5-acetyl-2-amino-6-methyl-4-(1-naphthyl)-4H-pyran-3-carbonitrile | 300805-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-acetyl-2-amino-6-methyl-4-(1-naphthyl)-4H-pyran-3-carbonitrile
• 英文别名: 5-Acetyl-2-amino-6-methyl-4-naphthalen-1-yl-4H-pyran-3-carbonitrile
• CAS: 300805-32-7
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: VGSBOMKSYLFNPP-UHFFFAOYSA-N

物化性质

• 熔点：
  195 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  586.3±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)
• 溶解度：
  37.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(萘-1-基亚甲基)丙二腈 、 乙酰丙酮 在 吗啉 作用下， 以 乙醇 为溶剂， 以75%的产率得到5-acetyl-2-amino-6-methyl-4-(1-naphthyl)-4H-pyran-3-carbonitrile
  参考文献：
  名称：

  5-Acetyl-2-amino-6-methyl-4-(1-naphthyl)-4H-pyran-3-carbonitrile, methyl 6-amino-5-cyano-2-methyl-4-(1-naphthyl)-4H-pyran-3-carboxylate andtert-butyl 6-amino-5-cyano-2-methyl-4-(1-naphthyl)-4H-pyran-3-carboxylate

  摘要：

  Syntheses and X-ray structural investigations have been carried out for the three title compounds, C19H16N2O2, (IIIa), C19H16N2O3, (IIIb), and C22H22N2O3, (IIIc), respectively. In molecules (IIIa) and (IIIc), the heterocyclic ring is practically at, while in ( IIIb) it adopts a flattened-boat conformation. In ( IIIb) and ( IIIc), the carbonyl group and a double bond of the heterocyclic ring are anti, but in ( IIIa) they are syn and the carbonyl group participates in an intramolecular C-H...O hydrogen bond which forms a six-membered ring. In molecules ( IIIa) and ( IIIc), the dihedral angles between the naphthalene substituent and the at heterocyclic ring are 96.4 ( 3) and 102.6 ( 3)degrees, respectively. In ( IIIb), the dihedral angle between the pseudo-axial naphthalene bicycle and the at part of the pyran ring is 81.6 ( 3) degrees. In the crystal structure of (IIIa), intermolecular N-H...N and N-H...O hydrogen bonds link the molecules into a three-dimensional framework. In ( IIIb) and (IIIc), only one H atom of the NH2 group takes part in an N-H..O hydrogen bond and infinite chains are formed along the a axis.

  DOI：

  10.1107/s0108270104013812