5-(5-chloro-2-benzotriazolyl)-6-hydroxy-1,4-dimethyl-3-carbonitrile-2-pyridone | 1391866-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并吡啶类
• 英文名称: 5-(5-chloro-2-benzotriazolyl)-6-hydroxy-1,4-dimethyl-3-carbonitrile-2-pyridone
• CAS: 1391866-66-2
• 化学式: C₁₄H₁₀ClN₅O₂
• 分子量: 315.719
• InChiKey: AMUBXBTUZSODOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  96.73
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  5-[(4-chloro-2-nitrophenyl)hydrazinylidene]-1,4-dimethyl-2,6-dioxopyridine-3-carbonitrile 在 二氧化硫脲 、 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以86%的产率得到5-(5-chloro-2-benzotriazolyl)-6-hydroxy-1,4-dimethyl-3-carbonitrile-2-pyridone
  参考文献：
  名称：

  Synthesis, spectroscopic properties and applications of novel N-heterocycle-containing benzotriazoles as UV absorbers

  摘要：

  Two novel N-heterocycle-containing benzotriazole compounds, 5-(5-chloro-2-benzotriazolyl)-6-hydroxy-1,4-dimethyl-3-carbonitrile-2-pyridone (2) and 4-(5-chloro-2-benzotriazolyl)-5-methyl-2-phenyl-3-pyrazolone (4), were synthesized from reactant 4-chloro-2-nitroaniline via diazotization, azo coupling, reductive cyclization and acidification. Their structures were confirmed by FT-IR. H-1 NMR, mass spectroscopy and elemental analysis. Their spectral properties were investigated and compared with that of a common commercial benzotriazole UV absorber Tinuvin 326. It is found that the novel N-heterocycle-containing benzotriazole compounds exhibit sharp single peak in the range of 280-400 nm and have much higher molar extinction coefficients than that of Tinuvin 326. Their anti-UV protection properties on polyester fabric were also evaluated and compound 4 was much superior to compound 2 due to its higher exhaustion. (C) 2012 Zhi Hua Cui. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.06.024

文献信息

• Structure and properties of N-heterocycle-containing benzotriazoles as UV absorbers
  作者：Zhihua Cui、Xin Li、Xidong Wang、Kemei Pei、Weiguo Chen

  DOI：10.1016/j.molstruc.2013.09.045

  日期：2013.12

  Two N-heterocycle-containing benzotriazole compounds (CBHDCP, CBMPP) were synthesized and their structures were confirmed by FT-IR, H-1 NMR, mass spectroscopy and elemental analysis. Their spectral properties compared with that of a common commercial benzotriazole UV absorber Tinuvin 326 in solvents were measured and analyzed using molecular orbital calculations. It was found that the experimentally obtained optical properties were in close agreement with the theoretically obtained results. Besides, CBMPP is much superior to CBHDCP acting as an effective UV absorber on polyethylene terephthalate fabric due to its combinative higher exhaustion and higher molar extinction coefficient. The exhaustion difference on polyethylene terephthalate fabric among N-heterocycle-containing benzotriazoles (CBHDCP, CBMPP) and Tinuvin 326 were then measured and explained by the solubility parameter theory. The results agreed with the rule that compounds with higher exhaustion on fiber have solubility parameter much closer to that of fiber polymer. (C) 2013 Elsevier B.V. All rights reserved.