6-methyl-2-phenylpyrazolo[4,3-c]quinolin-3-one | 866143-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-methyl-2-phenylpyrazolo[4,3-c]quinolin-3-one
• 英文别名: 6-methyl-2-phenyl-1,2-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one；6-methyl-2-phenyl-1H-pyrazolo[4,3-c]quinolin-3-one
• CAS: 866143-84-2
• 化学式: C₁₇H₁₃N₃O
• 分子量: 275.31
• InChiKey: YEHUCUKIZMEULY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基-6-甲基喹啉-3-羧酸乙酯 在 氯化亚砜 作用下， 生成 6-methyl-2-phenylpyrazolo[4,3-c]quinolin-3-one
  参考文献：
  名称：

  Structural evaluation of three 2-phenylpyrazolo[4,3-c]quinolin-3-one monohydrates

  摘要：

  A single crystal X-ray diffraction and theoretical study has been carried out on mono hydrates of three 2H-pyrazolo[4,3-c]quinolin-3(5H)-one derivatives, namely 6-methyl-2-phenylpyrazolo[4,3-c]quinolin-3-one, 3, 6-methyl-2(4-chlorophenyl)pyrazolo[4,3-c]quinolin-3-one, 4, and 8-methyl-2-(4-nitrophenyl)pyrazolo[4,3-c]quinolin-3-one, 5. The monohydrates were obtained on recrystallization from moist solvents. While there are three tautomeric forms possible for such pyrazolo[4,3-c]quinolin-3-one molecules, the sole form isolated in the solid [(X)center dot(H2O)] (X = 3, 4 and 5) compounds was the quinoloid form - the one calculated to be the most stable at the M06-2X/6-311++G(d,p) level of theory. Excellent agreement was found between the calculated and X-ray determined structures. Molecule 5 in [(5)center dot(H2O)] is very near planar while both molecules 3 and 4 in their respective hydrates are much less so as a consequence of angles about 24 between the two aromatic rings. In each hydrate, the pyrazolo[4,3-c]quinolin-3-one molecule is bonded to three water molecules and each water molecule is likewise H-bonded to three pyrazolo[4,3-c]quinolin-3-one molecules. While the water molecules are H-bonded to 3 and 4 via the pyridinyl N and 2x the carbonyl 0 atoms, in [(5)center dot(H2O)] the H-bonds are to pyridinyl N, carbonyl 0 and a nitro 0 atoms. Calculations indicated that the found arrangement in [(5)center dot(H2O)] is more stable than one using the connections as found in [(3)center dot(H2O)] and [(4)center dot(H2O)]. While each of the hydrates possess strong N-H center dot center dot center dot O and O-H center dot center dot center dot O hydrogen bonds, and weaker C-H center dot center dot center dot pi and pi center dot center dot center dot pi interactions, the supramolecular arrays are very different. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.08.032