6,6'-bis-(phenylethynyl)-2,2'-bipyridine | 136413-50-8

• 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: 6,6'-bis-(phenylethynyl)-2,2'-bipyridine
• 英文别名: 6,6'-bis(phenylethynyl)-2,2'-bipyridine；2-(2-Phenylethynyl)-6-[6-(2-phenylethynyl)pyridin-2-yl]pyridine
• CAS: 136413-50-8
• 化学式: C₂₆H₁₆N₂
• 分子量: 356.426
• InChiKey: MTRGDQQWORYBRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• 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

• 作为产物：
  描述：

  2,6-二溴吡啶 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 作用下， 以 三乙胺 为溶剂， 反应 0.5h， 生成 6,6'-bis-(phenylethynyl)-2,2'-bipyridine
  参考文献：
  名称：

  Butler, Ian; Soucy-Breau, Chantal, Canadian Journal of Chemistry, 1991, vol. 69, # 7, p. 1117 - 1123

  摘要：

  DOI：
• 作为试剂：
  描述：

  heptadeca-1,2-diene 、 苯硅烷 在 三乙基硼氢化钠 、 6,6'-bis-(phenylethynyl)-2,2'-bipyridine 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以60%的产率得到(heptadec-1-en-3-yl)(phenyl)silane
  参考文献：
  名称：

  An Efficient Route to Branched Allylsilanes through Copper-Catalyzed Allene Hydrosilylation Using Readily Available Silanes

  摘要：

  摘要 开发了一种CuCl催化的烯烃与PhSiH3的氢硅化反应。这是首个使用易得的廉价硅烷试剂在铜催化的烯烃氢硅化中生成支链烯丙基硅烷的例子。这种基础金属催化剂提供了一种原子经济且高效的方法，可以获得具有优异区域选择性的支链烯丙基硅烷。

  DOI：

  10.1055/a-1829-8574

文献信息

• Conjugated Microporous Polymer as Heterogeneous Ligand for Highly Selective Oxidative Heck Reaction
  作者：Yun-Bing Zhou、Yu-Qing Wang、Li-Chao Ning、Zong-Cang Ding、Wen-Long Wang、Cheng-Ke Ding、Ren-Hao Li、Jun-Jia Chen、Xin Lu、Yun-Jie Ding、Zhuang-Ping Zhan

  DOI：10.1021/jacs.7b00643

  日期：2017.3.22

  catalytic ligand for the PdII-catalyzed oxidative Heck reaction with high linear selectivity. The linear selectivity of CMP-1 is about 30 times higher than that of bipyridine-based monomer ligand. This work opens a new front of using CMP as an intriguing platform for developing highly efficient catalysts in controlling the regioselectivity in organic reactions.

  设计并合成了一系列含有 C≡C 键的吡啶型配体用于选择性氧化 Heck 反应。这些配体被用作功能单元并整合到共轭微孔聚合物的骨架中。6,6'-二碘-2,2'-联吡啶和1,3,5-三乙炔苯通过Sonogashira交叉偶联策略缩聚得到CMP-1材料。所得的 CMP-1 用作 PdII 催化的氧化 Heck 反应的多相催化配体，具有高线性选择性。CMP-1 的线性选择性比基于联吡啶的单体配体高约 30 倍。这项工作开辟了使用 CMP 作为开发高效催化剂控制有机反应区域选择性的有趣平台的新前沿。
• A conjugated microporous polymer as a recyclable heterogeneous ligand for highly efficient regioselective hydrosilylation of allenes
  作者：Ya-Nan Jiang、Jia-Hao Zeng、Ying Yang、Zhi-Kai Liu、Jun-Jia Chen、Ding-Chang Li、Li Chen、Zhuang-Ping Zhan

  DOI：10.1039/c9cc09387g

  日期：——

  The resultant Pd-CMP-1 was first applied as a highly efficient heterogeneous catalytic system for Pd-catalyzed allene hydrosilylation towards a wide range of allenes to produce branched allylsilanes with high regioselectivity. The ligand units of the polymer, along with the confinement effect of the porous structure, jointly regulated the regioselectivity. The parts-per-million (ppm) levels of Pd, coordinated

  含有相邻的C 3键，长度为m-C键的吡啶被用作配体单元，并被整合到共轭微孔聚合物的骨架中。首先将所得的Pd-CMP-1用作高效的多相催化体系，用于Pd催化的丙二烯向大范围的丙二烯进行氢化硅烷化，以生产具有高区域选择性的支链烯丙基硅烷。聚合物的配体单元以及多孔结构的限制作用共同调节了区域选择性。Pd的百万分之一（ppm）含量与可回收的异质配体配合使用，显示出工业应用前景。这项工作为使用CMP作为开发高效催化剂以控制丙二烯氢化硅烷化中的区域选择性的引人入胜的平台开辟了新的领域。
• Exo- and Endo-Receptors in One. A Novel Class of Supramolecular Structures Housing Transition-Metal-Binding Bi- and Terpyridine Units alongside Lithium Ion-Selective Trispirotetrahydrofuranyl Components
  作者：David G. Hilmey、Leo A. Paquette

  DOI：10.1021/jo030373t

  日期：2004.5.1

  The preparation of bipyridine and terpyridine ligands covalently linked via acetylenic and alkoxy tethers to rigid inositol orthoformate platforms is described. The constitution of compounds 3-6 is such that latent exo- and endo-receptor properties are simultaneously present with specific binding sites for Li+ and transition-metal ions. The 2-fold complexation in different regions is not dependent on prior molecular association. To gauge this unprecedented property, the model systems 11-14 were synthesized and their response to CuCl and FeCl2 probed by UV-vis and MS techniques. In a similar fashion, the ability of 3-6 to ligate lithium ions chemoselectively was evaluated by electrospray methods. The introduction of controlled amounts of both types of cation followed, and conversion to insoluble oligomeric products presumed to result from integral incorporation of the different metal ions in the expected fashion was achieved.