1',3',3'-trimethyl-6-[(4-nitrophenyl)hydrazinylidene]spiro[benzo[f][1,4]benzoxazine-3,2'-indole]-5-one | 1430226-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1',3',3'-trimethyl-6-[(4-nitrophenyl)hydrazinylidene]spiro[benzo[f][1,4]benzoxazine-3,2'-indole]-5-one
• CAS: 1430226-15-5
• 化学式: C₂₈H₂₃N₅O₄
• 分子量: 493.522
• InChiKey: GTEFBUKBXLQBGA-UHFFFAOYSA-N

物化性质

• 沸点：
  688.2±65.0 °C(predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  37.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  109.43
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  4-硝基苯胺 在 盐酸 、 sodium hydroxide 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 1.2h， 生成 1',3',3'-trimethyl-6-[(4-nitrophenyl)hydrazinylidene]spiro[benzo[f][1,4]benzoxazine-3,2'-indole]-5-one
  参考文献：
  名称：

  The molecular design, synthesis and photochromic properties of spirooxazines containing a permanent azo (hydrazone) chromophore

  摘要：

  A range of molecular modelling techniques has been applied to predict optimized geometrical conformations and energies of the ring-closed oxazine form and ring-opened merocyanine forms of three azospirooxazines. A comparison of the relative stabilities of the possible isomers of the merocyanines was carried out by applying molecular mechanics (augmented MM2), while the prediction of the potential for photochromic behaviour was made by comparison of the heats of formation calculated by AMI. Synthetic routes were explored and as a result two azospirooxazines were isolated, one of which showed interesting and unusual photochromic behaviour. The instability of this compound towards purification by chromatography was investigated. The decomposition product was isolated and characterized with the aid of single crystal x-ray crystallography. The correlation between predicted and observed photochromic behaviour is discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.02.017