[(3R,5S,8S,9S,10S,11S,13S,14S,16S,17R)-17-acetyl-10,13-dimethyl-3,11-bis(phenylmethoxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl] (4R)-5-acetyloxy-4-methylpentanoate | 1246949-33-6

• 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: [(3R,5S,8S,9S,10S,11S,13S,14S,16S,17R)-17-acetyl-10,13-dimethyl-3,11-bis(phenylmethoxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl] (4R)-5-acetyloxy-4-methylpentanoate
• CAS: 1246949-33-6
• 化学式: C₄₃H₅₈O₇
• 分子量: 686.929
• InChiKey: QOMSUDBPXUVFHU-JXFBVWQBSA-N

物化性质

• 沸点：
  722.5±60.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(3R,5S,8S,9S,10S,11S,13S,14S,16S,17R)-17-acetyl-10,13-dimethyl-3,11-bis(phenylmethoxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl] (4R)-5-acetyloxy-4-methylpentanoate 在 sodium periodate 、 四氧化锇 、 正丁基锂 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 为溶剂， 反应 15.75h， 生成 (3R,5S,8S,9S,10S,11S,13S,14S,16S,17R)-17-[(2R,5S)-2-hydroxy-5,6-dimethyl-6-(oxan-2-yloxy)hept-3-yn-2-yl]-10,13-dimethyl-3,11-bis(phenylmethoxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-ol
  参考文献：
  名称：

  Synthesis of the Antiproliferative Agent Hippuristanol and Its Analogues via Suárez Cyclizations and Hg(II)-Catalyzed Spiroketalizations

  摘要：

  A full account of the synthesis of hippuristanol and its analogues is described. Hecogenin acetate was identified as a suitable and economical starting material for this work, and substrate-controlled stereo-selection was obtained throughout the construction of the key spiroketal unit. Suarez cyclization was first used, but Hg(II)-catalyzed spiroketalization of the 3-alkyne-1,7-diol motif was finally identified as the most convenient strategy.

  DOI：

  10.1021/jo102054r
• 作为产物：
  描述：

  [(1S,2S,4S,5'R,6R,7S,8R,9S,11S,12S,13S,16R,18S)-11-benzoyloxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl] benzoate 在 chromium(VI) oxide 、 三氟化硼乙醚 、 sodium acetate 、 吡啶盐酸盐 、 乙酸酐 、 sodium hydride 、 一水合肼 、 溶剂黄146 、 potassium hydroxide 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 乙二醇 、 mineral oil 为溶剂， 反应 5.67h， 生成 [(3R,5S,8S,9S,10S,11S,13S,14S,16S,17R)-17-acetyl-10,13-dimethyl-3,11-bis(phenylmethoxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl] (4R)-5-acetyloxy-4-methylpentanoate
  参考文献：
  名称：

  Synthesis of the Antiproliferative Agent Hippuristanol and Its Analogues via Suárez Cyclizations and Hg(II)-Catalyzed Spiroketalizations

  摘要：

  A full account of the synthesis of hippuristanol and its analogues is described. Hecogenin acetate was identified as a suitable and economical starting material for this work, and substrate-controlled stereo-selection was obtained throughout the construction of the key spiroketal unit. Suarez cyclization was first used, but Hg(II)-catalyzed spiroketalization of the 3-alkyne-1,7-diol motif was finally identified as the most convenient strategy.

  DOI：

  10.1021/jo102054r