[(1S,2S,4S,6R,7S,8R,9S,11S,12S,13S,16R,18S)-11-benzoyloxy-7,9,13-trimethyl-6-(3-methylbut-3-enyl)-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosan-16-yl] benzoate | 1266102-45-7

• 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: [(1S,2S,4S,6R,7S,8R,9S,11S,12S,13S,16R,18S)-11-benzoyloxy-7,9,13-trimethyl-6-(3-methylbut-3-enyl)-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosan-16-yl] benzoate
• CAS: 1266102-45-7
• 化学式: C₄₁H₅₂O₅
• 分子量: 624.861
• InChiKey: HHINFTMHNSYTIY-HBEXNNKHSA-N

物化性质

• 沸点：
  678.4±50.0 °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)：
  10.6
• 重原子数：
  46
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(1S,2S,4S,6R,7S,8R,9S,11S,12S,13S,16R,18S)-11-benzoyloxy-7,9,13-trimethyl-6-(3-methylbut-3-enyl)-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosan-16-yl] benzoate 在 lithium aluminium tetrahydride 、 碘苯二乙酸 、 mercury(II) diacetate 、 碘 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 21.25h， 生成 20-deshydroxy-24-desmethyl-22-epi-hippuristanol
  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：

  龙舌兰皂苷乙酯 在 吡啶 、 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 四氧化锇 、 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 氨 、 碘 、 sodium cyanoborohydride 、 calcium 、 potassium carbonate 、 溶剂黄146 、 N-甲基吗啉氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 43.0h， 生成 [(1S,2S,4S,6R,7S,8R,9S,11S,12S,13S,16R,18S)-11-benzoyloxy-7,9,13-trimethyl-6-(3-methylbut-3-enyl)-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosan-16-yl] benzoate
  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

文献信息

• Synthesis of the Antiproliferative Agent Hippuristanol and Its Analogues via Suárez Cyclizations and Hg(II)-Catalyzed Spiroketalizations
  作者：Kontham Ravindar、Maddi Sridhar Reddy、Lisa Lindqvist、Jerry Pelletier、Pierre Deslongchamps

  DOI：10.1021/jo102054r

  日期：2011.3.4

  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.