(1R,2R,3a'R,4R,6a'R)-1,7,7-trimethyl-6'-((E)-oct-1-en-1-yl)-3a',6a'-dihydro-4'H-spiro[bicyclo[2.2.1]heptane-2,2'-cyclopenta[d][1,3]dioxol]-4'-one | 1268607-17-5

• 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: (1R,2R,3a'R,4R,6a'R)-1,7,7-trimethyl-6'-((E)-oct-1-en-1-yl)-3a',6a'-dihydro-4'H-spiro[bicyclo[2.2.1]heptane-2,2'-cyclopenta[d][1,3]dioxol]-4'-one
• CAS: 1268607-17-5
• 化学式: C₂₃H₃₄O₃
• 分子量: 358.521
• InChiKey: UWOCWFJDIMAGHV-IGCXSURMSA-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)：
  5.35
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (1R,2R,3a'R,4R,6a'R)-1,7,7-trimethyl-6'-((E)-oct-1-en-1-yl)-3a',6a'-dihydro-4'H-spiro[bicyclo[2.2.1]heptane-2,2'-cyclopenta[d][1,3]dioxol]-4'-one 在 aluminum amalgam 、 正丁基锂 、 10% palladium on activated carbon 、 氢气 、 对甲苯磺酸 、 异丙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 水 为溶剂， 反应 51.67h， 生成
  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,2R,3aR,4'R,6aR)-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82%的产率得到(1R,2R,3a'R,4R,6a'R)-1,7,7-trimethyl-6'-((E)-oct-1-en-1-yl)-3a',6a'-dihydro-4'H-spiro[bicyclo[2.2.1]heptane-2,2'-cyclopenta[d][1,3]dioxol]-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