2-(2-pyridyl)-N,N,4-triphenyl-5-thiazolamine | 1608479-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-pyridyl)-N,N,4-triphenyl-5-thiazolamine
• 英文别名: N,N,4-triphenyl-2-pyridin-2-yl-1,3-thiazol-5-amine
• CAS: 1608479-14-6
• 化学式: C₂₆H₁₉N₃S
• 分子量: 405.523
• InChiKey: AUTJKPZLLWTCRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-pyridyl)-N,N,4-triphenyl-5-thiazolamine 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以18%的产率得到
  参考文献：
  名称：

  5-Amino-2-thiazolylpyridine N-Oxides: Synthesis and Properties

  摘要：

  5-Amino-2-thiazolylpyridine N-oxides were prepared in low to moderate yields by the oxidation of 2-pyridyl-5-aminothiazoles with m-CPBA. The molecular structures of the resulting N-oxides were unequivocally determined by X-ray analyses. The N-oxides exhibited the absorption maxima at around 415 +/- 20 nm in a CHCl3 solution, while the emission spectra were observed in the range of 505 to 604 nm. The red -shift of the emission was attributed to the methoxy groups attached to the para-position of an aromatic group on the nitrogen atom at the 5-position. The N-oxides exhibited halochromism with the addition of B(C6F5)(3). The change in absorption implied the formation of a 1:1 complex between N-oxide and B(C6F5)(3). The emission wavelengths of the N-oxides were observed at 510 +/- 25 nm in a solid state. Interestingly, one of the N-oxides having methoxy groups exhibited mechanofluorochromism. The solid-state emission of the N-oxide at 527 nm shifted to a longer wavelength (599 nm) when it was subjected to grinding.

  DOI：

  10.3987/com-19-s(f)51
• 作为产物：
  描述：

  N,N-二苯基硫代甲酰胺 在 碘 作用下， 以 四氢呋喃 为溶剂， 生成 2-(2-pyridyl)-N,N,4-triphenyl-5-thiazolamine
  参考文献：
  名称：

  5-Amino-2-thiazolylpyridine N-Oxides: Synthesis and Properties

  摘要：

  5-Amino-2-thiazolylpyridine N-oxides were prepared in low to moderate yields by the oxidation of 2-pyridyl-5-aminothiazoles with m-CPBA. The molecular structures of the resulting N-oxides were unequivocally determined by X-ray analyses. The N-oxides exhibited the absorption maxima at around 415 +/- 20 nm in a CHCl3 solution, while the emission spectra were observed in the range of 505 to 604 nm. The red -shift of the emission was attributed to the methoxy groups attached to the para-position of an aromatic group on the nitrogen atom at the 5-position. The N-oxides exhibited halochromism with the addition of B(C6F5)(3). The change in absorption implied the formation of a 1:1 complex between N-oxide and B(C6F5)(3). The emission wavelengths of the N-oxides were observed at 510 +/- 25 nm in a solid state. Interestingly, one of the N-oxides having methoxy groups exhibited mechanofluorochromism. The solid-state emission of the N-oxide at 527 nm shifted to a longer wavelength (599 nm) when it was subjected to grinding.

  DOI：

  10.3987/com-19-s(f)51

文献信息

• Reaction of Selenoamide Dianions with Thio- and Selenoformamides Leading to the Formation of 5-Aminoselenazoles: Photophysical and Electrochemical Properties
  作者：Toshiaki Murai、Kirara Yamaguchi、Fumihiko Hori、Toshifumi Maruyama

  DOI：10.1021/jo500499g

  日期：2014.6.6

  5-Amino-2-selenazolines were synthesized by reacting selenoamide dianions generated from secondary selenoamides and BuLi with tertiary thio- and selenoformamides followed by treatment with iodine. The resulting 5-amino-2-selenazolines were further oxidized with iodine to give 5-aminoselenazoles in moderate to good yields. The general tendencies in the 77Se NMR spectra of the starting selenoamides,

  通过使由仲硒酰胺和BuLi生成的硒酰胺二价阴离子与叔硫代和硒甲酰胺反应，然后用碘处理，可以合成5-氨基-2-硒代唑啉。将所得的5-氨基-2-硒代唑啉进一步用碘氧化，以中等至良好的产率得到5-氨基硒代唑。77大趋势测定了起始硒酰胺，5-氨基-2-硒代唑啉和5-氨基硒唑的Se NMR谱。这些化合物的化学位移受到涉及硒原子的骨架以及每个骨架碳原子上的取代基的高度影响。通过X射线分析明确了5-氨基硒唑的分子结构，并通过DFT计算阐明了它们的电子结构。最后，对5-氨基硒代唑进行了紫外-可见光谱和荧光光谱法以及循环伏安法（CV），并讨论了它们与硒代唑环上取代基的性质。
• 5-N-Arylaminothiazoles as Highly Twisted Fluorescent Monocyclic Heterocycles: Synthesis and Characterization
  作者：Kirara Yamaguchi、Toshiaki Murai、Saki Hasegawa、Yohei Miwa、Shoichi Kutsumizu、Toshifumi Maruyama、Takahiro Sasamori、Norihiro Tokitoh

  DOI：10.1021/acs.joc.5b01963

  日期：2015.11.6

  adopt structures that are highly twisted from planar conformations. Their orientations were tuned by the steric and/or electronic interactions of the substituents at their 2-, 4-, and 5-positions. The 5-aminothiazoles exhibited a range of fluorescent emissions, from blue to orange. Although the absorption spectra were independent of the polarity of the solvent, fluorescent emissions were influenced

  通过使衍生自仲硫代酰胺的硫代酰胺二阴离子与硫代甲酰胺反应，然后依次用碘进行氧化，可以制备一系列5-N-芳基氨基噻唑。X射线分析表明，它们采用了与平面构象高度扭曲的结构。它们的取向通过在其2-，4-和5-位上的取代基的空间和/或电子相互作用来调节。5-氨基噻唑显示出从蓝色到橙色的一系列荧光发射。尽管吸收光谱与溶剂的极性无关，但荧光发射受溶剂的极性影响：在极性更大的溶剂中，发射发生红移。根据Lippert-Mataga图以及基态和激发态之间的偶极矩变化对这些现象进行了检验。它们还表现出固态发光，再次从蓝色到橙色。5-氨基噻唑的循环伏安法显示单电子氧化的可逆波。通过将电子给体基团引入到5-位氮原子上的苯基上，可以降低氧化的半电位。进行了DFT计算以确定HOMO和LUMO的能级。最后，TG-DTA的结果表明它们是热稳定的。进行了DFT计算以确定HOMO和LUMO的能级。最后，TG-DTA的结果表明
• Pyridinium 5-aminothiazoles: specific photophysical properties and vapochromism in halogenated solvents
  作者：Kirara Yamaguchi、Toshiaki Murai、Yuki Tsuchiya、Yohei Miwa、Shoichi Kutsumizu、Takahiro Sasamori、Norihiro Tokitoh

  DOI：10.1039/c7ra01896g

  日期：——

  Treatment of pyridyl-5-aminothiazoles (1–4) with alkyl triflates or benzyl iodide afforded the corresponding pyridinium 5-aminothiazoles (5–10), which exhibited bathochromically shifted absorption and fluorescence spectra relative to those of 1–4. Moreover, the vapochromic properties of 5 specific to halogenated solvents were examined by powder X-ray diffraction analysis. Pmma films containing 5 can

  用烷基三氟甲磺酸酯或苄基碘处理吡啶基-5-氨基噻唑（1-4）可得到相应的吡啶鎓5-氨基噻唑（5-10），相对于1-4，吡啶鎓显示出红移的吸收光谱和荧光光谱。此外，通过粉末X射线衍射分析检查了5种特定于卤化溶剂的蒸气致变色性质。因此，包含5的Pmma膜可用于检测卤化溶剂，尤其是CH 2 Cl 2。
• 5-Amino-2-thiazolylpyridine N-Oxides: Synthesis and Properties
  作者：Toshiaki Murai、Yuuta Nakatsu、Yuki Tsuchiya、Kirara Yamaguchi、Toshifumi Maruyama、Yohei Miwa、Shoichi Kutsumizu

  DOI：10.3987/com-19-s(f)51

  日期：——

  5-Amino-2-thiazolylpyridine N-oxides were prepared in low to moderate yields by the oxidation of 2-pyridyl-5-aminothiazoles with m-CPBA. The molecular structures of the resulting N-oxides were unequivocally determined by X-ray analyses. The N-oxides exhibited the absorption maxima at around 415 +/- 20 nm in a CHCl3 solution, while the emission spectra were observed in the range of 505 to 604 nm. The red -shift of the emission was attributed to the methoxy groups attached to the para-position of an aromatic group on the nitrogen atom at the 5-position. The N-oxides exhibited halochromism with the addition of B(C6F5)(3). The change in absorption implied the formation of a 1:1 complex between N-oxide and B(C6F5)(3). The emission wavelengths of the N-oxides were observed at 510 +/- 25 nm in a solid state. Interestingly, one of the N-oxides having methoxy groups exhibited mechanofluorochromism. The solid-state emission of the N-oxide at 527 nm shifted to a longer wavelength (599 nm) when it was subjected to grinding.