4-methoxy-6-phenacyl-2H-pyran-2-one | 27181-44-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 卡瓦内酯
• 英文名称: 4-methoxy-6-phenacyl-2H-pyran-2-one
• 英文别名: 4-Methoxy-6-phenacyl-2-pyron；4-Methoxy-6-benzoylmethyl-2-pyron；4-methoxy-6-(2-oxo-2-phenyl-ethyl)-pyran-2-one；4-Methoxy-6-phenacylpyran-2-one
• CAS: 27181-44-8
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: TUPRKNXZACABIL-UHFFFAOYSA-N

物化性质

• 熔点：
  135 °C(Solv: ethanol (64-17-5))
• 沸点：
  455.5±40.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-6-phenacyl-2H-pyran-2-one 在 碘代三甲硅烷 作用下， 以 氯仿 为溶剂， 反应 40.0h， 以52%的产率得到4-hydroxy-6-(2-oxo-2-phenylethyl)-2H-pyran-2-one
  参考文献：
  名称：

  通过4,6-二甲氧基-2-吡喃酮与单和二酮阴离子的缩合反应制备3,5,7-三酮和3,5,7,9-四酮酸的烯醇内酯

  摘要：

  丙酮，苯乙酮，乙酰丙酮和苯甲酰丙酮的阴离子与4,6-二甲氧基-2-吡喃酮的缩合得到相应的6个取代的4-甲氧基-2-吡喃酮的良好收率，将其通过碘代三甲基硅烷脱甲基转化为4-羟基类似物。 。

  DOI：

  10.1016/s0040-4039(00)87236-6
• 作为产物：
  描述：

  4-甲氧基-6-甲基-2H-吡喃酮 在 甲基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 4-methoxy-6-phenacyl-2H-pyran-2-one
  参考文献：
  名称：

  摘要：

  Deprotonation at the 6-methyl group of 4-methoxy-6-methyl-3-trimethylsilyl-2H-pyran-2-one (1d) resulted in the formation of an extended enolate (1e) which was spectroscopically identified. The utility of this enolate towards the synthesis of some natural products of polyketide origin has been described, e.g. the synthesis of 4-methoxy-6-(2-oxopropyl)-2H-pyran- 2-one (4) and 4-methoxy-6-phenacyl-2H-pyran-2-one (5), the former having been isolated from Penicillium stipitatum culture, and the synthesis of 5,6-dehydrokawain (6), a natural product extracted from the wood of Aniba formula and from the seeds of Alpina blepharocalyx.

  DOI：

  10.1071/ch99119

文献信息

• RAY, J. A.;HARRIS, T. M., TETRAHEDRON LETT., 1982, 23, N 19, 1971-1974
  作者：RAY, J. A.、HARRIS, T. M.

  DOI：——

  日期：——
• Preparation of enol lactones of 3,5,7-triketo and 3,5,7,9-tetraketo acids by the condensation of 4,6-dimethoxy-2-pyrone with anions of mono- and diketones
  作者：John A. Ray、Thomas M. Harris

  DOI：10.1016/s0040-4039(00)87236-6

  日期：1982.1

  Condensation of the anions of acetone, acetophenone, acetylacetone and benzoylacetone with 4,6-dimethoxy-2-pyrone afforded good yields of the corresponding 6 substituted 4-methoxy-2-pyrones which were converted to the 4-hydroxy analogs by demethylation with iodotrimethylsilane.

  丙酮，苯乙酮，乙酰丙酮和苯甲酰丙酮的阴离子与4,6-二甲氧基-2-吡喃酮的缩合得到相应的6个取代的4-甲氧基-2-吡喃酮的良好收率，将其通过碘代三甲基硅烷脱甲基转化为4-羟基类似物。 。
• ——
  作者：Younis M. Younis、Shar S. Al-Shihry

  DOI：10.1071/ch99119

  日期：——

  Deprotonation at the 6-methyl group of 4-methoxy-6-methyl-3-trimethylsilyl-2H-pyran-2-one (1d) resulted in the formation of an extended enolate (1e) which was spectroscopically identified. The utility of this enolate towards the synthesis of some natural products of polyketide origin has been described, e.g. the synthesis of 4-methoxy-6-(2-oxopropyl)-2H-pyran- 2-one (4) and 4-methoxy-6-phenacyl-2H-pyran-2-one (5), the former having been isolated from Penicillium stipitatum culture, and the synthesis of 5,6-dehydrokawain (6), a natural product extracted from the wood of Aniba formula and from the seeds of Alpina blepharocalyx.