2β-Azido-3α-hydroxy-5α-androstanon-(17) | 4817-43-0

• 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: 2β-Azido-3α-hydroxy-5α-androstanon-(17)
• 英文别名: 2β-azido-3α-hydroxy-5α-androstan-17-one；(2beta,3alpha,5alpha)-2-Azido-3-hydroxyandrostan-17-one；(2S,3S,5S,8R,9S,10S,13S,14S)-2-azido-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
• CAS: 4817-43-0
• 化学式: C₁₉H₂₉N₃O₂
• 分子量: 331.458
• InChiKey: HVCPQJTYNXIKBN-PPMYXAGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  51.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-辛炔 、 2β-Azido-3α-hydroxy-5α-androstanon-(17) 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.0h， 以47%的产率得到2β-(4-hexyl-1,2,3-triazol-1-yl)-3-hydroxy-5-androstan-17-one
  参考文献：
  名称：

  Synthesis of ferrocene-labeled steroids via copper-catalyzed azide–alkyne cycloaddition. Reactivity difference between 2β-, 6β- and 16β-azido-androstanes

  摘要：

  Copper-catalyzed cycloaddition of steroidal azides and ferrocenyl-alkynes were found to be an efficient methodology for the synthesis of ferrocene-labeled steroids. At the same time, a great difference between the reactivity of 2 beta- or 16 beta-azido-androstanes and a sterically hindered 6 beta-azido steroid toward both ferrocenyl-alkynes and simple alkynes, such as phenylacetylene, 1-octyne, propargyl acetate and methyl propiolate, was observed. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.04.005
• 作为产物：
  描述：

  2α,3α-epoxy-5α-androstan-17-one 在 sodium azide 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以62%的产率得到2β-Azido-3α-hydroxy-5α-androstanon-(17)
  参考文献：
  名称：

  Synthesis of ferrocene-labeled steroids via copper-catalyzed azide–alkyne cycloaddition. Reactivity difference between 2β-, 6β- and 16β-azido-androstanes

  摘要：

  Copper-catalyzed cycloaddition of steroidal azides and ferrocenyl-alkynes were found to be an efficient methodology for the synthesis of ferrocene-labeled steroids. At the same time, a great difference between the reactivity of 2 beta- or 16 beta-azido-androstanes and a sterically hindered 6 beta-azido steroid toward both ferrocenyl-alkynes and simple alkynes, such as phenylacetylene, 1-octyne, propargyl acetate and methyl propiolate, was observed. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.04.005

文献信息

• Steroide, 28. Darstellung von Steroidhormon‐Analogen aus 2.3 β‐Imino‐5α‐androstanol‐(17β) und 3α‐Chlor‐2 β‐amino‐5α‐androstanol‐(17 β)
  作者：Kurt Ponsold、Wolfgang Preibsch

  DOI：10.1002/cber.19711040609

  日期：1971.6

  Abstract2.3β‐Imino‐5α‐androstanol‐(17β) (2a) wurde aus 2.3α‐Epoxy‐5α‐androstanon‐(17) über den entsprechenden Azidoalkoholsulfonsäureester synthetisiert und zu 3α‐Chlor‐2β‐amino‐5α‐androstanol‐(17β) (3) umgesetzt. Aus diesen beiden Verbindungen wurden Oxazoline, Thioxothiazolidine, Aminoalkohole und Aminothiole dargestellt.
• Synthesis of ferrocene-labeled steroids via copper-catalyzed azide–alkyne cycloaddition. Reactivity difference between 2β-, 6β- and 16β-azido-androstanes
  作者：Klaudia Fehér、János Balogh、Zsolt Csók、Tamás Kégl、László Kollár、Rita Skoda-Földes

  DOI：10.1016/j.steroids.2012.04.005

  日期：2012.6

  Copper-catalyzed cycloaddition of steroidal azides and ferrocenyl-alkynes were found to be an efficient methodology for the synthesis of ferrocene-labeled steroids. At the same time, a great difference between the reactivity of 2 beta- or 16 beta-azido-androstanes and a sterically hindered 6 beta-azido steroid toward both ferrocenyl-alkynes and simple alkynes, such as phenylacetylene, 1-octyne, propargyl acetate and methyl propiolate, was observed. (C) 2012 Elsevier Inc. All rights reserved.