4-(cyclohex-2-enyloxy)-6-methylpyran-2-one | 500128-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-(cyclohex-2-enyloxy)-6-methylpyran-2-one
• CAS: 500128-30-3
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: PURWEOAZMIWHRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(cyclohex-2-enyloxy)-6-methylpyran-2-one 在 二(氰基苯)二氯化钯 sodium methylate 作用下， 以 xylene 、 苯 为溶剂， 反应 23.0h， 生成 3-methyl-1H-pyrano[4,3-b]benzofuran-1-one
  参考文献：
  名称：

  Regioselective Heterocyclization of 3-(Cyclohex-2′-enyl)-4-hydroxy-6-methylpyran-2-one

  摘要：

  Regioselective heterocyclization of 3-(cyclohex-2-enyl)-4-hydroxy-6-methyl pyran-2-one with various reagents afforded different heterocycles. With N-iodosuccinimide in acetonitrile at 0-5degreesC it gave 6-methyl-9'-iodo-2-oxabicyclo[3.3.1]nonano[3,2-c]pyran-2-one, with C5H5NHBr3 or C6H12N4HBr3 in CHCl3 at 0-5degreesC it furnished 6-methyl-9'-bromo-2'-oxabicyclo[3.3.1]nonano[3,2-c]pyran-2-one. Cold concentrated H2SO4 lead to 6-methyl-2-oxabicyclo[3.3.1]nonano[3,2-c]pyran-2-one, whereas PdCl2(PhCN)(2) in C6H6 at 80degreesC afforded 9-methyl benzofuro[3,2-c]pyran-2-one.

  DOI：

  10.1007/s007060200109
• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 、 3-溴环己烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以55%的产率得到4-(cyclohex-2-enyloxy)-6-methylpyran-2-one
  参考文献：
  名称：

  Regioselective Heterocyclization of 3-(Cyclohex-2′-enyl)-4-hydroxy-6-methylpyran-2-one

  摘要：

  Regioselective heterocyclization of 3-(cyclohex-2-enyl)-4-hydroxy-6-methyl pyran-2-one with various reagents afforded different heterocycles. With N-iodosuccinimide in acetonitrile at 0-5degreesC it gave 6-methyl-9'-iodo-2-oxabicyclo[3.3.1]nonano[3,2-c]pyran-2-one, with C5H5NHBr3 or C6H12N4HBr3 in CHCl3 at 0-5degreesC it furnished 6-methyl-9'-bromo-2'-oxabicyclo[3.3.1]nonano[3,2-c]pyran-2-one. Cold concentrated H2SO4 lead to 6-methyl-2-oxabicyclo[3.3.1]nonano[3,2-c]pyran-2-one, whereas PdCl2(PhCN)(2) in C6H6 at 80degreesC afforded 9-methyl benzofuro[3,2-c]pyran-2-one.

  DOI：

  10.1007/s007060200109