5-methyl-2-(p-N,N'-dimethylamino-phenyl)-4-acetyloxazole | 157166-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-methyl-2-(p-N,N'-dimethylamino-phenyl)-4-acetyloxazole
• 英文别名: 4-acetyl-2-(p-dimethylaminophenyl)-5-methyloxazole；MDMAPAO；1-[2-[4-(Dimethylamino)phenyl]-5-methyl-1,3-oxazol-4-yl]ethanone；1-[2-[4-(dimethylamino)phenyl]-5-methyl-1,3-oxazol-4-yl]ethanone
• CAS: 157166-32-0
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: KUCZTETZQBJHBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methyl-2-(p-N,N'-dimethylamino-phenyl)-4-acetyloxazole 在 氢氧化钾 、 potassium tert-butylate 、 乙酸酐 作用下， 反应 4.0h， 生成 <2-(p-dimethylaminophenyl)oxazol-4-yl>fulgide
  参考文献：
  名称：

  Photochromism of Heterocyclic Fulgides

  摘要：

  例如，制备了 2-[1-（2-取代的 5-甲基-4-恶唑基）亚乙基]-3-异亚丙基丁二酸酐和 2-[1-（5-取代的 2-甲基-3-噻吩基）亚乙基或甲基]-3-异亚丙基丁二酸酐。此外，还研究了取代基对光致变色性能的影响；结果表明，取代基对红移有影响，并能显著增加有色形式的颜色强度。不过，褪色反应的速率也会受到取代基的影响而降低。

  DOI：

  10.1246/bcsj.65.1262
• 作为产物：
  描述：

  对二甲氨基苯甲醛 、 2,3,4-戊三酮肟 (6ci,7ci,8ci,9ci) 以48%的产率得到5-methyl-2-(p-N,N'-dimethylamino-phenyl)-4-acetyloxazole
  参考文献：
  名称：

  Photochromism of Heterocyclic Fulgides

  摘要：

  例如，制备了 2-[1-（2-取代的 5-甲基-4-恶唑基）亚乙基]-3-异亚丙基丁二酸酐和 2-[1-（5-取代的 2-甲基-3-噻吩基）亚乙基或甲基]-3-异亚丙基丁二酸酐。此外，还研究了取代基对光致变色性能的影响；结果表明，取代基对红移有影响，并能显著增加有色形式的颜色强度。不过，褪色反应的速率也会受到取代基的影响而降低。

  DOI：

  10.1246/bcsj.65.1262

文献信息

• Photochromism of Heterocyclic Fulgides
  作者：Akihiko Tomoda、Akira Kaneko、Hideki Tsuboi、Ryouka Matsushima

  DOI：10.1246/bcsj.65.1262

  日期：1992.5

  Aiming at practical uses of photochromic compounds as data-storage media, electron-donating (e.g. p-dimethylaminophenyl) and conjugate chain (e.g. p-dimethylaminostyryl) substituted heterocyclic fulgides, e.g. 2-[1-(2-substituted 5-methyl-4-oxazolyl)ethylidene]-3-isopropylidenesuccinic anhydride and 2-[1-(5-substituted 2-methyl-3-thienyl)ethylidene or methlyene]-3-isopropylidenesuccinic anhydride, were prepared. The effect on photochromic performance was also investigated; it was clarified that substituents had effects on the red-shift and a significant increase in the color intensity of a colored form. However, the rate of the discoloration reaction was also affected, depressed, by the substituent.

  例如，制备了 2-[1-（2-取代的 5-甲基-4-恶唑基）亚乙基]-3-异亚丙基丁二酸酐和 2-[1-（5-取代的 2-甲基-3-噻吩基）亚乙基或甲基]-3-异亚丙基丁二酸酐。此外，还研究了取代基对光致变色性能的影响；结果表明，取代基对红移有影响，并能显著增加有色形式的颜色强度。不过，褪色反应的速率也会受到取代基的影响而降低。
• Synthesis and photophysical studies of oxazole rings containing compounds as electron accepting units
  作者：Caihong Zhang、Lifeng Li、Hongjuan Wu、Zhixun Liu、Junfen Li、Guomei Zhang、Guangming Wen、Shaomin Shuang、Chuan Dong、Martin M.F. Choi

  DOI：10.1016/j.saa.2012.10.005

  日期：2013.2

  A series of oxazole derivatives, 5-methyl-2-(p-methylphenyl)-4-acetyl oxazole (MMPAO), 5-methyl-2-(p-methoxyphenyl)-4-acetyl oxazole (MOPAO), 5-methyl-2-(p-N,N'-dimethylamino-phenyl)-4-acetyl oxazole (MDMAPAO) and 5-methyl-2-(p-N,N-diphenylaminophenyl)-4-acetyl oxazole (MDPAPAO) have been synthesized and studied to compare their photophysical properties. The UV-visible absorption spectra of MDMAPAO and MDPAPAO are bathochromatically shifted as compared to that of MMPAO and MOPAO. The fluorescence emission of MDPAPAO is very sensitive to the polarity of solvents. The magnitude of change in the dipole moment was calculated using the Lippert-Mataga equation. MDPAPAO shows the highest change in the dipole moment (Delta u = 13.3D) than that of the other three oxazole derivatives. The spectral properties including fluorescence quantum yield and lifetime were determined in solvents with different polarities. MDPAPAO displays the highest fluorescence quantum yield and lifetime, following a bi-exponential fluorescent decay fashion. Our result demonstrates that the excited state of MDPAPAO possesses the property of intramolecular charge transfer. (C) 2012 Elsevier B.V. All rights reserved.