6beta-Azido-5alpha,3beta-dihydroxyandrostan-17-one | 1380425-24-0

• 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: 6beta-Azido-5alpha,3beta-dihydroxyandrostan-17-one
• 英文别名: (3S,5R,6R,8R,9S,10R,13S,14S)-6-azido-3,5-dihydroxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 1380425-24-0
• 化学式: C₁₉H₂₉N₃O₃
• 分子量: 347.458
• InChiKey: BVPAMGSCLSFYHK-CWBKUMBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 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：
  71.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6beta-Azido-5alpha,3beta-dihydroxyandrostan-17-one 、 丙炔酸甲酯 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3β,5-dihydroxy-6β-(4-methoxycarbonyl-1,2,3-triazol-1-yl)-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：

  5,6α-epoxy-3β-hydroxy-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86%的产率得到6beta-Azido-5alpha,3beta-dihydroxyandrostan-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