(E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)prop-2-en-1-one
• 英文别名: (E)-3-(2-chloro-6-methyl-3-quinolyl)-1-(5-hydroxy-2,2-dimethyl-chromen-6-yl)prop-2-en-1-one；(E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(5-hydroxy-2,2-dimethylchromen-6-yl)prop-2-en-1-one
• 化学式: C₂₄H₂₀ClNO₃
• 分子量: 405.881
• InChiKey: BDOGYIJAQGWNNT-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲基乙酰苯胺 在 potassium hydroxide 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 66.33h， 生成 (E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, structural elucidation, intramolecular hydrogen bonding and DFT studies of quinoline-chalcone-chromene hybrids

  摘要：

  Eight hydroxyquinoline-chromene chalcones, of which six were new, were synthesized using the Vilsmeier-Haack reaction and Claisen-Schmidt condensation. These contain either mono or dichromene functionality. The hydroxyl proton chemical shift of both types of compounds at varying temperature indicated weakened hydrogen bonds with an increase in temperature, however there was no significant difference to the slopes of the OH chemical shift curves (3.4 x10(-3) for the 2-methoxychromene derivative and 3.1 x10(-3) for the 6-methoxydichromene derivative. Potential energy scans of these two compounds were obtained using B3LYP/6-311 G level theory in the gas phase, and showed the enol form to be most stable for both molecules and that the energy barrier to make proton transfer possible is 5.076 and 3.989 Kcal mol(-1) for the 2-methoxychromene and 6-methoxydichromene derivatives respectively.[GRAPHICS].

  DOI：

  10.24820/ark.5550190.p011.193

文献信息

• Synthesis, structural elucidation, intramolecular hydrogen bonding and DFT studies of quinoline-chalcone-chromene hybrids
  作者：Lamla Thungatha、Saba Alapour、Neil A. Koorbanally

  DOI：10.24820/ark.5550190.p011.193

  日期：——

  Eight hydroxyquinoline-chromene chalcones, of which six were new, were synthesized using the Vilsmeier-Haack reaction and Claisen-Schmidt condensation. These contain either mono or dichromene functionality. The hydroxyl proton chemical shift of both types of compounds at varying temperature indicated weakened hydrogen bonds with an increase in temperature, however there was no significant difference to the slopes of the OH chemical shift curves (3.4 x10(-3) for the 2-methoxychromene derivative and 3.1 x10(-3) for the 6-methoxydichromene derivative. Potential energy scans of these two compounds were obtained using B3LYP/6-311 G level theory in the gas phase, and showed the enol form to be most stable for both molecules and that the energy barrier to make proton transfer possible is 5.076 and 3.989 Kcal mol(-1) for the 2-methoxychromene and 6-methoxydichromene derivatives respectively.[GRAPHICS].