1,4-bis[3β-[(tert-butyldimethylsilyl)oxy]-17β-hydroxy-5α-androstan-17α-yl-ethynyl]benzene | 1404499-80-4

• 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: 1,4-bis[3β-[(tert-butyldimethylsilyl)oxy]-17β-hydroxy-5α-androstan-17α-yl-ethynyl]benzene
• 英文别名: (3S,5S,8R,9S,10S,13S,14S,17S)-3-[tert-butyl(dimethyl)silyl]oxy-17-[2-[4-[2-[(3S,5S,8R,9S,10S,13S,14S,17S)-3-[tert-butyl(dimethyl)silyl]oxy-17-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethynyl]phenyl]ethynyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-ol
• CAS: 1404499-80-4
• 化学式: C₆₀H₉₄O₄Si₂
• 分子量: 935.575
• InChiKey: QHSWKKHWASJGIQ-FTGYIRRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.72
• 重原子数：
  66
• 可旋转键数：
  10
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-bis[3β-[(tert-butyldimethylsilyl)oxy]-17β-hydroxy-5α-androstan-17α-yl-ethynyl]benzene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以97%的产率得到1,4-bis(3β,17β-dihydroxy-5α-androstan-17α-yl-ethynyl)benzene
  参考文献：
  名称：

  Macrocyclic Molecular Rotors with Bridged Steroidal Frameworks

  摘要：

  In this work, we describe the synthesis and solid-state dynamics of isomeric molecular rotors 7E and 7Z, consisting of two androstane steroidal frameworks linked by the D rings by triple bonds at their C17 positions to a 1,4-phenylene rotator. They are also linked by the A rings by an alkenyl diester bridge to restrict the conformational flexibility of the molecules and reduce the number of potential crystalline arrays. The analysis of the resulting molecular structures and packing motifs offered insights of the internal dynamics that were later elucidated by means of line shape analyses of the spectral features obtained through variable-temperature solid-state C-13 NMR; such analysis revealed rotations in the solid state occurring at kilohertz frequency at room temperature.

  DOI：

  10.1021/jo3020402
• 作为产物：
  描述：

  (3S,10S,13S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta-[a]phenanthren-17-one 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 23.17h， 生成 1,4-bis[3β-[(tert-butyldimethylsilyl)oxy]-17β-hydroxy-5α-androstan-17α-yl-ethynyl]benzene
  参考文献：
  名称：

  Macrocyclic Molecular Rotors with Bridged Steroidal Frameworks

  摘要：

  In this work, we describe the synthesis and solid-state dynamics of isomeric molecular rotors 7E and 7Z, consisting of two androstane steroidal frameworks linked by the D rings by triple bonds at their C17 positions to a 1,4-phenylene rotator. They are also linked by the A rings by an alkenyl diester bridge to restrict the conformational flexibility of the molecules and reduce the number of potential crystalline arrays. The analysis of the resulting molecular structures and packing motifs offered insights of the internal dynamics that were later elucidated by means of line shape analyses of the spectral features obtained through variable-temperature solid-state C-13 NMR; such analysis revealed rotations in the solid state occurring at kilohertz frequency at room temperature.

  DOI：

  10.1021/jo3020402