4-(2-(2-pyridinyl)ethenyl)phenol | 1209-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-(2-pyridinyl)ethenyl)phenol
• 英文别名: 4-Hydroxystyrylpyridine；4-(2-pyridin-2-ylethenyl)phenol
• CAS: 1209-03-6
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: ZOSLIBAXJLWTFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-(2-pyridinyl)ethenyl)phenol 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 t-butyl 4-(6-(4-(2-(2-pyridinyl)vinyl)phenoxy)hexyloxy)phenylcarbamate
  参考文献：
  名称：

  Comparative Syntheses of Arylamine Monomer with Styrylpyridyl Photo-Crosslinker of Polyarylamine for OLED Hole-Injection Material

  摘要：

  A new arylamine monomer with photo-crosslinkable styrylpyridinyl moiety of conjugated polyarylamine for OLED hole injection material was synthesized through two synthetic routes, BOC-amine protection/deprotection and nitro group reduction methods. Both synthetic routes yielded practically pure amine product by standard aqueous workup and crystallization in 61% overall yield from pyridinylvinylphenol 2. Their reaction efficiencies were comparatively studied in views of practicality and reaction scale. Also, the synthetic conditions of key compound of photo-crosslinker, pyridinylvinylphenol 2 was reinvestigated and established for the reproducible and reliable preparation.

  DOI：

  10.1080/15421406.2010.499316
• 作为产物：
  描述：

  4-(2-(2-pyridinyl)ethenyl)phenyl acetate 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以92%的产率得到4-(2-(2-pyridinyl)ethenyl)phenol
  参考文献：
  名称：

  发现新的基于吡啶啉酰胺的衍生物作为新型VEGFR-2激酶抑制剂：合成，体外生物学评估和分子对接†

  摘要：

  血管内皮生长因子受体2（VEGFR-2）在肿瘤血管生成中起着至关重要的作用，而对VEGFR-2信号通路的抑制已成为癌症治疗的诱人靶标。在我们的努力中，设计并合成了一系列新的基于吡啶啉酰胺的衍生物，它们是有效且有效的VEGFR-2抑制剂。在体外评估所有新制备的化合物对A549和HepG2细胞系的抗增殖活性。在新化合物中，8j和8l对A549和HepG2细胞系均表现出更好的活性。进行分子对接以研究与VEGFR-2（PDB代码：4ASD）的结合能力和结合方式。

  DOI：

  10.1039/c8md00057c

文献信息

• Discovery of novel picolinamide-based derivatives as novel VEGFR-2 kinase inhibitors: synthesis,<i>in vitro</i>biological evaluation and molecular docking
  作者：Wuji Sun、Shubiao Fang、Hong Yan

  DOI：10.1039/c8md00057c

  日期：——

  Vascular endothelial growth factor receptor-2 (VEGFR-2) plays a crucial role in tumor angiogenesis, and inhibition of the VEGFR-2 signaling pathway has emerged as an attractive target for cancer therapy. In our effort, a novel series of picolinamide-based derivatives were designed and synthesized as potent and effective VEGFR-2 inhibitors. All the newly prepared compounds were evaluated in vitro for

  血管内皮生长因子受体2（VEGFR-2）在肿瘤血管生成中起着至关重要的作用，而对VEGFR-2信号通路的抑制已成为癌症治疗的诱人靶标。在我们的努力中，设计并合成了一系列新的基于吡啶啉酰胺的衍生物，它们是有效且有效的VEGFR-2抑制剂。在体外评估所有新制备的化合物对A549和HepG2细胞系的抗增殖活性。在新化合物中，8j和8l对A549和HepG2细胞系均表现出更好的活性。进行分子对接以研究与VEGFR-2（PDB代码：4ASD）的结合能力和结合方式。
• Visible-light TiO₂-catalyzed synthesis of dihydrobenzofurans by oxidative [3 + 2] annulation of phenols with alkenyl phenols
  作者：Jingze Wu、Yaning Liu、Marisa C. Kozlowski

  DOI：10.1039/d4sc00723a

  日期：——

  selectively captured by a neutral phenol nucleophile, rendering β-5′ coupling with excellent chemo- and regio-selectivity. The reaction proceeds under benign conditions, using an inexpensive, nontoxic, and recyclable photocatalyst under visible light irradiation with air as the terminal oxidant at room temperature.

  报道了通过非均相光催化制备二氢苯并呋喃的氧化策略。该方法利用烯基苯酚和TiO 2固体表面之间的表面相互作用，从而能够通过可见光直接激活，而不需要预功能化或表面改性。由此产生的烯基苯氧基自由基被中性苯酚亲核试剂选择性捕获，使 β-5' 偶联具有优异的化学和区域选择性。该反应在良性条件下进行，使用廉价、无毒且可回收的光催化剂，在可见光照射下，以空气作为终端氧化剂，在室温下进行。
• Synthesis of New Conjugated Polymers as Hole Injection Layer and Performance of OLED Devices
  作者：Tae Wook Yoo、Chul Park、Nguyen Thi Mai、Dong Uk Kim、Lee Soon Park

  DOI：10.1080/15421406.2011.600145

  日期：2011.11.4

  The fluorene-based poly(dioctylfluorene-alt-biphenylamine)s with styrylpyridyl group were synthesized by using Pd-catalyzed polycondensation reaction. These hole injection/transport polymers showed very good solvent resistance after photo-crosslinking which could facilitate the subsequent spin coating of the emitting layer polymer solution. Moreover these polymers could be patterned by using distyrylpyridyl alkyl monomer (DSM) as crosslinking agents. The OLED devices with configuration of ITO/HIL/Alq(3):NPD/LiF/Al in which synthesized polymer was used as hole injection layer (HIL) were fabricated and their performance was compared with the commercially available PEDOT:PSS as HIL layer.
• Synthesis and Photolithographic Property of Conjugated Polymers with Polyazomethine Structure
  作者：Sang Chul Ryu、Young Chul Jeong、Lee Soon Park

  DOI：10.1080/15421400903240803

  日期：2009.11.11

  Two different polyazomethine-type conjugated polymers, poly(phenoxiazine-3, 3'-dihydroxybensidine)(PZ-DHB) and poly(phenoxiazine-2,4-diamino-6-hydroxypyrimidine)(PZ-DHP) containing phenothiazine moiety and azomethine linkage in the main chain were synthesized by Schiff-base polycondensation reactions. The polymer poly(PZ-DHB) was converted to the photosensitive type, through Mitsunobu reaction by incorporation of a photocrosslinkable group, hydroxyhexyloxystyryl-2-pyridine(2-HHSP) into the polymer side chains. The photosensitive conjugated polymer, poly(PZ-DHB)-PS, exhibited both strong fluorescence emission at 555 nm and good patterning property in the standard photolithographic processes.
• Design, synthesis and biological evaluation of pyrimidine-based derivatives as VEGFR-2 tyrosine kinase inhibitors
  作者：Wuji Sun、Shengquan Hu、Shubiao Fang、Hong Yan

  DOI：10.1016/j.bioorg.2018.04.005

  日期：2018.8

  of the VEGFR-2 signaling pathway has already become an attractive approach for cancer therapy. In this study, a novel pyrimidine-based derivative 7j was designed as lead compound, and three series of potent VEGFR-2 inhibitors were synthesized and biologically evaluated against A549 and HepG2 cell lines. Compounds 7d, 9s and 13n exhibited superior inhibitory activities against A549 cell with IC50 ranged

  血管内皮生长因子受体2（VEGFR-2）在肿瘤血管生成中起着至关重要的作用，而抑制VEGFR-2信号通路已经成为癌症治疗的一种有吸引力的方法。在这项研究中，设计了一种新型的基于嘧啶的衍生物7j作为前导化合物，合成了三组有效的VEGFR-2抑制剂，并针对A549和HepG2细胞系进行了生物学评估。与Pazopanib（IC 50）相比，化合物7d，9s和13n对A549细胞的IC 50为9.19至13.17μM，对HepG2细胞的IC 50为11.94至18.21μM。 = 21.18和36.66μM）。另外，进行了分子对接研究以研究目标化合物与VEGFR-2之间的结合能力和结合方式。