(R)-(-)-2,2'-bipyridine-3,3'-dicarboxylic acid 1,1-dioxide | 169873-17-0

• 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: (R)-(-)-2,2'-bipyridine-3,3'-dicarboxylic acid 1,1-dioxide
• 英文别名: (+/-)-2,2'-bipyridine-3,3'-dicarboxylic acid 1,1-dioxide；(S)-(+)-2,2'-bipyridine-3,3'-dicarboxylic acid 1,1-dioxide；2,2'-bipyridine-3,3′-dicarboxylic acid 1,1'-dioxide；(R,S)-2,2'-bipyridyl-3,3'-dicarboxylic acid-1,1'-dioxide；(R,S)-2,2′-bipyridyl-3,3′-dicarboxylate-1,1′-dioxide；2,2'-bipyridyl-3,3'-dicarboxylic acid-1,1'-dioxide；H2bpdado；2,2'-Bipyridine-3,3'-dicarboxylic acid-1,1'-dioxide；2-(3-carboxy-1-oxopyridin-1-ium-2-ylidene)-1-oxidopyridine-3-carboxylic acid
• CAS: 169873-17-0
• 化学式: C₁₂H₈N₂O₆
• 分子量: 276.205
• InChiKey: UYACDOGCZTXMRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (R)-(-)-2,2'-bipyridine-3,3'-dicarboxylic acid 1,1-dioxide 以 甲醇 为溶剂， 生成 (R)-(+)-dimethyl 2,2'-bipyridine-3,3'-dicarboxylate 1,1-dioxide
  参考文献：
  名称：

  2,2'-联吡啶-3,3'-二羧酸1,1'-二氧化物及其酯的制备，拆分和绝对构型

  摘要：

  通过2,2'-联吡啶-3,3'-二羧酸的过氧化氢氧化制得的标题外消旋酸（±）-1通过水杨酸盐拆分。酸（+）- 1的绝对构型是使用Bijvoet异常分散法通过对其钡盐进行X射线衍射研究确定的。发现在50℃下用于二甲酯2的对映异构体的相互转化的活化能ΔG ＃为-106.5kJ / mol。

  DOI：

  10.1016/0957-4166(95)00160-q
• 作为产物：
  描述：

  2,2'-联吡啶-3,3'-二羧酸 在 双氧水 、 溶剂黄146 作用下， 反应 3.0h， 以92.8%的产率得到(R)-(-)-2,2'-bipyridine-3,3'-dicarboxylic acid 1,1-dioxide
  参考文献：
  名称：

  2,2'-联吡啶-3,3'-二羧酸1,1'-二氧化物及其酯的制备，拆分和绝对构型

  摘要：

  通过2,2'-联吡啶-3,3'-二羧酸的过氧化氢氧化制得的标题外消旋酸（±）-1通过水杨酸盐拆分。酸（+）- 1的绝对构型是使用Bijvoet异常分散法通过对其钡盐进行X射线衍射研究确定的。发现在50℃下用于二甲酯2的对映异构体的相互转化的活化能ΔG ＃为-106.5kJ / mol。

  DOI：

  10.1016/0957-4166(95)00160-q

文献信息

• {[Cu2(bpdado)2(H2O)2]·H2O}n: A 1D nanotubular coordination polymer with wall made of edge-sharing hexagons, where bpdado = 2,2′-bipyridine-3,3′-dicarboxylate-1,1′-dioxide
  作者：Fei Chang、Zhe-Ming Wang、Hao-Ling Sun、Song Gao、Ge-Hui Wen、Xi-Xiang Zhang

  DOI：10.1039/b509883a

  日期：——

  Utilizing 2,2′-bipyridine-3,3′-dicarboxylate-1,1′-dioxide and Cu2+ ions produces an antiferromagnetic, 1D nanotubular coordination polymer with its wall composed of edge-sharing hexagons, topologically similar to carbon nanotube.

  利用2,2-联吡啶-3,3-二羧酸-1,1-二氧化物和Cu2+离子生成反铁磁一维纳米管配位聚合物，其壁由共享边缘的六边形组成，拓扑结构类似于碳纳米管。
• High CO2 uptake capacity and selectivity in a N-oxide-functionalized 3D Ni(II) microporous metal–organic framework
  作者：Wen-Qian Zhang

  DOI：10.1016/j.poly.2020.114839

  日期：2021.1

  framework (MOF), [Ni(bpdado)(bpe)(H2O)2]·2DMF·2H2O}n (1), has been synthesized upon axially chiral N-Oxide-functionalized 2,2′-bipyridine-3,3′-dicarboxylate-1,1′-dioxide (H2bpdado) ligand with auxiliary rigid linear trans-1,2-bis (4-pyridyl)ethene (bpe) linker. Structural analysis reveals that there exist 1D diamond channels in the framework of 1, decorated with abundant N-Oxide “open donor sites”

  摘要合成了三维（3D）刚性Ni（II）微孔金属-有机骨架（MOF）[Ni（bpdado）（bpe）（H2O）2]·2DMF·2H2O} n（1）。轴向手性N-氧化物官能化的2,2'-联吡啶-3,3'-二羧酸-1,1'-二氧化物（H2bpdado）配体，带有辅助刚性线性反式1,2-双（4-吡啶基）乙烯（bpe ）链接器。结构分析表明，在1的框架中存在一维金刚石通道，并在孔表面饰有丰富的N氧化物“开放供体位点”（ODS）和空位羧基。吡啶-N修饰成N-氧化物基团使N-氧化物基团具有独特的电荷分离和富电子特性，这可以增强对CO2分子的亲和力。用N2，CH4和CO2研究了1'的气体吸附特性，
• Synthesis, structures and photoluminescence of a series of 3D lanthanide–organic coordination polymers constructed from versatile 2,2′-bipyridine-3,3′-dicarboxylic acid 1,1′-dioxide and oxalic acid
  作者：Lijuan Zhang、Hongwei Zhu、Yan Guo、Yunshan Zhou、Qing Yue、Zonghai Shi

  DOI：10.1039/c5ce00479a

  日期：——

  A series of 3D coordination polymers [Ln2(bdcd)(ox)2(H2O)3]·4H2O}n (Ln = Eu (1), Tb (2), Sm (3), Dy (4), and Gd (5)), which crystallize in the triclinic space group P with Z = 2, have been synthesized successfully based on the versatile ligands 2,2′-bipyridine-3,3′-dicarboxylic acid 1,1′-dioxide (H2bdcd) and oxalic acid (H2ox). The compounds were characterized by means of IR spectroscopy, elemental analysis, TG, and powder X-Ray diffraction, whereby compounds 1 and 2 were structurally characterized. All of the compounds are isomorphous and have a 3D open framework in which ox2− ligands bridge Ln3+ ions through their carboxylate groups resulting in the formation of a 1D Ln–ox infinite chain in the ac plane. The adjacent 1D Ln–ox infinite chains are then connected to each other through coordination interactions between Ln3+ ions and the carboxylate groups and N-oxide atoms of bdcd2− ligands resulting in a 3D (7,8)-connected open framework with a (38·49·54) (37·49·511·6) topology possessing 1D channels with lattice water molecules as residents. The photoluminescence properties of compounds 1, 2 and 4 were investigated in detail.

  一系列三维配位聚合物[Ln2(bdcd)(ox)2(H2O)3]Â-4H2O}n（Ln = Eu (1)、Tb (2)、Sm (3)、Dy (4) 和 Gd (5)）在三菱空间群 P 中结晶，Z = 2、的多功能配体 2,2â²-联吡啶-3,3â²-二羧酸 1,1â²-二氧化物（H2bdcd）和草酸（H2ox）成功合成。这些化合物通过红外光谱、元素分析、TG 和粉末 X 射线衍射进行了表征，其中化合物 1 和 2 的结构得到了表征。所有化合物都是同构的，具有三维开放框架，其中 ox2â 配体通过其羧酸基连接 Ln3+ 离子，从而在 ac 平面上形成一维 Lnâox 无限链。然后，相邻的一维 Lnâox 无限链通过 Ln3+ 离子与 bdcd2â 配体的羧酸基团和 N- 氧原子之间的配位相互作用相互连接，从而形成一个具有 (38Â-49Â-54) (37Â-49Â-511Â-6) 拓扑结构的三维 (7,8) 连接开放框架，该框架拥有以晶格水分子为居民的一维通道。对化合物 1、2 和 4 的光致发光特性进行了详细研究。
• Reaction-controlled assemblies and structural diversities of seven Co(<scp>ii</scp>)/Cu(<scp>ii</scp>) complexes based on a bipyridine-dicarboxylate N-oxide ligand
  作者：Quan-Quan Li、Yi-Fan Kang、Chun-Yan Ren、Guo-Ping Yang、Qing Liu, Ping Liu、Yao-Yu Wang

  DOI：10.1039/c4ce02008a

  日期：——

  Seven complexes, namely, [Co2[(R,S)-bpdado]2(CH3CN)2(H2O)2]·2H2O}n1, Cu[(R,S)-bpdado](H2O)}n2, [Cu2[(R,S)-bpdado]2(H2O)2]·H2O}n2′, [Cu(R,S)-bpdado]·EtOH}n2′′, Cu[(R,S)-bpdado](phen)}2 (phen = 1,10-phenanthroline) 3, Cu[(R,S)-bpdado](phen)(H2O)}2·8H2O 4 and Cu[(R,S)-bpdado](dpy)(H2O)}2·4H2O (dpy = 2,2′-pyridine) 5, have been obtained via solvothermal or layered diffusional reaction based on an axially chiral ligand, (R,S)-2,2′-bipyridyl-3,3′-dicarboxylic acid-1,1′-dioxide ((R,S)-H2bpdado). These complexes tend to form under thermodynamic control in the crystallization process of complexes. Among them, 2′ and 2′′ were reported and obtained along with the preparation of 2. Five new complexes, 1–5, are characterized by single-crystal X-ray diffraction, elemental analyses, X-ray powder diffraction, and IR and thermogravimetric analyses. Four different structural complexes, 2D achiral layers 1, 2 and 2′′ and 1D nanotubular structure 2′, are constructed by the M3[(R,S)-bpdado] tecton (M = Co(II) or Cu(II)) in different arrangement modes. When various N-donor ligands are used, different binuclear complexes, 3–5, are assembled by the Cu2[(R,S)-bpdado] tecton in the same arrangement mode. Apart from the arrangement modes of the tecton, some other elements are also discussed, which influence the final structures, such as the coordination modes and conformations of (R,S)-bpdado, the different metal ions, the reaction temperature, the N-donor ligand and the solvent system.

  七种配合物，即[Co2[(R,S)-双酚多酚]2(CH3CN)2(H2O)2]-2H2O}n1、Cu[(R,S)-双酚多酚](H2O)}n2、[Cu2[(R,S)-双酚多酚]2(H2O)2]-H2O}n2′、[Cu(R,S)-bpdado]-EtOH}n2′、Cu[(R,S)-bpdado](phen)}2（phen = 1,10-菲罗啉）3、Cu[(R,S)-bpdado](phen)(H2O)}2-8H2O 4 和 Cu[(R、S）-bpdado]（dpy）（H2O）}2-4H2O（dpy = 2,2′-吡啶）5、(R,S)-2,2′-联吡啶-3,3′-二甲酸-1,1′-二氧化物（(R,S)-H2bpdado）。这些络合物往往是在络合物结晶过程中受热力学控制形成的。通过单晶 X 射线衍射、元素分析、X 射线粉末衍射、红外分析和热重分析，对五种新络合物（1-5）进行了表征。通过 M3[(R,S)-bpdado] 构造（M = Co(II) 或 Cu(II)）以不同的排列模式构建了四种不同结构的配合物，即二维非手性层 1、2 和 2′′，以及一维纳米管结构 2′′。当使用不同的 N 供体配体时，Cu2[(R,S)-bpdado] 构造子以相同的排列模式组装出 3-5 种不同的双核配合物。除了构造子的排列模式外，还讨论了影响最终结构的一些其他因素，如 (R,S)-bpdado 的配位模式和构象、不同的金属离子、反应温度、N-主配体和溶剂系统。
• N-oxide-functionalized pillared Cd(II) porous metal−organic frameworks: Gas sorption and luminescent behavior
  作者：Wen-Qian Zhang、Wei Sun、Dong-Fei Wang、Wen-Rong Wu、Rui-Dong Wang、Lei-Lei Guo

  DOI：10.1016/j.jssc.2022.122993

  日期：2022.5

  Cd(II)-MOFs could provide effective “open donor sites” to enhance their affinity toward CO2 molecule. The gas adsorption properties of the Cd(II) framework have been investigated by N2, H2, CH4, and CO2 gases, and it reveals good CO2 uptake, CO2 sorption affinity, and sorption selectivity of CO2 over CH4 at ambient temperature. In addition, the solid-state luminescence properties of MOFs 1 and 2 have

  两种类似的 N-氧化物功能化柱状 Cd(II) 金属有机框架 (MOF)，[Cd(dpdcdo)(bpe) 0.5 (H 2 O)]·DMF·H 2 O} n ( 1 ) 和 [ Cd(dpdcdo)(bpe) 0.5 (H 2 O)]·DMA} n ( 2 ) [DMF = N,N-二甲基甲酰胺，DMA = N,N-二甲基乙酰胺]，已基于轴向手性获得2,2'-dipyridine-3,3'-dicarboxylate-1,1'-dioxide (H 2 dpdcdo) 配体和刚性反式-1,2-bis(4-pyridyl)ethene (bpe) 柱。Cd(II)-MOFs 通道中修饰的 N-Oxide 基团可以提供有效的“开放供体位点”以增强其对 CO 2的亲和力分子。Cd(II)骨架的气体吸附性能已经通过N 2、H 2、CH 4和CO 2气体进行了研究，显示出良好的CO 2吸收、CO