4-methoxy-6-methyl-3-trimethylsilyl-2H-pyran-2-one | 77037-53-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-methoxy-6-methyl-3-trimethylsilyl-2H-pyran-2-one
• 英文别名: 4-Methoxy-6-methyl-3-trimethylsilylpyran-2-one
• CAS: 77037-53-7
• 化学式: C₁₀H₁₆O₃Si
• 分子量: 212.321
• InChiKey: VQLAZOCDRPCVDL-UHFFFAOYSA-N

物化性质

• 沸点：
  258.8±40.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 4-methoxy-6-methyl-3-trimethylsilyl-2H-pyran-2-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到
  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
• 作为产物：
  描述：

  4-甲氧基-6-甲基-2H-吡喃酮 、 三甲基氯硅烷 在 正丁基锂 作用下， 以45%的产率得到4-methoxy-6-methyl-3-trimethylsilyl-2H-pyran-2-one
  参考文献：
  名称：

  吡咯环上乙烯基碳的新型动力学去质子化。

  摘要：

  用丁基锂或二异丙基氨基锂锂处理4-甲氧基-α-吡喃酮导致在吡喃环的C（3）处快速去质子化，从而得到中等稳定的乙烯基碳负离子。

  DOI：

  10.1039/c39800001227

文献信息

• A novel kinetic deprotonation at a vinylic carbon in a pyrone ring
  作者：T. Adrian Carpenter、Peter J. Jenner、Finian J. Leeper、James Staunton

  DOI：10.1039/c39800001227

  日期：——

  Treatment of 4-methoxy-α-pyrones with butyllithium or lithium di-isopropylamide causes rapid deprotonation at C(3) of the pyrone ring to give moderately stable vinylic carbanions.

  用丁基锂或二异丙基氨基锂锂处理4-甲氧基-α-吡喃酮导致在吡喃环的C（3）处快速去质子化，从而得到中等稳定的乙烯基碳负离子。
• ——
  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.