3-pyridylmethyl 2,6,6-trimethyl-4-(2-fluoro-3-trifluoromethylphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate | 1282581-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-pyridylmethyl 2,6,6-trimethyl-4-(2-fluoro-3-trifluoromethylphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
• 英文别名: 3-pyridylmethyl 4-[2-fluoro-3-(trifluoromethyl)phenyl]-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；Pyridin-3-ylmethyl 4-[2-fluoro-3-(trifluoromethyl)phenyl]-2,6,6-trimethyl-5-oxo-1,4,7,8-tetrahydroquinoline-3-carboxylate
• CAS: 1282581-82-1
• 化学式: C₂₆H₂₄F₄N₂O₃
• 分子量: 488.482
• InChiKey: CNCQBPIZTWYCMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-吡啶甲醇 在 ammonium acetate 作用下， 以 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 9.0h， 生成 3-pyridylmethyl 2,6,6-trimethyl-4-(2-fluoro-3-trifluoromethylphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  1,4-二氢吡啶类化合物在离体兔胃底的合成及髓鞘活性

  摘要：

  战略，管理与卫生政策 临床前研究

  DOI：

  10.1002/ddr.21024

文献信息

• Two 1,4-dihydropyridine derivatives with potential calcium-channel antagonist activity
  作者：Anthony Linden、Cihat Şafak、Rahime Şimşek、Miyase G. Gündüz

  DOI：10.1107/s0108270111003362

  日期：2011.2.15

  The title compounds, benzyl 4-(3-chloro-2-fluorophenyl)-2-methyl-5-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carboxylate, C23H19ClFNO3, (I), and 3-pyridylmethyl 4-[2-fluoro-3-(trifluoromethyl)phenyl]-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C26H24F4N2O3, (II), belong to a class of 1,4-dihydropyridines whose members sometimes display calcium modulatory properties. The 1,4-dihydropyridine ring in each structure has a shallower than usual shallow-boat conformation and is nearly planar in (I). In each structure, the halogen-substituted benzene ring is oriented such that the halogen substituents are in a synperiplanar orientation with respect to the 1,4-dihydropyridine ring plane. The oxocyclopentene ring in (I) is planar, while the oxocyclohexene ring in (II) has a half-chair conformation, which is less commonly observed than the envelope conformation usually found in related compounds. In (I), the frequently observed intermolecular N-H...O hydrogen bond between the amine group and the carbonyl O atom of the oxocyclopentene ring of a neighbouring molecule links the molecules into extended chains; there are no other significant intermolecular interactions. By contrast, the amine group in (II) forms an N-H...N hydrogen bond with the pyridine ring N atom of a neighbouring molecule. Additional C-H...O interactions complete a two-dimensional hydrogen-bonded network. The halogen-substituted benzene ring has a weak intramolecular pi-pi interaction with the pyridine ring. A stronger pi-pi interaction occurs between the 1,4-dihydropyridine rings of centrosymmetrically related molecules.