N-(phenylmethyl)-4-pyridinecarbothioamide | 109847-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(phenylmethyl)-4-pyridinecarbothioamide
• 英文别名: N-benzylpyridine-4-carbothioamide；thioisonicotinic acid benzylamide；Thioisonicotinsaeure-benzylamid
• CAS: 109847-20-3
• 化学式: C₁₃H₁₂N₂S
• 分子量: 228.318
• InChiKey: MABNIUROCJYZPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  24.92
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(phenylmethyl)-4-pyridinecarbothioamide 在 碘 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 72.0h， 生成
  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：

  异烟酸 在 tetraphosphorus decasulfide 、 xylene 作用下， 生成 N-(phenylmethyl)-4-pyridinecarbothioamide
  参考文献：
  名称：

  Libermann et al., Bulletin de la Societe Chimique de France, 1958, p. 687,691

  摘要：

  DOI：

文献信息

• <i>N</i>,<i>N</i>-Diarylthiazol-5-amines: Structure-Specific Mechanofluorochromism and White Light Emission in the Solid State
  作者：Yuki Tsuchiya、Kirara Yamaguchi、Yohei Miwa、Shoichi Kutsumizu、Mao Minoura、Toshiaki Murai

  DOI：10.1246/bcsj.20200083

  日期：2020.7.15

  A range of N,N-diarylthiazol-5-amines having a 4-pyridyl group on a thiazole ring were developed, and their photophysical properties were elucidated. Their synthesis was achieved by applying our methods to the combination of N-arylmethyl secondary thioamides and N,N-diarylthioformamides. This enabled us to obtain amines with different types of aromatic groups on the nitrogen atom. Their absorption and emission spectra in solution were examined. The 4-pyridyl group gives higher polarity to the amines. The solid-state emissions of the amines were also evaluated. Several amines showed mechanofluorochromism (MFC). A 4-pyridyl group on a thiazole ring was a requisite for the expression of MFC properties. Although N-(5-thiazolyl) N,N-di(2-naphthyl)amines did not exhibit MFC by grinding of the pristine powder, white-light emission was observed when the ground powder was fumed with acetone vapor.

  摘要 开发了一系列在噻唑环上具有 4-吡啶基的 N,N-二芳基噻唑-5-胺，并阐明了它们的光物理特性。它们的合成是通过将我们的方法应用于 N-芳基甲基仲硫酰胺和 N,N-二芳基硫代甲酰胺的组合而实现的。这使我们获得了在氮原子上带有不同类型芳香基团的胺。我们研究了它们在溶液中的吸收和发射光谱。4 吡啶基赋予胺更高的极性。此外，还对这些胺的固态发射进行了评估。有几种胺显示出机械氟变色（MFC）。噻唑环上的 4-吡啶基是表现 MFC 特性的必要条件。虽然通过研磨原始粉末，N-(5-噻唑基) N,N-二(2-萘基)胺并没有显示出 MFC，但当研磨粉末与丙酮蒸气熏蒸时，却观察到了白光发射。
• 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
• Koenig et al., Chemische Berichte, 1954, vol. 87, p. 825,834
  作者：Koenig et al.

  DOI：——

  日期：——