(5S,6S)-6-[(R,2E,6E)-1-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-2,6-dimethylocta-2,6-dien-1-yl]-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone | 1207478-02-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5S,6S)-6-[(R,2E,6E)-1-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-2,6-dimethylocta-2,6-dien-1-yl]-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone
• CAS: 1207478-02-1
• 化学式: C₂₆H₄₄O₃Si
• 分子量: 432.719
• InChiKey: ZXPGWYQVADZTEE-IQBLQUEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.77
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5S,6S)-6-[(R,2E,6E)-1-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-2,6-dimethylocta-2,6-dien-1-yl]-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone 、 氯磷酸二乙酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以95%的产率得到(R,2E,6E)-8-[(tert-butyldimethylsilyl)oxy]-3,7-dimethyl-8-[(1S,6S)-3-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-en-1-yl]octa-2,6-dien-1-yl diethyl phosphate
  参考文献：
  名称：

  Enantiospecific Synthesis of the Cubitane Skeleton

  摘要：

  The fully substituted 12-membered macrocycle of the cubitane-type diterpenoids has been assembled in an enantioselective manner following a novel "bridge-and-cut" strategy. Hydroxyalkylation of (S)-carvone afforded a carvonylgeraniol, which underwent transannular cyclization on treatment with samarium diiodide in THE Fragmentation of one of the shorter bridges of the resulting [8.2.2]bicycle liberated the 12-membered ring with the desired cis-arrangement of the isopropenyl side chains.

  DOI：

  10.1021/ol902854t
• 作为产物：
  描述：

  (R,2E,6E)-8-[(tert-butyldimethylsilyl)oxy]-3,7-dimethyl-8-[(1S,6S)-3-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-en-1-yl]octa-2,6-dien-1-yl acetate 在 lithium hydroxide monohydrate 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 120.0h， 以90%的产率得到(5S,6S)-6-[(R,2E,6E)-1-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-2,6-dimethylocta-2,6-dien-1-yl]-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone
  参考文献：
  名称：

  Enantiospecific Synthesis of the Cubitane Skeleton

  摘要：

  The fully substituted 12-membered macrocycle of the cubitane-type diterpenoids has been assembled in an enantioselective manner following a novel "bridge-and-cut" strategy. Hydroxyalkylation of (S)-carvone afforded a carvonylgeraniol, which underwent transannular cyclization on treatment with samarium diiodide in THE Fragmentation of one of the shorter bridges of the resulting [8.2.2]bicycle liberated the 12-membered ring with the desired cis-arrangement of the isopropenyl side chains.

  DOI：

  10.1021/ol902854t