(8R,9S,13S,14S,17S)-17-[2-[4-[2-[(8R,9S,13S,14S,17S)-17-hydroxy-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]ethynyl]-1-bicyclo[2.2.2]octanyl]ethynyl]-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol | 1446175-31-0

• 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: (8R,9S,13S,14S,17S)-17-[2-[4-[2-[(8R,9S,13S,14S,17S)-17-hydroxy-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]ethynyl]-1-bicyclo[2.2.2]octanyl]ethynyl]-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
• CAS: 1446175-31-0
• 化学式: C₅₀H₆₂O₄
• 分子量: 727.04
• InChiKey: WXBFPEFRFAOFKR-OCDXPWFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  54
• 可旋转键数：
  6
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  双环[2.2.2]辛烷-1,4-二甲醛 在 正丁基锂 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (8R,9S,13S,14S,17S)-17-[2-[4-[2-[(8R,9S,13S,14S,17S)-17-hydroxy-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]ethynyl]-1-bicyclo[2.2.2]octanyl]ethynyl]-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
  参考文献：
  名称：

  Amphidynamic Crystals of a Steroidal Bicyclo[2.2.2]octane Rotor: A High Symmetry Group That Rotates Faster than Smaller Methyl and Methoxy Groups

  摘要：

  The synthesis, crystallization, single crystal X-ray structure, and solid state dynamics of molecular rotor 3 provided with a high symmetry order and relatively cylindrical bicyclo[2.2.2]octane (BCO) rotator linked to mestranol fragments were investigated in this work. By use of solid state C-13 NMR, three rotating fragments were identified within the molecule: the BCO, the C19 methoxy and the C18 methyl groups. To determine the dynamics of the BCO group in crystals of 3 by variable temperature H-1 spin-lattice relaxation (VT H-1 T-1), we determined the H-1 T-1 contributions from the methoxy-deuterated isotopologue rotor 3-d(6). The contributions from the quaternary methyl group C18 were estimated by considering the differences between the VT H-1 T-1 of mestranol 8 and methoxy-deuterated mestranol 8-d(3). From these studies it was determined that the BCO rotator in 3 has an activation energy of only 1.15 kcal mol(-1), with a barrier for site exchange that is smaller than those of methyl (E-a = 1.35 kcal mol(-1)) and methoxy groups (E-a = 1.92 kcal mol(-1)), despite their smaller moments of inertia and surface areas.

  DOI：

  10.1021/ja4024463