(1S,4S,8S)-8-Hydroxymethyl-2-oxa-bicyclo[2.2.2]oct-5-en-3-one | 137776-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,4S,8S)-8-Hydroxymethyl-2-oxa-bicyclo[2.2.2]oct-5-en-3-one
• 英文别名: (1S,4S,8S)-8-(hydroxymethyl)-2-oxabicyclo[2.2.2]oct-5-en-3-one
• CAS: 137776-69-3
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: QKCBZTBYBFWUQA-QYNIQEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-溴-2H-吡喃-2-酮 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 三正丁基氢锡 、 barium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,4S,8S)-8-Hydroxymethyl-2-oxa-bicyclo[2.2.2]oct-5-en-3-one
  参考文献：
  名称：

  3-bromo-2-pyrone: an easily prepared chameleon diene and a synthetic equivalent of 2-pyrone in thermal diels-alder cycloadditions

  摘要：

  3-Bromo-2-pyrone, a stable solid prepared by a new route (eq. 1), has been found to undergo smooth and regiospecific 2+4-cycloadditions between 78-90-degrees-C with both electron-rich and electron-deficient dienophiles; subsequent high-yield reductive debrominations produced halogen-free cycloadducts thus showing 3-bromo-2-pyrone to be a practical and effective synthetic equivalent of 2-pyrone in thermal Diels-Alder cycloadditions.

  DOI：

  10.1016/s0040-4039(00)92368-2