17β-triflate-5α-androstan-3,6-dione | 257619-87-7

• 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-triflate-5α-androstan-3,6-dione
• 英文别名: [(5S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3,6-dioxo-2,4,5,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] trifluoromethanesulfonate
• CAS: 257619-87-7
• 化学式: C₂₀H₂₇F₃O₅S
• 分子量: 436.493
• InChiKey: CXLLJZRXAYHKLI-YDOJUKJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  17β-triflate-5α-androstan-3,6-dione 在 lithium carbonate 、 potassium tri-sec-butyl-borohydride 、 N,N-二异丙基乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.08h， 生成 17α-bromo-3α-(triphenylsilyloxy)-5α-androstan-6-one
  参考文献：
  名称：

  Long-Range Through-Bond Photoactivated σ Bond Cleavage in Steroids. Intramolecular Sensitized Debromination¹

  摘要：

  [GRAPHICS]The photolysis of 17 alpha-bromo-3 alpha-(triphenylsilyloxy)-5 alpha-androstane (2; 3 alpha TPSO/17 alpha Br) and 17 alpha-bromo-3 alpha-(triphenylsilyloxy)-5 alpha-androstan-6- one (3; 3 alpha TPSO/6ketone/17 alpha Br) is described. Irradiation of 2 with 266 nm light leads to debromination via intramolecular transfer of triplet excitation energy with a quantum efficiency of 0.0011, Photolysis of 3 with both 266 and 308 nm light leads to debromination with quantum efficiencies of ca. 0.0066, The debromination of 3 is attributed to activation via the ketone excited singlet state, with singlet energy transfer from C6 to C17 ca, 35% efficient and occurring with a rate constant of 1.4 x 10(8) s(-1).

  DOI：

  10.1021/ol990319s
• 作为产物：
  描述：

  三氟甲磺酸酐 、 17b-羟基-5a-雄甾烷-3,6-二酮 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以98%的产率得到17β-triflate-5α-androstan-3,6-dione
  参考文献：
  名称：

  Long-Range Through-Bond Photoactivated σ Bond Cleavage in Steroids. Intramolecular Sensitized Debromination¹

  摘要：

  [GRAPHICS]The photolysis of 17 alpha-bromo-3 alpha-(triphenylsilyloxy)-5 alpha-androstane (2; 3 alpha TPSO/17 alpha Br) and 17 alpha-bromo-3 alpha-(triphenylsilyloxy)-5 alpha-androstan-6- one (3; 3 alpha TPSO/6ketone/17 alpha Br) is described. Irradiation of 2 with 266 nm light leads to debromination via intramolecular transfer of triplet excitation energy with a quantum efficiency of 0.0011, Photolysis of 3 with both 266 and 308 nm light leads to debromination with quantum efficiencies of ca. 0.0066, The debromination of 3 is attributed to activation via the ketone excited singlet state, with singlet energy transfer from C6 to C17 ca, 35% efficient and occurring with a rate constant of 1.4 x 10(8) s(-1).

  DOI：

  10.1021/ol990319s