1,2-bis(2'-pyridylethynyl)benzene | 350587-04-1

• 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: 1,2-bis(2'-pyridylethynyl)benzene
• 英文别名: 1,2-bis(pyridin-2-ylethynyl)benzene；Benzene, 1,2-bis(2-pyridin-2-ylethynyl)-；2-[2-[2-(2-pyridin-2-ylethynyl)phenyl]ethynyl]pyridine
• CAS: 350587-04-1
• 化学式: C₂₀H₁₂N₂
• 分子量: 280.329
• InChiKey: FNUCEKUSUXIHOK-UHFFFAOYSA-N

物化性质

• 熔点：
  113 °C
• 沸点：
  501.6±35.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-bis(2'-pyridylethynyl)benzene 以 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 生成 dibromo-(1,2-bis((2-pyridyl)ethynyl)benzene)palladium
  参考文献：
  名称：

  具有由两个吡啶基和刚性π-共轭主链组成的反式螯合配体的Pd配合物

  摘要：

  摘要由1,2-二碘苯与2-炔基吡啶的1：2 Sonogashira反应制备了具有两个吡啶基和π共轭骨架的1,2-双（2-吡啶基乙炔基）苯衍生物。所获得的配体与钯（II）配合物如[PdCl 2（cod）]和[PdCl 2（MeCN）2]反应，形成具有以反螯合双齿模式配位的配体的配合物。由1，3-二碘苯和2-炔基吡啶获得的配体桥接两个Pd（II）中心，生成二铝配合物。具有反式螯合配体的二氯钯配合物在中心亚芳基中含有两个甲氧基，可促进苯基锂和苯基乙炔的偶联，从而产生各自的均偶联产物。

  DOI：

  10.1016/j.poly.2012.04.006
• 作为产物：
  描述：

  1,2-二碘苯 在 四(三苯基膦)钯 copper(l) iodide 、 potassium carbonate 、 正丁胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 6.0h， 生成 1,2-bis(2'-pyridylethynyl)benzene
  参考文献：
  名称：

  Cytotoxicities, cell cycle and caspase evaluations of 1,6-diaryl-3(Z)-hexen-1,5-diynes, 2-(6-aryl-3(Z)-hexen-1,5-diynyl)anilines and their derivatives

  摘要：

  Compounds 3, 6-7, 9-10, 15-17, and 20-21 showed growth inhibition effects on a full panel of 60 human cancer cell lines, and most of the average IC50 values of the indicated analogues were from < 0.01 to 96.6 mu M, in which analogues 16 and 17 revealed the highest cytotoxic activity with the cancer cell lines at 10(-7) M concentration range. During the cell cycle analysis, a moderate to high apoptotic progress induction was shown by 3, 9, 16-17, and 20 compared with the control, which 2-(6-(2-thienyl)-3(Z)-hexen-1,5-diynyl)aniline 16 showed the highest apoptotic effect. Structures 16-17 displayed a significant G2/M phase arrest in the cell growth cycle compared with other derivatives, which the proportions of the G2/M phase cells were accumulated to 71.5% and 82.6%, respectively. Moreover, the colorimetric assay of 16-17 also provided advanced evidence to the relationship between the compounds and the caspase-3 enzyme, which was one of the major promoters of apoptotic effect. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.062

文献信息

• Self-Assembly and Substituent Effect of Copper(I) Complexes with 1,2-Bis(2-pyridylethynyl)benzene Ligands
  作者：Tomikazu Kawano、Jun Kuwana、Ikuo Ueda

  DOI：10.1246/bcsj.76.789

  日期：2003.4

  The reaction of 1,2-bis(2-pyridylethynyl)benzenes (L1–L5) with copper(I) ions proceeded smoothly to afford mononuclear copper(I) chelate complexes CL1–CL3 or dinuclear copper(I) molecular rectangular boxes, CL4 and CL5, in excellent yields, depending on the size of the substituent. If a ligand with a small substituent was used, the self-assembly of a mononuclear copper(I) chelate complex was achieved. If a ligand with a bulky substituent was used, the self-assembly of dinuclear copper(I) molecular rectangular boxes was achieved. The equilibrium between these two copper(I) complexes was also observed in solution.

  1,2-双(2-吡啶乙炔基)苯(L1–L5)与铜(I)离子的反应顺利进行，根据取代基的大小，以优异的产率得到了单核铜(I)螯合配合物CL1–CL3或双核铜(I)分子矩形盒CL4和CL5。如果使用具有小取代基的配体，则实现了单核铜(I)螯合配合物的自组装。如果使用具有大取代基的配体，则实现了双核铜(I)分子矩形盒的自组装。这两种铜(I)配合物之间的平衡在溶液中也有所观察。
• Copper-free Sonogashira Coupling Reaction Using a<i>trans</i>-Spanning 1,2-Bis(2-thienylethynyl)benzene Ligand
  作者：Shingo Atobe、Motohiro Sonoda、Yuki Suzuki、Hiroyuki Shinohara、Takuya Yamamoto、Akiya Ogawa

  DOI：10.1246/cl.2011.925

  日期：2011.9.5

  Novel copper-free Sonogashira coupling reaction of aryl halides with terminal acetylenes proceeded in the presence of 1,2-bis(2-thienylethynyl)benzene (1) as a trans-bidentatable ligand.

  芳基卤化物与末端乙炔的新型无铜 Sonogashira 偶联反应在 1,2-双（2-噻吩基乙炔基）苯 (1) 作为可反式双齿配体的存在下进行。
• Palladium-catalyzed oxidative homocoupling reaction of terminal acetylenes using trans-bidentatable 1-(2-pyridylethynyl)-2-(2-thienylethynyl)benzene
  作者：Shingo Atobe、Motohiro Sonoda、Yuki Suzuki、Takuya Yamamoto、Haruna Masuno、Hiroyuki Shinohara、Akiya Ogawa

  DOI：10.1007/s11164-012-0654-2

  日期：2013.1

  Palladium-catalyzed oxidative homocoupling of terminal acetylenes, in air, occurred in the presence of 1-(2-pyridylethynyl)-2-(2-thienylethynyl)benzene as ligand, affording the corresponding conjugated diynes.

  在存在1-（2-吡啶基乙炔基）-2-（2-噻吩基乙炔基）苯作为配体的情况下，钯催化的末端乙炔在空气中的氧化均偶联发生，得到相应的共轭二炔。
• Symmetric Halogen Bonding Is Preferred in Solution
  作者：Anna-Carin C. Carlsson、Jürgen Gräfenstein、Adnan Budnjo、Jesse L. Laurila、Jonas Bergquist、Alavi Karim、Roland Kleinmaier、Ulrika Brath、Máté Erdélyi

  DOI：10.1021/ja301341h

  日期：2012.3.28

  Halogen bonding is a recently rediscovered secondary interaction that shows potential to become a complementary molecular tool to hydrogen bonding in rational drug design and in material sciences. Whereas hydrogen bond symmetry has been the subject of systematic studies for decades, the understanding of the analogous three-center halogen bonds is yet in its infancy. The isotopic perturbation of equilibrium

  卤素键是最近重新发现的二次相互作用，显示出成为合理药物设计和材料科学中氢键的补充分子工具的潜力。尽管氢键对称性几十年来一直是系统研究的主题，但对类似的三中心卤素键的理解仍处于起步阶段。将同位素扰动平衡 (IPE) 技术与 (13) C NMR 检测应用于区域选择性氘化吡啶配合物，以研究溶液中 [NIN](+) 和 [N-Br-N](+) 卤素键的对称性。对于可自由调节的和构象受限的 [NXN](+) 模型系统，观察到对对称排列的偏好，这也通过 DFT 级别的计算得到证实。紧密连接的抗衡离子显示出与优选的对称排列相容。实验观察和计算预测表明，在形成对称的三中心四电子卤素键时，能量增益很高。虽然氢键在溶液中通常是不对称的而在结晶状态下是对称的，但类似的以溴和碘为中心的卤素键在溶液中更喜欢对称排列。
• Aerobic Cu-catalyzed oxidative 1 : 2 coupling of benzynes with terminal alkynes
  作者：Tianhao Lu、Yong Shen、Min Wang、Zibing Zhang、Shijun Li、Chunsong Xie

  DOI：10.1039/d0cc03150j

  日期：——

  Cu-Catalyzed oxidative 1 : 2 couplings of arynes with nucleophilic terminal alkynes under aerobic conditions are described herein. A mechanistic investigation revealed a plausible involvement of an aryl-Cu(III)-generating pathway. By this method, ubiquitous arenediynes can be efficiently assembled in a single step under mild conditions.

  本文描述了在有氧条件下，芳烃与亲核末端炔烃的Cu催化的氧化1：2偶联。一项机械调查显示，可能发生了芳基-铜（III）生成途径。通过这种方法，可以在温和的条件下一步完成无处不在的芳烃。