3,3',5,5'-tetrabromo-4,4'-bipyridine | 1227402-68-7

• 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: 3,3',5,5'-tetrabromo-4,4'-bipyridine
• 英文别名: 2,2',4,4'-tetrabromobipyridine；3,5,3',5'-tetrabromo-[4,4']bipyridinyl；3,5-dibromo-4-(3,5-dibromopyridin-4-yl)pyridine
• CAS: 1227402-68-7
• 化学式: C₁₀H₄Br₄N₂
• 分子量: 471.771
• InChiKey: MCZBHSJOYUQKDS-UHFFFAOYSA-N

物化性质

• 熔点：
  148-150 °C
• 沸点：
  363.2±37.0 °C(Predicted)
• 密度：
  2.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• 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：

  3,3',5,5'-tetrabromo-4,4'-bipyridine 、 Phosphine, phenylbis(trimethylstannyl)- 在 1,1'-偶氮(氰基环己烷) 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 反应 48.0h， 以16%的产率得到trans-4,8-diphenylphosphindolo[4,3,2-bcd]bipyridine 2,8-sulfide
  参考文献：
  名称：

  应变双桥双联芳烃和紫精的合成及物理性质

  摘要：

  新的含P / N的包含全平面联芳基阵列的π电子系统是通过多自由基磷酰化反应合成的。在这些高度应变的平面π系统中的联芳基部分通过双P桥接而被硬化。核心联芳基实体的电子性质可通过引入N供体取代基或在π系统内安装N原子来改变，从而转变为紫精核心结构。对这些化合物的电化学和光物理性质进行了讨论，并与相关系统进行了比较。

  DOI：

  10.1002/chem.201605272
• 作为产物：
  描述：

  3,5-二溴吡啶 在 lithium diisopropyl amide 、 氧气 、 copper dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 以71%的产率得到3,3',5,5'-tetrabromo-4,4'-bipyridine
  参考文献：
  名称：

  应变双桥双联芳烃和紫精的合成及物理性质

  摘要：

  新的含P / N的包含全平面联芳基阵列的π电子系统是通过多自由基磷酰化反应合成的。在这些高度应变的平面π系统中的联芳基部分通过双P桥接而被硬化。核心联芳基实体的电子性质可通过引入N供体取代基或在π系统内安装N原子来改变，从而转变为紫精核心结构。对这些化合物的电化学和光物理性质进行了讨论，并与相关系统进行了比较。

  DOI：

  10.1002/chem.201605272

文献信息

• Synthesis, Resolution, and Absolute Configuration of Chiral 4,4′-Bipyridines
  作者：Victor Mamane、Emmanuel Aubert、Paola Peluso、Sergio Cossu

  DOI：10.1021/jo300286z

  日期：2012.3.16

  A chiral polyhalogenated 4,4′-bipyridine derivative is described allowing an easy access to a new family of chiral 4,4′-bipyridines by site-selective cross-coupling reactions. The absolute configurations of all the HPLC separated enantiomers were determined by X-ray diffraction and electronic circular dichroism coupled with time-dependent density functional theory calculations.

  描述了手性多卤代的4,4'-联吡啶衍生物，其允许通过位点选择性交叉偶联反应容易地获得新的手性4,4'-联吡啶家族。通过X射线衍射和电子圆二色性以及与时间相关的密度泛函理论计算，确定了所有HPLC分离的对映异构体的绝对构型。
• Silver(<scp>i</scp>) coordination polymers with 3,3′,5,5′-tetrasubstituted 4,4′-bipyridine ligands: towards new porous chiral materials
  作者：E. Aubert、M. Abboud、A. Doudouh、P. Durand、P. Peluso、A. Ligresti、B. Vigolo、S. Cossu、P. Pale、V. Mamane

  DOI：10.1039/c6ra28197d

  日期：——

  Coordination polymers (CP) assembled from 3,3′,5,5′-tetrasubstituted 4,4′-bipyridines and silver salts have been prepared and characterized by X-ray diffraction. Silver-CPs based on infinite Ag–bipyridine chains were obtained where one or two halogen atoms strongly interacted with Ag. A homochiral MOF was also prepared using the enantiopure 3,3′-dibromo-5,5′-bis(4-methoxyphenyl)-4,4′-bipyridine as

  已经制备了由3,3'，5,5'-四取代的4,4'-联吡啶和银盐组装而成的配位聚合物（CP），并通过X射线衍射对其进行了表征。获得了基于无限个Ag-联吡啶链的银CPs，其中一个或两个卤素原子与Ag强烈相互作用。还使用对映纯3,3'-二溴-5,5'-双（4-甲氧基苯基）-4,4'-联吡啶作为配体制备了同手性MOF，而其外消旋形式仅形成了紧凑的CP。初步的应用表明，同手性网络能够识别外消旋-环氧乙烷的对映异构体，并能控制基于Ag的MOF对源自成年人类皮肤（HaCaT）的细胞系的细胞毒性水平。
• Synthesis of Polyhalogenated 4,4′-Bipyridines via a Simple Dimerization Procedure
  作者：Mohamed Abboud、Victor Mamane、Emmanuel Aubert、Claude Lecomte、Yves Fort

  DOI：10.1021/jo100152e

  日期：2010.5.21

  Polyhalogenated 4,4'-bipyridines were conveniently synthesized in a single step starting from dihalo-pyridines. A mechanism was proposed on the basis of experiments performed with 2-chloro-5-bromopyridine I a. 2-Chloro-4-lithio-5-bromopyridine A1 was produced via ortholithiation of la by using either LDA or t-BuLi bases. When LDA was used, chiller 3a containing two chlorines and two bromine atoms was formed predominantly accompanied by several byproducts whose structure and mechanism of formation are discussed. In the case of t-BuLi, although the major product was 2-chloropyridine 7, a new pyridone product 8 was formed that is probably the result of the dihydropyridine intermediate hydrolysis. The dimerization procedure involving LDA was employed to prepare a large number of halogenated 4,4'-bipyridines in moderate to good yields. In some specific cases, halogenated 3,4' and 2,4'-bipyridines were obtained in lower yields and their structures were unambiguously assigned by X-ray diffraction analysis.
• Synthesis and Physical Properties of Strained Doubly Phosphorus-Bridged Biaryls and Viologens
  作者：Tobias W. Greulich、Eriko Yamaguchi、Carsten Doerenkamp、Maximilian Lübbesmeyer、Constantin G. Daniliuc、Aiko Fukazawa、Hellmut Eckert、Shigehiro Yamaguchi、Armido Studer

  DOI：10.1002/chem.201605272

  日期：2017.5.2

  moiety in these highly strained planar π‐systems is rigidified by double P‐bridging. The electronic properties of the core biaryl entity are varied by introducing N‐donor substituents or by installing N‐atoms within the π‐system, thereby moving to the viologen core structure. The electrochemical and photophysical properties of these compounds are discussed and compared with those of related systems

  新的含P / N的包含全平面联芳基阵列的π电子系统是通过多自由基磷酰化反应合成的。在这些高度应变的平面π系统中的联芳基部分通过双P桥接而被硬化。核心联芳基实体的电子性质可通过引入N供体取代基或在π系统内安装N原子来改变，从而转变为紫精核心结构。对这些化合物的电化学和光物理性质进行了讨论，并与相关系统进行了比较。