(3-oxo-3H-benzo[f]chromen-1-yl)-acetic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (3-oxo-3H-benzo[f]chromen-1-yl)-acetic acid ethyl ester
• 英文别名: (3-Oxo-3H-benzo[f]chromen-1-yl)-essigsaeure-aethylester；(3-Oxo-3H-benzo[f]chromen-1-yl)-acetic acid ethyl ester；ethyl 2-(3-oxobenzo[f]chromen-1-yl)acetate
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: OUXGJPQKEXNLLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (3-oxo-3H-benzo[f]chromen-1-yl)-acetic acid ethyl ester 在 selenium(IV) oxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以83%的产率得到
  参考文献：
  名称：

  Mashelkar; Tungare, Shefali S.; Bhagat, Sachin, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 3, p. 315 - 320

  摘要：

  DOI：
• 作为产物：
  描述：

  2-萘酚 在 硫酸 作用下， 生成 (3-oxo-3H-benzo[f]chromen-1-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Synthetic and Structural Studies on Novel 4,3′-Bicoumarins

  摘要：

  A series of directly linked 4-3 bicoumarins have been synthesized by both Knoevenagel and Perkin reactions. This single-step transformation was accomplished by the reaction of coumarin-4-acetates with substituted salicylaldehydes in presence of piperidine using ethanol as solvent and by the reaction of coumarin-4-acetic acids with substituted salicylaldehydes in the presence of sodium hydride in acetic anhydride. Greater yields have been obtained in the sodium hydride and acetic anhydride condition. An intermediate chalcone with an ortho-hydroxyl group, which is a precursor for lactone formation, has been isolated and its structure has been confirmed by x-ray analysis. The nonplanar S-cis arrangement of two C4-C3' double bonds has been confirmed by nuclear Overhauser spectroscopy (NOE) and x-ray studies. The UV-fluorescence studies support the formation of a conjugated bicoumarin system.

  DOI：

  10.1080/00397911.2015.1063656

文献信息

• Dey, Journal of the Chemical Society, 1915, vol. 107, p. 1637
  作者：Dey

  DOI：——

  日期：——
• Synthetic and Structural Studies on Novel 4,3′-Bicoumarins
  作者：Kiran K. Pujar、Manohar V. Kulkarni、Ganesh N. Alawandi、G. N. Anilkumar、Mahantesha Basanagouda

  DOI：10.1080/00397911.2015.1063656

  日期：2015.9.2

  A series of directly linked 4-3 bicoumarins have been synthesized by both Knoevenagel and Perkin reactions. This single-step transformation was accomplished by the reaction of coumarin-4-acetates with substituted salicylaldehydes in presence of piperidine using ethanol as solvent and by the reaction of coumarin-4-acetic acids with substituted salicylaldehydes in the presence of sodium hydride in acetic anhydride. Greater yields have been obtained in the sodium hydride and acetic anhydride condition. An intermediate chalcone with an ortho-hydroxyl group, which is a precursor for lactone formation, has been isolated and its structure has been confirmed by x-ray analysis. The nonplanar S-cis arrangement of two C4-C3' double bonds has been confirmed by nuclear Overhauser spectroscopy (NOE) and x-ray studies. The UV-fluorescence studies support the formation of a conjugated bicoumarin system.
• Mashelkar; Tungare, Shefali S.; Bhagat, Sachin, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 3, p. 315 - 320
  作者：Mashelkar、Tungare, Shefali S.、Bhagat, Sachin

  DOI：——

  日期：——