(E)-4-[(1R,3R,4S,6R,7R,9R)-4-bromo-3-ethyl-6-hydroxy-2,8-dioxabicyclo[5.2.1]decan-9-yl]but-2-enal | 1093122-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (E)-4-[(1R,3R,4S,6R,7R,9R)-4-bromo-3-ethyl-6-hydroxy-2,8-dioxabicyclo[5.2.1]decan-9-yl]but-2-enal
• CAS: 1093122-11-2
• 化学式: C₁₄H₂₁BrO₄
• 分子量: 333.222
• InChiKey: CJTOBKVQUCIEJQ-ROSQNVIZSA-N

物化性质

• 沸点：
  462.4±45.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-[(1R,3R,4S,6R,7R,9R)-4-bromo-3-ethyl-6-hydroxy-2,8-dioxabicyclo[5.2.1]decan-9-yl]but-2-enal 、 三甲基硅烷化重氮甲烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以85%的产率得到4-溴-3-乙基-9-戊-2-烯-4-炔基-2,8-二氧杂双环[5.2.1]癸烷-6-醇
  参考文献：
  名称：

  Biomimetic Asymmetric Total Synthesis of (−)-Laurefucin via an Organoselenium-Mediated Intramolecular Hydroxyetherification

  摘要：

  The first asymmetric total synthesis of (-)-laurefucin (1), a unique C-15 acetogenin with a 2,8-dioxabicyclo[5.2.1]decane skeleton, has been accomplished in nine steps in 31% overall yield from known oxocene 10. Highlights of the highly stereoselective synthesis include a novel organoselenium-mediated biomimetic hydroxyetherification.

  DOI：

  10.1021/ja806304s
• 作为产物：
  描述：

  丁烯-2-醛 、 (1R,3R,4S,6R,7R,9R)-4-bromo-3-ethyl-9-prop-2-enyl-2,8-dioxabicyclo[5.2.1]decan-6-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(E)-4-[(1R,3R,4S,6R,7R,9R)-4-bromo-3-ethyl-6-hydroxy-2,8-dioxabicyclo[5.2.1]decan-9-yl]but-2-enal
  参考文献：
  名称：

  Biomimetic Asymmetric Total Synthesis of (−)-Laurefucin via an Organoselenium-Mediated Intramolecular Hydroxyetherification

  摘要：

  The first asymmetric total synthesis of (-)-laurefucin (1), a unique C-15 acetogenin with a 2,8-dioxabicyclo[5.2.1]decane skeleton, has been accomplished in nine steps in 31% overall yield from known oxocene 10. Highlights of the highly stereoselective synthesis include a novel organoselenium-mediated biomimetic hydroxyetherification.

  DOI：

  10.1021/ja806304s

文献信息

• Biomimetic Asymmetric Total Synthesis of (−)-Laurefucin via an Organoselenium-Mediated Intramolecular Hydroxyetherification
  作者：Byungsook Kim、Miseon Lee、Mi Jung Kim、Hyunjoo Lee、Sanghee Kim、Deukjoon Kim、Minseob Koh、Seung Bum Park、Kye Jung Shin

  DOI：10.1021/ja806304s

  日期：2008.12.10

  The first asymmetric total synthesis of (-)-laurefucin (1), a unique C-15 acetogenin with a 2,8-dioxabicyclo[5.2.1]decane skeleton, has been accomplished in nine steps in 31% overall yield from known oxocene 10. Highlights of the highly stereoselective synthesis include a novel organoselenium-mediated biomimetic hydroxyetherification.