methyl 2-ethyl-4-oxo-4H-pyran-3-yloxyethanoate | 148115-81-5

• 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 2-ethyl-4-oxo-4H-pyran-3-yloxyethanoate
• 英文别名: Methyl 2-(2-ethyl-4-oxopyran-3-yl)oxyacetate
• CAS: 148115-81-5
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: FMZZYQDALWSJNQ-UHFFFAOYSA-N

物化性质

• 沸点：
  373.3±42.0 °C(predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-ethyl-4-oxo-4H-pyran-3-yloxyethanoate 在 sodium hydroxide 、 水 、 hydroxide 作用下， 反应 19.0h， 生成 2-(1,2-Diethyl-4-oxopyridin-3-yl)oxyacetic acid
  参考文献：
  名称：

  Study of hydrogen bonding in 1-ethyl-2-methyl-4-oxo-1,4-dihydro-pyridin-3-yloxyethanoic acid and 3-(1,2-diethyl-4-oxo-1,4-dihydropyridin-3-yloxy)propanoic acid by 1H NMR spectroscopy and X-ray crystallography

  摘要：

  A series of 1,2-dialkyl-4-oxo-1,4-dihydropyridin-3-yloxyethanoic acids and 3-(1,2-dialkyl-4-oxo-1,4-dihydropyridin-3-yloxy)propanoic acids have been synthesized via the corresponding pyran-4-ones. Ring proton chemical shifts indicate hydrogen bonding between the side-chain carboxylic acid proton and the 4-oxo group of the heterocycle to be present only for the pyridinone species in DMSO solution. X-Ray crystallography demonstrates the hydrogen bonding in 1-ethyl-2-methyl-4-oxo-1,4-dihydropyridin-3-yloxyethanoic acid to be very strong (O-O = 2.441 angstrom) and intramolecular, giving a unique 8-membered chelate ring. The analogous hydrogen bonding in 3-(1,2-diethyl-4-oxo-1,4-dihydropyridin-3-yloxy)propanoic acid is however strong (O-O = 2.541 angstrom) and intermolecular, giving an infinite structure.

  DOI：

  10.1039/p29930000451
• 作为产物：
  描述：

  甲醇 、 乙基麦芽酚 、 溴乙酸乙酯 在 sodium hydroxide 作用下， 反应 18.0h， 以36%的产率得到methyl 2-ethyl-4-oxo-4H-pyran-3-yloxyethanoate
  参考文献：
  名称：

  Study of hydrogen bonding in 1-ethyl-2-methyl-4-oxo-1,4-dihydro-pyridin-3-yloxyethanoic acid and 3-(1,2-diethyl-4-oxo-1,4-dihydropyridin-3-yloxy)propanoic acid by 1H NMR spectroscopy and X-ray crystallography

  摘要：

  A series of 1,2-dialkyl-4-oxo-1,4-dihydropyridin-3-yloxyethanoic acids and 3-(1,2-dialkyl-4-oxo-1,4-dihydropyridin-3-yloxy)propanoic acids have been synthesized via the corresponding pyran-4-ones. Ring proton chemical shifts indicate hydrogen bonding between the side-chain carboxylic acid proton and the 4-oxo group of the heterocycle to be present only for the pyridinone species in DMSO solution. X-Ray crystallography demonstrates the hydrogen bonding in 1-ethyl-2-methyl-4-oxo-1,4-dihydropyridin-3-yloxyethanoic acid to be very strong (O-O = 2.441 angstrom) and intramolecular, giving a unique 8-membered chelate ring. The analogous hydrogen bonding in 3-(1,2-diethyl-4-oxo-1,4-dihydropyridin-3-yloxy)propanoic acid is however strong (O-O = 2.541 angstrom) and intermolecular, giving an infinite structure.

  DOI：

  10.1039/p29930000451