(4aS,4bR,8R,8aR,10aR)-8-(tert-butyldimethylsilyloxy)-4a-[(tert-butyldimethylsilyloxy)methyl]-1,1,8a-trimethyl-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-2(1H)-one | 1402170-98-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (4aS,4bR,8R,8aR,10aR)-8-(tert-butyldimethylsilyloxy)-4a-[(tert-butyldimethylsilyloxy)methyl]-1,1,8a-trimethyl-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-2(1H)-one
• CAS: 1402170-98-2
• 化学式: C₃₀H₅₈O₃Si₂
• 分子量: 522.96
• InChiKey: FKASRQAWYINTDC-OEBFQYBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.99
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4aS,4bR,8R,8aR,10aR)-8-(tert-butyldimethylsilyloxy)-4a-[(tert-butyldimethylsilyloxy)methyl]-1,1,8a-trimethyl-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-2(1H)-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以89%的产率得到(3S,4aR,6aR,7R,10aR,10bS)-3,10b-ethano-4,4,6a-trimethyl-3,4,4a,5,6,6a,7,8,9,10,10a,10b-dodecahydro-1H-naphto[1,2-c]pyran-3,7-diol
  参考文献：
  名称：

  First synthesis of decaturin C, an antiinsectant diterpenoid isolated from Penicillium thiersii

  摘要：

  The first synthesis of (+)-decaturin C, an antiinsectant diterpenoid isolated from Penicillium thiersii, was accomplished by starting from (R)-(-)-Wieland-Miescher ketone, in which our original spiro-cyclization reaction was featured as a key step. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.067
• 作为产物：
  描述：

  methyl (4aS,4bS,8R,8aR)-8-(tert-butyldimethylsilyloxy)-1,8a-dimethyl-2-oxo-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthrene-4a-carboxylate 在 咪唑 、 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 氨 、 lithium 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4aS,4bR,8R,8aR,10aR)-8-(tert-butyldimethylsilyloxy)-4a-[(tert-butyldimethylsilyloxy)methyl]-1,1,8a-trimethyl-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-2(1H)-one
  参考文献：
  名称：

  First synthesis of decaturin C, an antiinsectant diterpenoid isolated from Penicillium thiersii

  摘要：

  The first synthesis of (+)-decaturin C, an antiinsectant diterpenoid isolated from Penicillium thiersii, was accomplished by starting from (R)-(-)-Wieland-Miescher ketone, in which our original spiro-cyclization reaction was featured as a key step. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.067