isopropyl 6-amino-5-cyano-2-methyl-4-(1-naphthyl)-4H-pyran-3-carboxylate | 1086193-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: isopropyl 6-amino-5-cyano-2-methyl-4-(1-naphthyl)-4H-pyran-3-carboxylate
• CAS: 1086193-92-1
• 化学式: C₂₁H₂₀N₂O₃
• 分子量: 348.401
• InChiKey: VHAVOUJTFQDLCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  85.34
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  乙酰乙酸异丙酯 、 2-(萘-1-基亚甲基)丙二腈 以79%的产率得到isopropyl 6-amino-5-cyano-2-methyl-4-(1-naphthyl)-4H-pyran-3-carboxylate
  参考文献：
  名称：

  Three sterically hindered 6-amino-5-cyano-2-methyl-4-(1-naphthyl)-4H-pyran-3-carboxylate derivatives

  摘要：

  In the title compounds, 2-methoxyethyl 6-amino-5-cyano-2-methyl- 4-(1-naphthyl)-4H-pyran-3-carboxylate, C21H20N2O4, (II), isopropyl 6-amino-5-cyano-2-methyl-4-(1-naphthyl)-4H-pyran-3- carboxylate, C21H20N2O3, (III), and ethyl 6-amino-5- cyano-2-methyl-4-(1-naphthyl)-4H-pyran-3-carboxylate, C20H18N2O3, (IV), the heterocyclic pyran ring adopts a flattened boat conformation. In (II) and (III), the carbonyl group and a double bond of the heterocyclic ring are mutually anti, but in (IV) they are mutually syn. The ester O atoms in (II) and (III) and the carbonyl O atom in (IV) participate in intramolecular C-H center dot center dot center dot O contacts to form six-membered rings. The dihedral angles between the naphthalene substituent and the closest four atoms of the heterocyclic ring are 73.3 (1), 71.0 (1) and 74.3 (1)degrees for (II)-(IV), respectively. In all three structures, only one H atom of the NH2 group takes part in N-H center dot center dot center dot O [in (II) and (III)] or N-H center dot center dot center dot N [in (IV)] intermolecular hydrogen bonds, and chains [in (II) and (III)] or dimers [in (IV)] are formed. In (II), weak intermolecular C-H center dot center dot center dot O and C-H center dot center dot center dot N hydrogen bonds, and in (III) intermolecular C-H center dot center dot center dot O hydrogen bonds link the chains into ladders along the a axis.

  DOI：

  10.1107/s0108270107049001