(+)-2-(furan-3-yl)-5-vinyl-3,6-dihydro-2H-pyran | 753002-43-6

• 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-(furan-3-yl)-5-vinyl-3,6-dihydro-2H-pyran
• 英文别名: (R)-2-(furan-3-yl)-5-vinyl-3,6-dihydro-2H-pyran；(2R)-5-ethenyl-2-(furan-3-yl)-3,6-dihydro-2H-pyran
• CAS: 753002-43-6
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: NUVQSVRDNKTGFU-LLVKDONJSA-N

物化性质

• 沸点：
  258.8±40.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-2-(furan-3-yl)-5-vinyl-3,6-dihydro-2H-pyran 在 9-硼双环[3.3.1]壬烷 、 sodium hydroxide 、 乙醇 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以87%的产率得到(+)-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
• 作为产物：
  描述：

  3-糠醛 在 Grubbs catalyst first generation 乙烯 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 (+)-2-(furan-3-yl)-5-vinyl-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

文献信息

• Enantioselective Access to Key Intermediates for Salvinorin A and Analogues
  作者：Don Antoine Lanfranchi、Christophe Bour、Gilles Hanquet

  DOI：10.1002/ejoc.201100207

  日期：2011.5

  Access to enantiopure synthetic platforms that can generate key intermediates for salvinorin A analogues through diastereoselective Diels-Alder cycloaddition between an enantiopure sulfinylquinone and semicyclic dienes is described.

  描述了通过对映体纯亚磺酰基醌和半环二烯之间的非对映选择性 Diels-Alder 环加成反应，获得对映体纯合成平台的途径，该平台可以生成 Salvinorin A 类似物的关键中间体。
• Total Syntheses of (+)- and (−)-Cacospongionolide B, Cacospongionolide E, and Related Analogues. Preliminary Study of Structural Features Required for Phospholipase A₂ Inhibition
  作者：Atwood K. Cheung、Ryan Murelli、Marc L. Snapper

  DOI：10.1021/jo049285e

  日期：2004.8.1

  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.