5-phenyl-2-(pyridin-2-yl)-1,3-thiazol-4-ol | 1233941-64-4

• 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-phenyl-2-(pyridin-2-yl)-1,3-thiazol-4-ol
• 英文别名: 5-phenyl-2-(pyridin-2-yl)thiazol-4-ol；5-Phenyl-2-pyridin-2-yl-1,3-thiazol-4-ol；5-phenyl-2-pyridin-2-yl-1,3-thiazol-4-ol
• CAS: 1233941-64-4
• 化学式: C₁₄H₁₀N₂OS
• 分子量: 254.312
• InChiKey: YHASSGHSOZHPAN-UHFFFAOYSA-N

物化性质

• 沸点：
  469.1±53.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-phenyl-2-(pyridin-2-yl)-1,3-thiazol-4-ol 在 氯磺酸 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.25h， 生成 4-(4-(3-chloropropoxy)-2-(pyridin-2-yl)thiazol-5-yl)-N,N-diethylbenzenesulfonamide
  参考文献：
  名称：

  Tuning the polarity and surface activity of hydroxythiazoles – extending the applicability of highly fluorescent self-assembling chromophores to supra-molecular photonic structures

  摘要：

  通过Langmuir-Blodgett技术处理4-烷氧基噻唑磺胺类化合物，揭示了聚集对薄膜电光性能的影响。

  DOI：

  10.1039/c5tc03632a
• 作为产物：
  描述：

  吡啶-2-羧硫酸胺 、 α-溴苯乙酸乙酯 生成 5-phenyl-2-(pyridin-2-yl)-1,3-thiazol-4-ol
  参考文献：
  名称：

  Tuning the polarity and surface activity of hydroxythiazoles – extending the applicability of highly fluorescent self-assembling chromophores to supra-molecular photonic structures

  摘要：

  通过Langmuir-Blodgett技术处理4-烷氧基噻唑磺胺类化合物，揭示了聚集对薄膜电光性能的影响。

  DOI：

  10.1039/c5tc03632a

文献信息

• Synthesis and Characterization of New 4-Hydroxy-1,3-thiazoles
  作者：Dieter Weiß、Rainer Beckert、Eric Täuscher、Helmar Görls

  DOI：10.1055/s-0029-1219759

  日期：2010.5

  A series of highly substituted 4-hydroxy-1,3-thiazoles was synthesised in two different ways. Whereas their anions display strong fluorescence in the bathochromic part of the visible spectrum, the emission is shifted hypsochromically upon alkylation reactions. This easy switch between the anion and its derivatives makes them suitable for widespread applications. The thiazoles possess prerequisites for the complexation of metals due to the coexistence of aza-heterocycles and of 1,3-diketone substructures. In addition, the hydroxy group allows further functionalisation reactions, as exemplified by the incorporation of an azide or an acetylene into the product, and by the synthesis of a star-shaped derivative.

  一系列高度取代的4-羟基-1,3-噻唑通过两种不同的方法合成。尽管它们的阴离子在可见光的长波部分呈现出强烈的荧光，但在烷基化反应过程中，发射波长却向短波方向偏移。这种阴离子与其衍生物之间的轻松转换使其适用于广泛的应用。噻唑类化合物由于同时存在氮杂环和1,3-二酮子结构，具备了与金属络合的前提条件。此外，羟基的存在允许进一步的功能化反应，例如将叠氮基或炔基引入产物中，以及合成星形衍生物。
• The Combination of 4-Hydroxythiazoles with Azaheterocycles: Efficient Bidentate Ligands for Novel Ruthenium Complexes
  作者：Roberto Menzel、Eric Täuscher、Dieter Weiß、Rainer Beckert、Helmar Görls

  DOI：10.1002/zaac.200900523

  日期：——

  of three novel ligands, in which an azaheterocycle is connected with a thiazole subunit: 4-methoxy-5-methyl-2-pyridine-2-yl-1,3-thiazole (1), 4-methoxy-5-methyl-2-pyrimidine-2-yl-1,3-thiazole (2) and 4-methoxy-5-phenyl-2-pyridine-2-yl-1,3-thiazole (3) are reported. Because these ligands are cyclic versions of 1,4-diazadienes, they offer good prerequisites for the synthesis of metal complexes and were

  在此合成了三个新型配体，其中氮杂杂环与噻唑亚基相连：4-甲氧基-5-甲基-2-吡啶-2-基-1,3-噻唑 (1), 4-甲氧基-5-报道了甲基-2-嘧啶-2-基-1,3-噻唑 (2) 和 4-甲氧基-5-苯基-2-吡啶-2-基-1,3-噻唑 (3)。由于这些配体是 1,4-二氮杂二烯的环状形式，它们为金属配合物的合成提供了良好的先决条件，并被用作螯合配体。成功合成了三种新型的 Ru(bpy)2(L) 型杂配阳离子配合物，bpy = 2,2'-联吡啶。RuII配合物以及配体通过质谱、NMR、UV/Vis和IR光谱以及元素分析来表征。此外，Ru(bpy)22(PF6)的X射线结构，
• Hydroxythiazole-Based Fluorescent Probes for Fluoride Ion Detection
  作者：Lorena K. Calderón-Ortiz、Eric Täuscher、Erick Leite Bastos、Helmar Görls、Dieter Weiß、Rainer Beckert

  DOI：10.1002/ejoc.201200140

  日期：2012.5

  their use as fast-response “turn-on” probes for fluoride ion detection in polar aprotic solvents and in aqueous cetyltrimethylammonium bromide micellar medium. The fluoride-triggered deprotection of these silyl ethers results in ca. 180-nm shifts in the fluorescence emission wavelengths. All compounds are suitable for the detection of fluoride ions with a detection limit in DMSO of 10–7 mol L–1; derivatives

  这项工作描述了五种 O-甲硅烷氧基-1,3-噻唑的合成及其作为快速响应“开启”探针在极性非质子溶剂和十六烷基三甲基溴化铵胶束介质中检测氟离子的用途。这些甲硅烷基醚的氟化物触发脱保护导致约。荧光发射波长偏移 180 nm。所有化合物都适用于检测氟离子，在 DMSO 中的检测限为 10-7 mol L-1；在噻唑系统中含有 2-吡啶基部分的衍生物比含有 3- 或 4-吡啶基部分的衍生物更有效。O-甲硅烷氧基-1,3-噻唑无法检测到典型的阴离子干扰物，例如醋酸盐或氯化物，因此这些化合物对氟化物非常具有特异性。
• Synthesis and Resonance Energy Transfer Study on a Random Terpolymer Containing a 2-(Pyridine-2-yl)thiazole Donor-Type Ligand and a Luminescent [Ru(bpy)₂(2-(triazol-4-yl)pyridine)]²⁺ Chromophore
  作者：Bobby Happ、Johann Schäfer、Roberto Menzel、Martin D. Hager、Andreas Winter、Jürgen Popp、Rainer Beckert、Benjamin Dietzek、Ulrich S. Schubert

  DOI：10.1021/ma201193e

  日期：2011.8.23

  A statistical terpolymer, containing a 2-(pyridine-2-yl)-1,3-thiazole donor-type system and an acceptor-type [Ru(bpy)(2)(2-(triazol-4-yl)pyridine)](2+) chromophore as well as methyl methacrylate as comonomer, was synthesized using the controlled reversible addition-fragmentation chain transfer polymerization (RAFT) approach. Additionally, the appropriate donor- and acceptor-type copolymers were synthesized, whereas only a maximum content of 5 mol % of the ruthenium(II) chromophore could be incorporated into the macromolecules caused by its nitro-functionalization. The resulting terpolymer exhibited a direct Forster resonance energy transfer from the thiazole to the ruthenium(II) subunit as indicated by emission spectroscopy of the Ru(II) phosphorescence as well as lifetime measurements and quantum yield determinations of the thiazole fluorescence. The efficiency of the energy transfer was found to be higher than 70%.