N₁,N₂-bis(pyridin-4-ylmethylene)ethane-1,2-diamine | 3189-97-7

• 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: N₁,N₂-bis(pyridin-4-ylmethylene)ethane-1,2-diamine
• 英文别名: N,N'-Bis-(pyridin-4-al)-ethylen-diimin；N,N'-(1,2-ethanediyl)bis(1-(4-pyridyl)methanimine)；1-pyridin-4-yl-N-[2-(pyridin-4-ylmethylideneamino)ethyl]methanimine
• CAS: 3189-97-7
• 化学式: C₁₄H₁₄N₄
• 分子量: 238.292
• InChiKey: OGWUZLCBMXNPMT-UHFFFAOYSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  415.2±30.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N₁,N₂-bis(pyridin-4-ylmethylene)ethane-1,2-diamine 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 4.0h， 以29%的产率得到N,N′‐bis(pyridin‐4‐ylmethyl)ethane‐1,2‐diamine
  参考文献：
  名称：

  Synthesis and biological evaluation of novel cYY analogues targeting Mycobacterium tuberculosis CYP121A1

  摘要：

  The rise in multidrug resistant (MDR) cases of tuberculosis (TB) has led to the need for the development of TB drugs with different mechanisms of action. The genome sequence of Mycobacterium tuberculosis (Mtb) revealed twenty different genes coding for cytochrome P450s. CYP121A1 catalyzes a C-C crosslinking reaction of di-cyclotyrosine (cYY) producing mycocyclosin and current research suggests that either mycocyclosin is essential or the overproduction of cYY is toxic to Mtb. A series of 1,4-dibenzyl-2-imidazol-1-yl-methylpiperazine derivatives were designed and synthesised as cYY mimics. The derivatives substituted in the 4-position of the phenyl rings with halides or alkyl group showed promising antimycobacterial activity (MIC 6.25 mu g/mL), with the more lipophilic branched alkyl derivatives displaying optimal binding affinity with CYP121A1 (Pr-i K-D = 1.6 mu M; Bu-t K-D = 1.2 mu M). Computational studies revealed two possible binding modes within the CYP121A1 active site both of which would effectively block cYY from binding.

  DOI：

  10.1016/j.bmc.2019.02.051
• 作为产物：
  描述：

  4-吡啶甲醛 、 乙二胺 以 乙醇 为溶剂， 反应 3.0h， 以80%的产率得到N₁,N₂-bis(pyridin-4-ylmethylene)ethane-1,2-diamine
  参考文献：
  名称：

  通过C═C偶联进行温度依赖性的原位配体环化和自旋交叉铁（II）配位聚合物的形成

  摘要：

  的反应Ñ 1，Ñ 2 -二（吡啶-4-基亚甲基）乙烷-1,2-二胺（大号）以Fe（NCS）2的各种温度下产生了3个铁（II）的配位聚合物，即，一个维[Fe（L'）（NCS）2 ]（1），二维[Fe（L）2（NCS）2 ]·H 2 O（2）和一维[Fe（L）2（ NCS）2 ]·2CH 2 Cl 2 ·4MeOH（3）。1的形成涉及一个原位C═C偶联反应，L与L' [ L' = 5,6-二（吡啶-4-基）-1,2,3,4-四氢吡嗪]，该反应被分解为氰化物的离子催化硫氰酸盐 还合成了1的锰（II）（1a）和锌（II）（1b）类似物进行比较。磁性研究表明，配合物1经历了压力依赖性的一步不完全自旋转变，而配合物2和3在整个温度范围内都是顺磁性的。

  DOI：

  10.1021/ic101490a

文献信息

• Design, Synthesis, and Characterizations of a Series of Pt₄ Macrocycles and Fluorescent Sensing of Fe³⁺/Cu²⁺/Ni²⁺ Through Metal Coordination
  作者：Sushobhan Ghosh、Rajesh Chakrabarty、Partha Sarathi Mukherjee

  DOI：10.1021/ic801381p

  日期：2009.1.19

  of hard transition metal ions (Fe3+, Cu2+, Ni2+, and Mn2+) into the N4 pocket. The nonresponsive nature of the fluorescence intensity upon the addition of soft metal ions (Zn2+ and Cd2+) having d10 configuration makes it a suitable sensor for transition metal ions. The fluorescence intensity of the Ni2+ bound complex was regained when the metal was removed by a stronger chelating 2,2′-dipyridyl ligand

  合成了含有乙炔基官能团的Pt II 2有机金属“夹子”（1a）。多核NMR和电喷雾电离质谱法表征了这种“夹子”，并且在X射线单晶衍射研究中确定了分子结构。一系列离散的分子矩形（的2A - d）已经从这个“夹子”合成结合吡啶基于线性接头（大号1-4）通过金属-配位体配位驱动的自组装方法[其中大号1 = 4 ，4'-联吡啶，L 2＝反式-1,2-双（4-吡啶基）乙烯，L 3＝ N-（4-吡啶基）异烟酰胺，L 4＝ N，N′-双（4-吡啶基）乙二胺]。使用基于亚胺的配体L 4设计矩形2d，使其成为由荧光团-受体-荧光团组合组成的系统。亚胺N 4口袋是受体位点，而蒽基“片段”是荧光团。配合物2d本质上是荧光的，当硬过渡金属离子（Fe 3+，Cu 2 +，Ni 2+和Mn 2+）结合到N 4中时，溶液中的荧光猝灭口袋。在添加具有d 10构型的软金属离子（Zn 2+和Cd 2+）时，荧光强度的无响应特
• Supramolecular assembly of metalloporphyrins in crystals by axial coordination through amine ligands
  作者：Yael Diskin-Posner、Goutam Kumar Patra、Israel Goldberg

  DOI：10.1039/b104961p

  日期：——

  Axial coordination to metalloporphyrins is an important tool in the supramolecular chemistry of these entities. Metalated 5,10,15,20-tetraphenylporphyrins can be axially linked to each other with the aid of amine and diamine ligands. Seven new crystalline materials consisting of such heterogeneous coordination oligomers and polymers of Zn(II)– or Mn(III)–tetraphenylporphyrins have been prepared and

  轴向协调 金属卟啉是这些实体的超分子化学中的重要工具。金属化的5,10,15,20-四苯基卟啉可以借助胺 和 二胺 配体。由这种异质配位低聚物和聚合物制备了Zn（II）–或Mn（III）–四苯基卟啉，并进行了表征X射线晶体学。 配体 长度不同的已被用作桥架金属中心之间的桥接助剂。 卟啉 种，影响异质性 卟啉--配体低聚物以及聚合物组件。这些分别对应于超分子支架的“轮轴”和“烤肉串”型形状。此外，独特的结构同质协调聚合物Zn（II）-四吡啶基卟啉衍生物的合成也有报道。
• Copper(II) Schiff base complex immobilized on graphene nanosheets: a heterogeneous catalyst for epoxidation of olefins
  作者：Ali Zarnegaryan、Zari Pahlevanneshan、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani、Iraj Mohammdpoor-Baltork

  DOI：10.1007/s13738-018-1552-3

  日期：2019.4

  inductively coupled plasma atomic emission spectroscopy. The catalytic activity of the heterogeneous catalyst was studied in the epoxidation of various alkenes using tert-butyl hydroperoxide as an oxidant and it showed high selectivity and catalytic reactivity. The graphene-bound copper Schiff base was successfully reused for several runs without significant loss in its catalytic activity.

  本文描述了固定在氧化石墨烯上的Cu（II）Schiff碱配合物的制备和表征。非均相催化剂的结构和形态表征是通过不同的技术进行的，例如傅立叶变换红外光谱和漫反射紫外可见光谱，X射线衍射，热重分析，氮吸附-解吸，透射电子显微镜，场发射扫描电子显微镜和电感耦合等离子体原子发射光谱。多相催化剂的催化活性使用各种烯烃的环氧化进行了研究叔丁基过氧化氢作为氧化剂，它具有很高的选择性和催化反应活性。石墨烯结合的席夫铜碱已成功地重复使用了几次，而其催化活性没有明显损失。
• Size and function influence study on enhanced catalytic performance of a cooperative MOF for mild, green and fast C–C bond formation
  作者：Najmeh Varnaseri、Farzaneh Rouhani、Ali Ramazani、Ali Morsali

  DOI：10.1039/d0dt00433b

  日期：——

  Tuning of pore function and size (surface area) are two key factors that play important roles in the performance of metal–organic-frameworks (MOFs) as catalysts.

  孔功能和大小（表面积）的调节是金属-有机框架（MOFs）作为催化剂性能中起重要作用的两个关键因素。
• Building-up novel coordination polymer with Zn(II) porphyrin dimer: Synthesis, structures, surface morphology and effect of axial ligands
  作者：S K ASIF IKBAL、SANFAORI BRAHMA、AVINASH DHAMIJA、SANKAR PRASAD RATH

  DOI：10.1007/s12039-014-0686-9

  日期：2014.9

  Highly flexible Zn(II)1,2-bis(meso-octaethylporphyrin)ethane (1) has been used as host in which two porphyrin rings are found to be face-to-face in non-coordinating solvents. Upon addition of one relatively smaller 4,4′-dipyridine (L1) and one extended N,N′-bispyridine-4-yl-methylene ethylenediamine (L2) guest ligands, the syn conformation of 1 is switched to the anti complexes 1∙(L1)2 and 1∙L 2, respectively. Single crystal X-ray structures of all the complexes are reported in which a stable one-dimensional coordination polymer is produced only in 1∙L 2 that is, to the best of our knowledge, the first structural report of 1D-coordination polymer with porphyrin dimer. Solution structures of the complexes along with binding studies in solution between 1 and L have also been investigated. The morphology of the polymeric complex 1∙L 2 on silicon wafer surface was examined by Atomic Force Microscopy (AFM) in which the crystalline islands of well defined facets of size ranging from 200–550 nm perimeter and a height of 20–40 nm have been observed.

  高柔性锌（II）1,2-双（中辛基乙基卟啉）乙烷（1）已被用作宿主，其中两个卟啉环在非配位溶剂中面对面。在加入一个相对较小的 4,4′-二吡啶（L1）和一个扩展的 N,N′-二吡啶-4-基亚甲基乙二胺（L2）客体配体后，1 的合成构象分别转换为反配合物 1∙(L1)2 和 1∙L 2。报告了所有配合物的单晶 X 射线结构，其中只有 1∙L 2 产生了稳定的一维配位聚合物，据我们所知，这是第一份关于卟啉二聚体一维配位聚合物的结构报告。我们还研究了复合物的溶液结构以及 1 和 L 之间的溶液结合研究。原子力显微镜（AFM）对硅晶片表面的聚合物复合物 1∙L 2 的形态进行了研究，观察到周长为 200-550 纳米、高度为 20-40 纳米、具有明确刻面的结晶岛。