1-(furan-2-yl)hex-5-en-1-d-1-ol | 1444005-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 1-(furan-2-yl)hex-5-en-1-d-1-ol
• CAS: 1444005-27-9
• 化学式: C₁₀H₁₄O₂
• 分子量: 167.212
• InChiKey: RWENKYXIYNDMBL-QOWOAITPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  33.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(furan-2-yl)hex-5-en-1-d-1-ol 在 1-甲基吡咯烷 、 吡啶 、 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 癸烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Unique Reactivity of anti- and syn-Acetoxypyranones en Route to Oxidopyrylium Intermediates Leading to a Cascade Process

  摘要：

  Unique reactivity of anti- and syn-acetoxypyranones was observed in oxidopyrylium-alkene [5 + 2] cycloadditions. The subtle interplay between the corresponding acetoxypyranone conformation and steric bulk of tertiary amine bases causes syn-acetoxypyranones to undergo [5 + 2] cycloaddition appreciably faster than anti-acetoxypyranones. Additionally, the efficiency of a cascade process that afforded a novel tetracyclic lactol was determined to be dependent on the relative stereochemistry of each diastereomer, the amine base utilized, and the addition of water.

  DOI：

  10.1021/ol4012986
• 作为产物：
  描述：

  糠醛-alpha-D1 、 5-溴-1-戊烯 在 碘 、 magnesium 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以92%的产率得到1-(furan-2-yl)hex-5-en-1-d-1-ol
  参考文献：
  名称：

  Unique Reactivity of anti- and syn-Acetoxypyranones en Route to Oxidopyrylium Intermediates Leading to a Cascade Process

  摘要：

  Unique reactivity of anti- and syn-acetoxypyranones was observed in oxidopyrylium-alkene [5 + 2] cycloadditions. The subtle interplay between the corresponding acetoxypyranone conformation and steric bulk of tertiary amine bases causes syn-acetoxypyranones to undergo [5 + 2] cycloaddition appreciably faster than anti-acetoxypyranones. Additionally, the efficiency of a cascade process that afforded a novel tetracyclic lactol was determined to be dependent on the relative stereochemistry of each diastereomer, the amine base utilized, and the addition of water.

  DOI：

  10.1021/ol4012986