1-amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-thione | 121019-47-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-thione
• 英文别名: (1-amino-4-phenyl-2-sulfanylidenepyrimidin-5-yl)-phenylmethanone
• CAS: 121019-47-4
• 化学式: C₁₇H₁₃N₃OS
• 分子量: 307.376
• InChiKey: LJXUZXORYKMBSM-UHFFFAOYSA-N

物化性质

• 熔点：
  195 °C(Solv: ethanol (64-17-5))
• 沸点：
  474.8±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-thione 在 盐酸 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以46%的产率得到5-benzoyl-4-phenyl-1H-pyrimidine-2(H)-thione
  参考文献：
  名称：

  Reactions of cyclic oxalyl compounds, Part 30: Some reactions with N-amino-pyrimidine derivatives

  摘要：

  DOI：

  10.1007/bf00809772
• 作为产物：
  描述：

  4-benzoyl-5-phenyl-furan-2,3-dione 以 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 2.21h， 生成 1-amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-thione
  参考文献：
  名称：

  Akcamur, Yunus; Altural, Behzat; Saripinar, Emin, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1419 - 1422

  摘要：

  DOI：

文献信息

• Synthesis and Characterization of Diazenyl-1,3-diphenylpropane-1,3-dione and 5-[Hydroxy(phenyl)methyl]-4-phenylpyrimidine Derivatives
  作者：Zülbiye Önal、Ayhan Özalp、Ilhan Özer Ilhan、Güzin Aslan

  DOI：10.14233/ajchem.2014.17461

  日期：——

  Various novel diazenyl-1,3-diphenylpropane-1,3-dione derivatives (2a-f) were prepared by the condensation of the diazonium salts of N-aminopyrimidine derivatives with b-diketones. Also, a series of novel 5-[hydroxy(phenyl)methyl]-4-phenylpyrimidine derivatives (3a-f) were synthesized from the reduction reactions of N-aminopyrimidine derivatives with NaBH4. The structures of all the new synthesized compounds were characterized by the 13C-NMR, 1H-NMR and IR spectroscopic data and elemental analysis.

  通过N-氨基嘧啶衍生物的重复盐与β-二酮的缩合反应,制备了多种新型二氮烯基-1,3-二苯基丙烷-1,3-二酮衍生物(2a-f)。同时,通过N-氨基嘧啶衍生物与NaBH4的还原反应,合成了一系列新型5-[羟基(苯基)甲基]-4-苯基嘧啶衍生物(3a-f)。所有新合成化合物的结构均通过13C-NMR、1H-NMR、IR光谱数据和元素分析进行了表征。
• Synthesis, characterization, biological studies, and molecular modeling of mixed ligand bivalent metal complexes of Schiff bases based on $N$-aminopyrimidine-2-one/2-thione
  作者：Hatice Gamze SOĞUKÖMEROĞULLARI、Tuğba TAŞKIN TOK、Feyza YILMAZ、İsmet BERBER、Mehmet SÖNMEZ

  DOI：10.3906/kim-1412-81

  日期：——

  New mixed Schiff bases, Cu(II), Co(II), Ni(II), and Mn(II) complexes, were synthesized derived from 5-chloro-2-hydroxyacethophenone and 1-amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-one/thione. These complexes were characterized by elemental analysis, magnetic measurements, molar conductivity, IR, electronic, NMR, and mass spectral studies. All the complexes showed nonelectrolytic behavior. Moreover, the newly synthesized mixed ligand complexes were evaluated for their in vitro antimicrobial efficiency against bacteria and yeast. The compound named Co(L$_1}$L) had good antifungal activity against Candida species, but no profound antibacterial effect against bacterial strains. In addition, the ground state geometries of the complexes were optimized using a semi-empirical method at PM6 level, which is a suitable and effective basis set for organometallic and large structures to obtain information about their 3D geometries and electronic structures.

  由 5-氯-2-羟基苯乙酮和 1-氨基-5-苯甲酰基-4-苯基-1H-嘧啶-2-酮/硫酮合成了新的混合希夫碱、铜(II)、钴(II)、镍(II)和锰(II)配合物。通过元素分析、磁性测量、摩尔电导率、红外光谱、电子显微镜、核磁共振和质谱研究对这些复合物进行了表征。所有配合物均表现出非电解行为。此外，还对新合成的混合配体复合物进行了体外抗细菌和酵母菌效率的评估。被命名为 Co(L$_1}$L) 的化合物对白色念珠菌具有良好的抗真菌活性，但对细菌菌株没有明显的抗菌效果。此外，研究人员还采用 PM6 水平的半经验方法优化了这些复合物的基态几何结构。PM6 水平是有机金属和大型结构的一个合适而有效的基集，可以获得它们的三维几何结构和电子结构信息。
• Synthesis, Characterisation and Antimicrobial Activity 1-Aminopyrimidine-2(1H)-Thione and its Co(II), Ni(II), Pd(II) and Pt(II) Complexes
  作者：Mehmet Gülcan、Mehmet Sönmez

  DOI：10.3184/030823410x12743665489527

  日期：2010.5

  Metal complexes of 1-aminopyrimidine-2(1H)-thione were prepared from acetate salts of Co(II), Ni(II), Pd(II) and Pt(II) in methanol. Electronic spectral data and magnetic moment measurements suggest mononuclear square planar geometrical structures for the metal complexes. The ligand and all the metal complexes were evaluated for their antimicrobial activity. The newly synthesised ligand and the Co(II) complex showed moderate activity against all tested bacteria and yeast strains.

  以甲醇中 Co(II)、Ni(II)、Pd(II) 和 Pt(II) 的醋酸盐为原料，制备了 1-氨基嘧啶-2(1H)-硫酮的金属配合物。电子光谱数据和磁矩测量结果表明，这些金属配合物具有单核方形平面几何结构。对配体和所有金属配合物的抗菌活性进行了评估。新合成的配体和 Co(II) 复合物对所有测试的细菌和酵母菌株都显示出中等程度的活性。
• Nitrogen Oxygen Bonded Heterocyclic Organotin (IV) Derivatives of a New Schiff Base: Synthesis and Spectral Aspects
  作者：Medepalli David Raju

  DOI：10.1515/mgmc.2010.33.1-2.1

  日期：2010.1

  Some di, tri-organosilicon (IV) metal complexes of a new SNO tridentate heterocyclic Schiff base derived from the reaction of 1-amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-thione with salicylaldehyde have been synthesized and characterized on the basis of elemental analyses, IR, 1 H, 13 C, 29 Si NMR spectra, It has been found that the Schiff base behaves as a neutral tridentate SNO ligand forming chelates

  合成并表征了一些由 1-氨基-5-苯甲酰基-4-苯基-1H-嘧啶-2-硫酮与水杨醛反应衍生的新型 SNO 三齿杂环席夫碱的二、三有机硅 (IV) 金属配合物根据元素分析、IR、 1 H、 13 C、 29 Si NMR 光谱，已发现席夫碱表现为中性三齿 SNO 配体，与 1 : 2 和 1 : 1（金属：配体）形成螯合物化学计量。
• 2, 6-Bis((<i>E</i>)-((5-benzoyl-2-thioxo-4-phenylpyrimidin-1(<i>2H</i>)-yl)imino)methyl)-4-(methyl)phenol and its Metal(II) Complexes: Synthesis, Spectroscopy, Biological Activity, and Photoluminescence Features
  作者：Mehmet Gulcan、Hüseyin Zengin、Metin Çelebi、Mehmet Sönmez、İsmet Berber

  DOI：10.1002/zaac.201300224

  日期：2013.10

  The photoluminescence quantum yields and long excited-state lifetimes of the ligand and its complexes were calculated as 42 % and 3.94 ns, respectively. The photoluminescence intensities and quantum yields of metal complexes changed upon complexation with various metal ions. The ligand and its complexes are of interest as organic emitting materials for electroluminescent devices. The complexes were

  多种金属配合物的制备、表征、磁性测量、抗菌活性和光致发光特性，这些配合物具有源自 2, 6-diformyl-4-methylphenol 和 1-amino-5-benzoyl-4-phenyl-1H 的 Schiff 碱配体-嘧啶-2-硫酮在本文中报道。UV/Vis 光谱和磁性测量推断出 PdII 和 PtII 配合物的方形平面立体化学，以及其他金属配合物的八面体排列。这些化合物在紫外线照射下会产生强烈的发射（其中 λmax = 402 nm）。配体及其配合物的光致发光量子产率和长激发态寿命分别计算为 42% 和 3.94 ns。金属络合物的光致发光强度和量子产率在与各种金属离子络合后发生变化。配体及其配合物作为用于电致发光器件的有机发光材料是令人感兴趣的。此外还评估了复合物对细菌和真菌菌株的体外抗微生物活性。虽然 CuII、CoII 和 PtII 复合物对酵母菌具有良好的抗真菌效率（MICs，80