(Z)-1-(Acetyloxy)-2-methyl-1-penten-4-one | 145663-41-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-1-(Acetyloxy)-2-methyl-1-penten-4-one
• 英文别名: InChI=1/C8H12O3/c1-6(4-7(2)9)5-11-8(3)10/h5H,4H2,1-3H3/b6-5；[(Z)-2-methyl-4-oxopent-1-enyl] acetate
• CAS: 145663-41-8
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: NSFALHRHEKUWSU-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,4,6-trimethylpyrylium tetrafluoroborate 在 sodium dihydrogenphosphate 、 双氧水 作用下， 以 水 为溶剂， 反应 0.33h， 以3%的产率得到(Z)-1-(Acetyloxy)-2-methyl-1-penten-4-one
  参考文献：
  名称：

  Hydrogen peroxide oxidation of polysubstituted pyrylium salts: formation of enol esters and furans

  摘要：

  2,4,6-Trialkylsubstituted pyrylium salts 1 have been known lo afford 2-acyl-3,5-dialkyl-furans 2 in moderate yields (30 - 45%). Oxidation of these salts in buffer solutions (pH = 3 - 4.5) increased the yields of acylfurans to 75%. In contrast, tetra- and penta-substituted pyrylium salts are mainly converted into enol esters with a delta-keto group and furans all originating presumably by C-O bond cleavages in a common intermediate. This intermediate may result by a C-O acyl shift as inferred from analogous compounds with deuterium labelling.

  DOI：

  10.1016/s0040-4020(01)92277-x

文献信息

• Hydrogen peroxide oxidation of polysubstituted pyrylium salts: formation of enol esters and furans
  作者：Teodor Silviu Balaban、Monika Hiegemann

  DOI：10.1016/s0040-4020(01)92277-x

  日期：1992.11

  2,4,6-Trialkylsubstituted pyrylium salts 1 have been known lo afford 2-acyl-3,5-dialkyl-furans 2 in moderate yields (30 - 45%). Oxidation of these salts in buffer solutions (pH = 3 - 4.5) increased the yields of acylfurans to 75%. In contrast, tetra- and penta-substituted pyrylium salts are mainly converted into enol esters with a delta-keto group and furans all originating presumably by C-O bond cleavages in a common intermediate. This intermediate may result by a C-O acyl shift as inferred from analogous compounds with deuterium labelling.

表征谱图