methyl (1R,4R,5S)-3-oxo-2-oxabicyclo[2.2.2]oct-7-ene-5-carboxylate | 144406-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl (1R,4R,5S)-3-oxo-2-oxabicyclo[2.2.2]oct-7-ene-5-carboxylate
• CAS: 144406-83-7；144489-95-2
• 化学式: C₉H₁₀O₄
• 分子量: 182.176
• InChiKey: DBYMDPSPGLQYII-XVMARJQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2H-吡喃-2-酮 、 丙烯酸甲酯（MA） 以 二氯甲烷 为溶剂， 生成 methyl (1S,4S,5S)-3-oxo-2-oxabicyclo[2.2.2]oct-7-ene-5-carboxylate 、 methyl (1R,4R,5S)-3-oxo-2-oxabicyclo[2.2.2]oct-7-ene-5-carboxylate 、 methyl (1S,4S,6S)-3-oxo-2-oxabicyclo[2.2.2]oct-7-ene-6-carboxylate 、 methyl (1S,4S,6R)-3-oxo-2-oxabicyclo[2.2.2]oct-7-ene-6-carboxylate
  参考文献：
  名称：

  Tandem pericyclic reactions. The first X-Ray structure of an initial pyrone-olefin adduct and an easy, stereocontrolled, entry into polyoxygenated cyclohexanes

  摘要：

  Under high-pressure conditions, 2-pyrone undergoes Diels-Alder reaction with a variety of dienophiles, leading to isolable, bridged, bicyclic lactones. The first X-Ray structure of one of these lactones and its conversion into polyoxygenated cyclohexane derivatives is reported.

  DOI：

  10.1016/s0040-4039(00)61170-x