17-epi-17-fluoro-17-deoxytestosterone

• 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: 17-epi-17-fluoro-17-deoxytestosterone
• 英文别名: (8R,9S,10R,13S,14S,17R)-17-fluoro-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• 化学式: C₁₉H₂₇FO
• 分子量: 290.421
• InChiKey: KTXFGWYVPQLTKZ-KZYORJDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  睾酮 在 1,3-bis(2,6-diisopropylphenyl)-2-fluoroimidazolium tetrafluoroborate 、 cesium fluoride 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以79%的产率得到17-epi-17-fluoro-17-deoxytestosterone
  参考文献：
  名称：

  AlkylFluor: Deoxyfluorination of Alcohols

  摘要：

  A practical, high-yielding method for the deoxy-fluorination of alcohols is presented using AlkylFluor, a novel salt analogue of PhenoFluor. AlkylFluor is readily prepared on multigram scale and is stable to long-term storage in air and exposure to water. The practicality and applicability of this method is demonstrated with a variety of primary and secondary alcohol substrates.

  DOI：

  10.1021/acs.orglett.6b03086

文献信息

• Late-Stage Deoxyfluorination of Alcohols with PhenoFluor
  作者：Filippo Sladojevich、Sophie I. Arlow、Pingping Tang、Tobias Ritter

  DOI：10.1021/ja3125405

  日期：2013.2.20

  An operationally simple protocol for the selective deoxyfluorination of structurally complex alcohols is presented. Several fluorinated derivatives of natural products and pharmaceuticals have been prepared to showcase the potential of the method for late-stage diversification and its functional group compatibility. A series of simple guidelines for predicting the selectivity in substrates with multiple alcohols is given.
• Steroids. CCXL.^1,2 The Reaction of Steroidal Alcohols with 2-Chloro-1,1,2-trifluorotriethylamine
  作者：Lawrence H. Knox、Esperanza Velarde、Sarah Berger、Dolores Cuadriello、Alexander D. Cross

  DOI：10.1021/jo01031a019

  日期：1964.8