(1'R,2S,3aS,4'R,6aS)-1',7',7'-trimethyl-6-[(E)-oct-1-enyl]spiro[3a,6a-dihydrocyclopenta[d][1,3]dioxole-2,2'-bicyclo[2.2.1]heptane]-4-one | 1268607-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (1'R,2S,3aS,4'R,6aS)-1',7',7'-trimethyl-6-[(E)-oct-1-enyl]spiro[3a,6a-dihydrocyclopenta[d][1,3]dioxole-2,2'-bicyclo[2.2.1]heptane]-4-one
• CAS: 1268607-16-4
• 化学式: C₂₃H₃₄O₃
• 分子量: 358.521
• InChiKey: UWOCWFJDIMAGHV-NHHXPDRESA-N

物化性质

• 沸点：
  471.0±45.0 °C(predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1'R,2S,3aS,4'R,6aS)-1',7',7'-trimethyl-6-[(E)-oct-1-enyl]spiro[3a,6a-dihydrocyclopenta[d][1,3]dioxole-2,2'-bicyclo[2.2.1]heptane]-4-one 在 10% palladium on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以88%的产率得到(1'R,2S,3aS,4'R,6S,6aS)-1',7',7'-trimethyl-6-octylspiro[3a,5,6,6a-tetrahydrocyclopenta[d][1,3]dioxole-2,2'-bicyclo[2.2.1]heptane]-4-one
  参考文献：
  名称：

  Stereocontrolled synthesis of enantiopure anticancer cyclopentenone prostaglandin analogues: (−)- and (+)-TEI-9826

  摘要：

  The synthesis of both enantiomers of TEI-9826 has been accomplished in seven steps with an overall yield of 44% starting from diastereomeric camphor protected 3-[(dimethoxyphosphoryl)methyl]-4,5-dihydroxycyclopent-2-enones. The key steps include a fully diastereoselective hydrogenation of the endocyclic carbon-carbon double bond in the cyclopentenone ring controlled with a chiral diol moiety and the conversion of the latter into a new transposed olefinic bond. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.007
• 作为产物：
  描述：

  庚醛 、 (1'R,2S,3aS,4'R,6aS)-6-(dimethoxyphosphorylmethyl)-1',7',7'-trimethylspiro[3a,6a-dihydrocyclopenta[d][1,3]dioxole-2,2'-bicyclo[2.2.1]heptane]-4-one 在 lithium perchlorate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 以78%的产率得到(1'R,2S,3aS,4'R,6aS)-1',7',7'-trimethyl-6-[(E)-oct-1-enyl]spiro[3a,6a-dihydrocyclopenta[d][1,3]dioxole-2,2'-bicyclo[2.2.1]heptane]-4-one
  参考文献：
  名称：

  Stereocontrolled synthesis of enantiopure anticancer cyclopentenone prostaglandin analogues: (−)- and (+)-TEI-9826

  摘要：

  The synthesis of both enantiomers of TEI-9826 has been accomplished in seven steps with an overall yield of 44% starting from diastereomeric camphor protected 3-[(dimethoxyphosphoryl)methyl]-4,5-dihydroxycyclopent-2-enones. The key steps include a fully diastereoselective hydrogenation of the endocyclic carbon-carbon double bond in the cyclopentenone ring controlled with a chiral diol moiety and the conversion of the latter into a new transposed olefinic bond. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.007