2-(6-bromopyridine-2-yl)-1,10-phenanthroline | 874379-37-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2-(6-bromopyridine-2-yl)-1,10-phenanthroline
• 英文别名: 2-(6-bromopyridin-2-yl)-1,10-phenanthroline；2-(6-bromopyrid-2-yl)-1,10-phenanthroline
• CAS: 874379-37-0
• 化学式: C₁₇H₁₀BrN₃
• 分子量: 336.19
• InChiKey: KNKHUVRCJJSKIM-UHFFFAOYSA-N

物化性质

• 熔点：
  >238 °C
• 沸点：
  515.9±45.0 °C(Predicted)
• 密度：
  1.536±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(6-bromopyridine-2-yl)-1,10-phenanthroline 在 bis(triphenylphosphine)palladium(II)-chloride copper(l) iodide 、 四丁基氟化铵 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 2-(6-ethynylpyrid-2-yl)-1,10-phenanthroline
  参考文献：
  名称：

  Synthetic Approaches to Polypyridyl Bridging Ligands with Proximal Multidentate Binding Sites

  摘要：

  A series of 12 bridging ligands was prepared. These ligands include a central linker appended to two 1,8-naphthyrid-2-yl or two 1,10-phenanthrolin-2-yl units. The linkers include pyridazin-3.6-diyl, 1,8-naphthyrid-2,7-diyl, 2,2'-bipyrid-6,6'-diyl, 1, 10-phenanthrolin-2,9-diyl, 1,2-di(2'-pyrid-6'-yl)ethyne, and 3,6-di(2'-pyrid-6'-yl)pyridazine. The ligands were synthesized from the diacetyl derivative of the central linker by a Friedlander condensation with either 2-aminonicotinaldehyde or 8-amino-7-quinolinecarbaldehyde. The precursor diacetyl derivatives were, in turn, prepared by pathways involving Stille and Sonogashira couplings. Examination of the electronic absorption spectra of the bridging ligands shows the strongest correlation to be between pairs of ligands having the same central linker. Complexation studies will follow.

  DOI：

  10.1021/jo051937r
• 作为产物：
  描述：

  2,6-二溴吡啶 在 四氢吡咯 、 正丁基锂 作用下， 以 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 120.0h， 生成 2-(6-bromopyridine-2-yl)-1,10-phenanthroline
  参考文献：
  名称：

  Synthetic Approaches to Polypyridyl Bridging Ligands with Proximal Multidentate Binding Sites

  摘要：

  A series of 12 bridging ligands was prepared. These ligands include a central linker appended to two 1,8-naphthyrid-2-yl or two 1,10-phenanthrolin-2-yl units. The linkers include pyridazin-3.6-diyl, 1,8-naphthyrid-2,7-diyl, 2,2'-bipyrid-6,6'-diyl, 1, 10-phenanthrolin-2,9-diyl, 1,2-di(2'-pyrid-6'-yl)ethyne, and 3,6-di(2'-pyrid-6'-yl)pyridazine. The ligands were synthesized from the diacetyl derivative of the central linker by a Friedlander condensation with either 2-aminonicotinaldehyde or 8-amino-7-quinolinecarbaldehyde. The precursor diacetyl derivatives were, in turn, prepared by pathways involving Stille and Sonogashira couplings. Examination of the electronic absorption spectra of the bridging ligands shows the strongest correlation to be between pairs of ligands having the same central linker. Complexation studies will follow.

  DOI：

  10.1021/jo051937r

文献信息

• A simple and efficient in situ generated ruthenium catalyst for chemoselective transfer hydrogenation of nitroarenes: kinetic and mechanistic studies and comparison with iridium systems
  作者：Bhaskar Paul、Kaushik Chakrabarti、Sujan Shee、Milan Maji、Anju Mishra、Sabuj Kundu

  DOI：10.1039/c6ra22221h

  日期：——

  Catalytic activities of a series of in situ generated homogeneous ruthenium systems based on commercially available [RuCl2(p-cymene)]2 and various ligands in transfer hydrogenation of nitroarenes to anilines were investigated. Combination...

  在将硝基芳烃加氢成苯胺的过程中，研究了基于市售[RuCl2（p-cymene）] 2和各种配体的一系列原位生成的均相钌体系的催化活性。组合...
• A solvent- and temperature-dependent intramolecular equilibrium of diamagnetic and paramagnetic states in Co complexes bearing triaryl amines
  作者：Linda Schnaubelt、Holm Petzold、Evgenia Dmitrieva、Marco Rosenkranz、Heinrich Lang

  DOI：10.1039/c8dt02538j

  日期：——

  dichloromethane. The Co3+/2+-centred redox event leads to a spin transition between the paramagnetic high-spin (HS) Co2+ and the diamagnetic low-spin (LS) Co3+ state, which was proven using 1H NMR and EPR spectroscopy. After one-electron oxidation of [Co(L)2](ClO4)2, an equilibrium between the diamagnetic [Co3+(L)]3+ and paramagnetic [Co2+(L)(L+)]3+ state in [Co(L)2]3+ (L = 1a–c) was found. Cyclic voltammetry

  络合物[CO（大号）2 ]（CLO 4）2（大号= Ö取代的2-（吡啶-2-基）-1,10-菲咯啉1A-1C含有三个氧化还原活性中心）（共2+离子和已合成了两个三芳基胺（Tara）单元。[Co（L）2 ]（ClO 4）2（L = 1a–c中的氧化步骤顺序使用循环伏安法和EPR / UV-vis-NIR光谱电化学法测定）。在乙腈溶液中，在室温下，首先进行氧化共中心化，然后在更高的阳极电势下进行塔拉氧化。在极性较小的溶剂二氯甲烷溶液中，氧化顺序相反。以Co 3 + / 2 +为中心的氧化还原事件导致顺磁性高自旋（HS）Co 2+与抗磁性低自旋（LS）Co 3+态之间发生自旋跃迁，这已通过1 H NMR和EPR光谱学。[Co（L）2 ]（ClO 4）2单电子氧化后，抗磁性[Co 3+（L）] 3+和顺磁性[Co 2+（L）（L +）] 3+处于[Co（L）2 ] 3+（L = 1a–c）状态。循环伏安法表明[Co
• Bis-meridional Fe²⁺ spincrossover complexes of phenyl and pyridyl substituted 2-(pyridin-2-yl)-1,10-phenanthrolines
  作者：Holm Petzold、Paul Djomgoue、Gerald Hörner、Charles Lochenie、Birgit Weber、Tobias Rüffer

  DOI：10.1039/c7dt02320k

  日期：——

  A series of Fe2+ SCO complexes of substituted 2-(pyridin-2-yl)-1,10-phenanthrolines 2 was prepared and the SCO (spincrossover) properties were characterized in the solid state (X-ray crystallography, SQUID magnetometry) and in solution (VT-1H NMR spectroscopy), augmented by theoretical modelling. Bis-meridional coordination of the tridendate 2a–c and tetradentate 2d ligands gives octahedral and distorted

  制备了一系列取代的2-（吡啶-2-基）-1,10-菲咯啉2的Fe 2+ SCO配合物，并在固态下表征了SC​​O（自旋交联）性质（X射线晶体学，SQUID磁力分析）在溶液中（VT- 1 H NMR光谱），通过理论建模得到增强。Tridendate 2a–c和四齿2d配体的双子午线配位分别给出了八面体和扭曲的三角十二面体复合物[Fe（2）2 ] 2+，它们被确定为转变温度为T 1/2的SCO复合物低于室温。SCO在固态被限制为溴-取代的[Fe（2A）2 ] 2+（道尔顿反式。，2017，46，6218-6229）和[Fe（上图2b）2 ] 2+与吡啶所附苯基，而溶液状态NMR研究揭示了所有配合物的SCO行为，这与DFT得出的结果一致。正如从其在HS状态下的N6（+2）配位所预期的，[Fe（2d）2 ] 2+的DFT结构建模识别出偏离结构保守的SCO反应坐标的偏差; 也就是说，Fe-N呼吸伴随
• Redox properties and electron transfer in a triarylamine-substituted HS-Co²⁺/LS-Co³⁺ redox couple
  作者：Linda Schnaubelt、Holm Petzold、J. Matthäus Speck、Evgenia Dmitrieva、Marco Rosenkranz、Marcus Korb

  DOI：10.1039/c6dt04748c

  日期：——

  complexes [Zn(1)2](ClO4)2 and [Co(2)2](BF4)2 allowing an assignment of changes in the electronic spectra to the redox states (2 = 2-(6-phenoxypyridin-2-yl)-1,10-phenanthroline). Although spectroelectrochemistry did not indicate substantial coupling between the redox centres the Tara unit is an efficient mediator for the self-exchange in the [Co2+/3+(1)2]2+/3+ couple. The electron transfer by self-exchange

  已开发出一种新的基于三齿菲咯啉-吡啶基的配体1，该配体1具有氧化还原活性Tara（三芳基胺）单元（1 = 4-（（6-（1,10-菲咯啉-2-基）吡啶-2-基]氧基）-N，N-二-对甲苯基苯胺）。制备了配合物[Co 2+（1）2 ]（ClO 4 / BF 4）2，并通过循环伏安法和EPR / UV-vis-NIR光谱电化学分析了氧化步骤的顺序。[Co 2+（1）2 ] 2+氧化为[Co 3+（1 +）2 ] 5+分两步进行。第一步是将Co 2 + / 3 +中心氧化为[Co 3+（1）2 ] 3+（E °'（M 2 + / 3 +）= 284 mV对Fc / Fc +），然后进行氧化Tara 0 / +中心的中心（E °'（Tara）= 531 mV）。在类似的配合物[Zn（1）2 ]（ClO 4）2和[Co（2）2 ]（BF 4）中独立研究了两种氧化过程。图2允许将电子光谱的变化分配给氧化还原态（
• Spin Transition and Charge Transfer in Co²⁺ /Co³⁺ Complexes of Meridional Ligands Holding Nearby Redox-active Triarylamine
  作者：Linda Schnaubelt、Holm Petzold、J. Matthäus Speck、Tobias Rüffer、Gerald Hörner、Heinrich Lang

  DOI：10.1002/zaac.201800274

  日期：2018.11.15

  Phenanthroline‐pyridyl bases containing a triarylamine (Tara) 1–4 and their respective Co2+ ([Co(L)2](ClO4)2, L = 1–4) and Co3+ complexes ([Co(L)2](ClO4)3–n(BF4)n, L = 2, 3) were prepared. The structure of [Co(3)2](ClO4)2 in the solid state was determined by single‐crystal X‐ray diffractometry. The oxidation processes of [Co(L)2](ClO4)2 (L = 1–4) were investigated by cyclic voltammetry. The first oxidation

  含三芳基胺（塔拉）菲咯啉吡啶基碱1 - 4以及它们各自的联合2+（[CO（大号）2 ]（CLO 4）2，大号= 1 - 4）和Co 3+络合物（[CO（大号）2 ]（CLO 4）3- ñ（BF 4）ñ，大号= 2，3）中制备。[Co（3）2 ]（ClO 4）2的结构通过单晶X射线衍射测定固态。的氧化过程[CO（大号）2 ]（CLO 4）2（大号= 1 - 4）通过循环伏安法研究。在第一氧化步骤[CO（大号）2 ]（CLO 4）2（大号= 1 - 3）在化学上是可逆的，并且钴为中心。此过程之后，塔拉单元在较高电势下发生不可逆氧化。在[Co（4）2 ]（ClO 4）2的情况下第一次氧化是以塔拉为中心的，并且是电化学可逆的。联合之间的电子耦合3+在原位离子和塔拉制备的Co（大号）2 ] 3+（大号= 2，3）通过UV /可见/近红外光谱电化学研究。在光谱的原位制备[CO（大号）2 ] 3+（大号=