-128x(97)00136-0

  日期：1998.2

  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.
• Hanson, James R.; Truneh, Almaz, Journal of the Chemical Society. Perkin transactions I, 1988, p. 2001 - 2004
  作者：Hanson, James R.、Truneh, Almaz

  DOI：——

  日期：——