3,3'-dimethyl-2,2'-bipyridine-N,N'-dioxide | 144900-66-3

• 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'-dimethyl-2,2'-bipyridine-N,N'-dioxide
• 英文别名: 5,5'-dimethyl-2,2'-bipyridine 1,1'-dioxide；5,5'-dimethyl-2,2'-bipyridine N,N'-dioxide；5,5'-dimethyl-2,2'-bipyridine-N,N'-dioxide；5,5'-dimethyl-2,2'-bipyridine di-N-oxide；5-Methyl-2-(5-methyl-1-oxopyridin-1-ium-2(1H)-ylidene)pyridin-1(2H)-olate；5-methyl-2-(5-methyl-1-oxidopyridin-2-ylidene)pyridin-1-ium 1-oxide
• CAS: 144900-66-3
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: HHVSSOZNWJKVJI-UHFFFAOYSA-N

物化性质

• 沸点：
  559.0±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3'-dimethyl-2,2'-bipyridine-N,N'-dioxide 在 硫酸二甲酯 作用下， 以 水 为溶剂， 生成 6,6'-dicyano-5,5'-dimethyl-2,2'-bipyridine
  参考文献：
  名称：

  Bipyridyls

  摘要：

  式I的化合物 ##STR1## 其中Y、Z、S、S'、m、n和R.sub.1-R.sub.4的定义如说明书所述，具有有价值的药物性质，特别是对原虫感染的有效性。它们是按照已知的方法制备的。

  公开号：

  US05354761A1
• 作为产物：
  描述：

  3-甲基吡啶氧化物 在 吡啶 、 palladium diacetate 、 silver carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以46%的产率得到3,3'-dimethyl-2,2'-bipyridine-N,N'-dioxide
  参考文献：
  名称：

  Pd-Catalyzed Oxidative CH/CH Direct Coupling of Heterocyclic N-Oxides

  摘要：

  A highly efficient protocol for C-H/C-H cross-coupling has been found to occur between 2-aryl-1,2,3-triazole N-oxides and pyridine N-oxide derivatives. In addition, two homocoupling reactions of 2-substituted 1,2,3-triazole N-oxides and some pyridine N-oxide derivatives were developed. A possible pathway of C-H/C-H direct coupling is discussed.

  DOI：

  10.1021/ol4019776

文献信息

• Synthesis and Spectroscopic Characterization of CN-Substituted Bipyridyl Complexes of Ru(II)
  作者：Catherine E. McCusker、James K. McCusker

  DOI：10.1021/ic102085b

  日期：2011.3.7

  steady state emission spectra of complexes 1−3 suggests all three compounds are characterized by excited-state geometries that are less distorted relative to their ground states as compared to [Ru(bpy)3](PF6)2; the effect of the more nested ground- and excited-state potentials is reflected in the unusually high radiative quantum yields (13% (1), 27% (2), and 40% (3)) and long 3MLCT-state room-temperature

  一系列钌配合物，其一般形式为[Ru（bpy）3 - n（CN-Me-bpy）n ]（PF 6）2（其中bpy = 2,2'-联吡啶，CN-Me-bpy = 4， 4'-二氰基-5,5'-二甲基-2,2'-联吡啶，和ñ = 1-3络合物1 - 3，分别地）被合成，并使用各种稳态和纳秒的特征在于时间分辨光谱学。电化学测量表明，CN-Me-bpy配体比未取代的联吡啶明显易于还原（约500 mV），这意味着最低的能量3MLCT（金属到配体的电荷转移）状态将与所有三种化合物中的CN-Me-bpy配体相关。复合物的稳态发射光谱从光谱拟合得到的黄-里斯因子的比较分析1 - 3表明所有三种化合物是由激发态的几何形状相对于它们的基态失真程度较小的相比的[Ru（联吡啶作为特征）3 ]（PF 6）2；更嵌套的基态和激发态电势的影响反映在异常高的辐射量子产率（13％（1），27％（2）和40％（3））和长3这些化合物的MLCT状态室温寿命（分别为1
• Preparation and Stereochemistry of Bis(1,10-phenanthroline)- and Bis(2,2′-bipyridine)chromium(III) Complexes Containing 2,2′-Bipyridine<i>N</i>,<i>N</i>′-Dioxide or Its 3,3′-Dimethyl Derivative
  作者：Hideaki Kanno、Kazuo Kashiwabara、Junnosuke Fujita

  DOI：10.1246/bcsj.53.2881

  日期：1980.10

  Bis(1,10-phenanthroline)- and bis(2,2′-bipyridine)chromium(III) complexes containing a seven-membered chelate ligand, 2,2′-bipyridine N,N′-dioxide(bpdo) or 3,3′-dimethyl-2,2′-bipyridine N,N′-dioxide(mbdo) were prepared. Each complex gave only one of two possible pairs of enantiomers resolved by SP-Sephadex column chromatography. On the basis of the circular dichroism spectra, molecular models, and

  双(1,10-菲咯啉)-和双(2,2'-联吡啶)铬(III)配合物含有七元螯合配体、2,2'-联吡啶N,N'-二氧化物(bpdo)或3，制备了 3'-二甲基-2,2'-联吡啶 N,N'-二氧化物 (mbdo)。通过 SP-Sephadex 柱色谱分离，每个复合物仅给出两对可能的对映异构体中的一个。基于圆二色性光谱、分子模型和从解析的 mbdo 复合物中回收光学活性游离 mbdo 配体，发现所有对映体对由 Δ(δ) 和 Λ(λ) 异构体组成，涉及偏斜ob 构型中的二氧化物螯合配体。
• Modular preparation of cationic bipyridines and azaarenes <i>via</i> C–H activation
  作者：Ryan P. King、Jenny Y. Yang

  DOI：10.1039/d3sc04864k

  日期：——

  preparation of trimethylammonium- and triarylphosphonium-substituted bipyridines and azaheterocycles is disclosed. This methodology showcases a C–H activation of pyridine N-oxides that enables a highly modular and scalable synthesis of a diverse array of cationically charged azaarenes. The addition of trimethylammonium functionalities on bipyridine derivatives resulted in more anodic reduction potentials (up

  联吡啶由于其氧化还原和光化学性质以及作为过渡金属配体的用途，在有机和无机化学中普遍存在。联吡啶和氮杂芳烃上的阳离子取代基作为强大的吸电子官能团很有价值，还可以提高在极性溶剂中的溶解度，但没有直接官能化的通用方法。公开了一种制备三甲基铵和三芳基鏻取代的联吡啶和氮杂杂环的通用方法。该方法展示了吡啶N-氧化物的 C-H 活化，能够高度模块化和可扩展地合成各种带阳离子电荷的氮杂芳烃。与中性未官能化联吡啶相比，在联吡啶衍生物上添加三甲基铵官能团可产生更高的阳极还原电位（高达 700 mV）并提高电化学可逆性。此外，4-三苯基膦化联喹啉金属化形成相应的 Re(CO) 3 Cl 络合物，导致还原电位比中性衍生物的阳极高 400 mV。
• Novel tetra- and hexa-dentate ligands from 6,6′-dicyano-2,2′-bipyridine
  作者：Paul N. W. Baxter、Joseph A. Connor、W. Bernd Schweizer、John D. Wallis

  DOI：10.1039/dt9920003015

  日期：——

  A simple, direct route from 2,2'-bipyridine to 6,6'-dicyano-2,2'-bipyridine and its conversion to the 6,6'-dithiocarboxamide and various novel tetra- and hexa-dentate ligands such as the 6,6'-bis(4-methyl-thiazol-2-yl) and 6,6'-bis[4-(2-pyridyl)thiazol-2-yl] derivatives have been established. Diaqua[6,6'-bis(4-methylthiazol-2-yl)-2,2'-bipyridine]zinc(II) bis(trifluoromethanesulfonate) has been prepared and its crystal structure determined. The tetra-heterocyclic ligand is planar, binding through two bipyridine nitrogen atoms and, more weakly, through two thiazolyl nitrogen atoms to zinc(ii) which is in a distorted octahedral environment.
• Pd-Catalyzed Oxidative CH/CH Direct Coupling of Heterocyclic <i>N</i>-Oxides
  作者：Wei Liu、Yahui Li、Yue Wang、Chunxiang Kuang

  DOI：10.1021/ol4019776

  日期：2013.9.20

  A highly efficient protocol for C-H/C-H cross-coupling has been found to occur between 2-aryl-1,2,3-triazole N-oxides and pyridine N-oxide derivatives. In addition, two homocoupling reactions of 2-substituted 1,2,3-triazole N-oxides and some pyridine N-oxide derivatives were developed. A possible pathway of C-H/C-H direct coupling is discussed.