17β-hydroxy-5α-androstan-3-one diphenyl phosphate

• 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: 17β-hydroxy-5α-androstan-3-one diphenyl phosphate
• 英文别名: [(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl] diphenyl phosphate
• 化学式: C₃₁H₃₉O₅P
• 分子量: 522.621
• InChiKey: KREVWTOITIDWGI-FKVQNEAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氯磷酸二苯酯 在 正丁基锂 、 N,N-双(苯基亚甲基)-1,2-乙二胺 、 copper(II) bis(trifluoromethanesulfonate) 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 17β-hydroxy-5α-androstan-3-one diphenyl phosphate
  参考文献：
  名称：

  Phosphorylation of Alcohols with N-Phosphoryl Oxazolidinones Employing Copper(II) Triflate Catalysis

  摘要：

  Phosphoryl transfer from N-phosphoryl 5,5-diphenyl oxazolidinone is efficiently catalyzed by copper(II) triflate. The utility of this method has been demonstrated in the phosphorylation of representative primary, secondary, tertiary, phenolic, and allylic alcohols. These reaction conditions are significantly milder than employing alkoxides and allow the phosphorylation of biologically relevant molecules.

  DOI：

  10.1021/ol051104n

文献信息

• An Improved Method for Lewis Acid Catalyzed Phosphoryl Transfer with Ti(<i>t</i>-BuO)₄
  作者：Simon Jones、Dimitrios Selitsianos、Kate J. Thompson、Steven M. Toms

  DOI：10.1021/jo034331g

  日期：2003.6.1

  Several inorganic esters have been evaluated as phosphoryl transfer catalysts. Of these, Ti(t-BuO)(4) was found to be the most effective catalyst giving excellent yields of the desired phosphate esters. The loading of the catalyst could be reduced to a little as 5 mol % for a majority of substrates with no loss in the yield of product. This methodology is significantly more versatile than using TiCl4 and is suitable for the phosphorylation of more complex carbohydrates and molecules of biological interest.
• Phosphorylation of Alcohols with <i>N</i>-Phosphoryl Oxazolidinones Employing Copper(II) Triflate Catalysis
  作者：Simon Jones、Chaiwat Smanmoo

  DOI：10.1021/ol051104n

  日期：2005.7.1

  Phosphoryl transfer from N-phosphoryl 5,5-diphenyl oxazolidinone is efficiently catalyzed by copper(II) triflate. The utility of this method has been demonstrated in the phosphorylation of representative primary, secondary, tertiary, phenolic, and allylic alcohols. These reaction conditions are significantly milder than employing alkoxides and allow the phosphorylation of biologically relevant molecules.