(Z)-1-[(4-amino-2,3,5,6-tetramethylphenylamino)methylene]-18a-dihydronaphthalen-2(3H)-one | 1240390-15-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-1-[(4-amino-2,3,5,6-tetramethylphenylamino)methylene]-18a-dihydronaphthalen-2(3H)-one
• CAS: 1240390-15-1
• 化学式: C₂₁H₂₂N₂O
• 分子量: 318.418
• InChiKey: QKJGXJYWQQNDGO-WQRHYEAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.12
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  四甲基对苯二胺 、 2-羟基-1-萘甲醛 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到(Z)-1-[(4-amino-2,3,5,6-tetramethylphenylamino)methylene]-18a-dihydronaphthalen-2(3H)-one
  参考文献：
  名称：

  Tautomerism in Solution and Solid State, Spectroscopic Studies and Crystal Structure of (Z)-1-[(4-amino-2,3,5,6-tetramethylphenylamino)methylene]-1,8a-dihydronaphthalen-2(3H)-one

  摘要：

  A new Schiff base compound(Z)-1-[(4-amino-2,3,5,6-tetramethylphenylamino)methylene]-1,8a-dihydronaphthalen-2(3H)-onewas synthesized by the reaction of 2-hydroxy-1-naphthaldehyde with 2,3,5,6-tetramethyl-p-phenylenediamine. It was investigated by using elemental analysis, IR, 1H-NMR, 13C-NMR, UV-Visible-spectroscopy, and X-ray-crystallography techniques. Its UV-Visible spectra were examined in polar and nonpolar solvents. The Schiff base studied exists in enol-imine keto-amine form in DMSO ethanol, chloroform, and benzene solution. The keto-amine tautomer was found to be dominant in both the phases. The (Z)-1-[(4-amino-2,3,5,6-tetramethylphenylamino)methylene]-1,8a-dihydronaphthalen-2(3H)-one molecule is not planar. It contains a strong intramolecular N-H...O hydrogen bond between the amine and oxo group [N1 and O1=2.591(2) angstrom], the H atom being essentially bonded to the N1 and O1 atoms.

  DOI：

  10.1080/00387010903284646