(+)-2-[6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl]-ethanol | 753002-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (+)-2-[6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl]-ethanol
• 英文别名: 2-[(2R)-2-(furan-3-yl)-3,6-dihydro-2H-pyran-5-yl]ethanol
• CAS: 753002-44-7
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: OYWJDRXYRBZSLP-LLVKDONJSA-N

物化性质

• 沸点：
  306.1±42.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  42.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-2-[6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl]-ethanol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 1.0h， 以83%的产率得到(+)-2-(furan-3-yl)-5-(2-iodoethyl)-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  Total Syntheses of (+)- and (−)-Cacospongionolide B, Cacospongionolide E, and Related Analogues. Preliminary Study of Structural Features Required for Phospholipase A₂ Inhibition

  摘要：

  The total syntheses of the antiinflammatory marine sponge metabolites (+)-cacospongionolide B and E are described. The pivotal steps in the synthetic route include a three-step sequence that couples the two main regions of the natural product, as well as generates the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that the cacospongionolides have enantiospecific interactions with the enzyme that may be independent of the gamma-hydroxybutenolide moiety.

  DOI：

  10.1021/jo049285e
• 作为产物：
  描述：

  3-糠醛 在 Grubbs catalyst first generation 乙烯 、 sodium hydride 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 苯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 (+)-2-[6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl]-ethanol
  参考文献：
  名称：

  Total Syntheses of (+)- and (−)-Cacospongionolide B, Cacospongionolide E, and Related Analogues. Preliminary Study of Structural Features Required for Phospholipase A₂ Inhibition

  摘要：

  The total syntheses of the antiinflammatory marine sponge metabolites (+)-cacospongionolide B and E are described. The pivotal steps in the synthetic route include a three-step sequence that couples the two main regions of the natural product, as well as generates the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that the cacospongionolides have enantiospecific interactions with the enzyme that may be independent of the gamma-hydroxybutenolide moiety.

  DOI：

  10.1021/jo049285e