17α-bromo-3α-(triphenylsilyloxy)-5α-androstane | 257619-76-4

• 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: 17α-bromo-3α-(triphenylsilyloxy)-5α-androstane
• 英文别名: [(3R,5S,8R,9S,10S,13S,14S,17R)-17-bromo-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy-triphenylsilane
• CAS: 257619-76-4
• 化学式: C₃₇H₄₅BrOSi
• 分子量: 613.753
• InChiKey: NOEPMYRIOXIAMF-LVQNTUPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  17α-bromo-3α-(triphenylsilyloxy)-5α-androstane 在 ammonium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 3α-(triphenylsilyloxy)-5α-androstane
  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：

  雄诺龙 在 吡啶 、 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 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.33h， 生成 17α-bromo-3α-(triphenylsilyloxy)-5α-androstane
  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

文献信息

• Long-Range Through-Bond Photoactivated σ Bond Cleavage in Steroids. Intramolecular Sensitized Debromination¹
  作者：Wen-Shan Li、Harry Morrison

  DOI：10.1021/ol990319s

  日期：2000.1.1

  [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).