2,2-联吡啶-5-羧酸 | 1970-80-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 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
• 中文名称: 2,2-联吡啶-5-羧酸
• 中文别名: 2,2'-联吡啶-5-羧酸
• 英文名称: 2,2'-bipyridine-5-carboxylic acid
• 英文别名: 5-carboxy-2,2'-bipyridine；(2,2’-bipyridine)-5-carboxylic acid；2,2'-bipyridyl-5-carboxylic acid；2,2’-bipyridinyl-5-carboxylic acid；[2,2'-Bipyridine]-5-carboxylic acid；6-pyridin-2-ylpyridine-3-carboxylic acid
• CAS: 1970-80-5
• 化学式: C₁₁H₈N₂O₂
• 分子量: 200.197
• InChiKey: LWMHPOLRJIRLPN-UHFFFAOYSA-N

物化性质

• 熔点：
  218-220 °C
• 沸点：
  405.5±35.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 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：
  63.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090
• 储存条件：
  室温且干燥环境下使用。

反应信息

• 作为反应物：
  描述：

  2,2-联吡啶-5-羧酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 methyl 2,2'-bipyridine-5-carboxylate
  参考文献：
  名称：

  含不对称配体的钌（II）的tris-2,2'-联吡啶配合物的分离和纯化

  摘要：

  含不对称单体钌（II）配合物[Ru（L）3 ] 2+联吡啶 配体 [其中L = 5-甲基-2,2'-联吡啶（L 1），5-乙基-2,2'-联吡啶（L 2），5-丙基-2,2'-联吡啶（L 3），5-（2-甲基丙基）-2,2'-联吡啶（L 4），5-（2,2-二甲基丙基）-2,2'-联吡啶（L 5）或5-（甲氧甲氧基）-2,2'-联吡啶（L 6）]已被研究，通过使用阳离子交换柱 色谱法 （SP Sephadex C-25）用以下任何一种洗脱 甲苯-4-磺酸钠 或者 己酸钠。发现面部异构体的相对产率随着空间体积的增加而降低，从而阻止了fac- [Ru（L 5）3 ] 2+的分离。两种异构形式的特征在于1 H NMR光谱，其配合物[Ru（L 1–3）3 ] 2+表现出H 6和H 4之间异常大的偶联 质子。以子午和面异构体的混合物形式获得了适合[Ru（L 1）3 ] 2+的X射线结构分析的晶体，表

  DOI：

  10.1039/b104365j
• 作为产物：
  描述：

  2-(三甲基甲锡烷基)吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 23.0h， 生成 2,2-联吡啶-5-羧酸
  参考文献：
  名称：

  A convergent approach to protein design. Metal ion-assisted spontaneous self-assembly of a polypeptide into a triple-helix bundle protein

  摘要：

  A novel metal ion-assisted self-organizing molecular process is described by which a small peptide has been assembled into a large and topologically predetermined protein tertiary structure. The intrinsic binding energy of a metal ion coordination complex as well as the stringent geometrical requirements present for a strong metal ion-ligand interaction has been exploited to control the oligomeric state as well as the relative orientation of peptide subunits participating in an intermolecular assembly process. A 15-residue amphiphilic peptide with a 2,2'-bipyridine functionality at the N-terminus was designed and shown to undergo spontaneous self-assembly, in the presence of transition metal ions, to form a 45-residue triple-helical coiled-coil metalloprotein.

  DOI：

  10.1021/ja00029a004

文献信息

• pH-Dependent ion permeability control of a modified amphotericin B channel through metal complexation
  作者：Tomomi Koshiyama、Yuki Inoue、Sana Asada、Koki Kawahara、Shogo Ide、Kazuma Yasuhara、Masaaki Ohba

  DOI：10.1039/d0cc08368b

  日期：——

  Amphotericin B incorporated with a metal-binding site within a membrane exhibited pH-dependent ion permeability with a response to Cu²⁺ ions selectively.

  阿莫西林B与膜内的金属结合位点结合，在膜中表现出依赖于pH的离子渗透性，对Cu²⁺离子具有选择性响应。
• Self-stacking of naphthalene bis(dicarboximide)s probed by NMR †
  作者：Vera Steullet、Dabney W. Dixon

  DOI：10.1039/a801441h

  日期：——

  The self-stacking in water of a series of naphthalene-1,8∶4,5-bis(dicarboximide)s (also known as naphthalene diimides, NDIs) bearing cationic side chains has been studied using NMR techniques. The position of the charge in the side chain has a strong effect on the propensity of the NDI to self-stack. Examples with a cationic center three atoms away from the NDI ring in general do not self-stack; those with cationic centers further out on the side chains are prone to self-stack at NMR concentrations. The size of the side chain per se does not appear to be a significant controlling factor; even a derivative with biotin side chains shows no evidence of self-stacking. Increasing the ionic strength of the solution can also induce stacking. Derivatives with aromatic side chains can show intramolecular self-stacking of the side chain with the central NDI ring. This is significant for side chains with isoquinoline and bipyridine groups but not significant for side chains with pyridine groups. An example of an NDI that undergoes both intramolecular and intermolecular stacking is the derivative bearing side chains ending in Ru(bpy)32+ moieties. In methanol, the shift patterns of the aromatic resonances of the bipyridine rings are very close to those of a model compound. However, a more complicated chemical shift pattern is seen in water. This indicates that conformations with the Ru(bpy)32+ moieties lying at least partly within the shielding cone of the aromatic NDI system are favored. Molecular modeling indicates that conformations in which the bipyridine ring interacts with the NDI ring are readily achievable. The temperature dependence of the chemical shifts for this molecule indicates that both intramolecular interactions of the bipyridine rings with the NDI ring and self-stacking of the NDI rings are significant.

  使用核磁共振技术研究了一系列带有阳离子侧链的萘-1,8‖4,5-双(二氧亚胺)(也称为萘二亚胺,NDI)在水中的自堆叠现象。侧链上的电荷位置对NDI的自堆叠倾向有强烈影响。通常,阳离子中心与NDI环相隔三原子的例子不会自堆叠;而阳离子中心位于侧链更远处的则倾向于在核磁共振浓度下自堆叠。侧链的大小本身似乎不是重要的控制因素;甚至带有生物素侧链的衍生物也未显示出自堆叠的证据。增加溶液的离子强度也可以诱导堆叠。带有芳香侧链的衍生物可以显示侧链与中央NDI环的分子内自堆叠。这对于带有异喹啉和联吡啶基团的侧链是显著的,但对于带有吡啶基团的侧链则不显著。一个同时经历分子内和分子间堆叠的NDI例子是带有侧链末端为Ru(bpy)32+基团的衍生物。在甲醇中,联吡啶环的芳香共振位移模式与模型化合物非常接近。然而,在水中的化学位移模式更为复杂。这表明,Ru(bpy)32+基团至少部分位于芳香NDI系统的屏蔽锥内的构象是受青睐的。分子模拟表明,联吡啶环与NDI环相互作用的构象容易实现。该分子化学位移的温度依赖性表明,联吡啶环与NDI环的分子内相互作用以及NDI环的自堆叠都是显著的。
• Hydrogen Bond Directed <i>ortho</i> ‐Selective C−H Borylation of Secondary Aromatic Amides
  作者：Shao‐Tao Bai、Charles B. Bheeter、Joost N. H. Reek

  DOI：10.1002/anie.201907366

  日期：2019.9.9

  iridium catalyst for ortho‐selective C−H borylation of challenging secondary aromatic amide substrates, and the regioselectivity is controlled by hydrogen‐bond interactions. The BAIPy‐Ir catalyst forms three hydrogen bonds with the substrate during the crucial activation step, and allows ortho‐C−H borylation with high selectivity. The catalyst displays unprecedented ortho selectivities for a wide variety

  据报道是一种铱催化剂，可用于具有挑战性的二级芳族酰胺底物的邻位选择性CH硼化，其区域选择性受氢键相互作用的控制。所述BAIPy -Ir催化剂在至关重要的激活步骤形成与所述衬底三个氢键，并且允许邻-C-H硼化高选择性。该催化剂 对电子和空间特性不同的多种底物显示出空前的邻位选择性，并且该催化剂可耐受各种官能团。区域选择性CH硼化催化剂易于获得，并以高选择性和高转化率以克为单位转化底物。
• Bioinspired aerobic oxidation of alcohols with a bifunctional ligand based on bipyridine and TEMPO
  作者：Lianyue Wang、Zhixing Bie、Sensen Shang、Ying Lv、Guosong Li、Jingyang Niu、Shuang Gao

  DOI：10.1039/c6ra05536b

  日期：——

  A novel bioinspired bifunctional ligand incorporating metal-binding site and stable free radical has been synthesized. The catalytic system obtained from the bifunctional ligand with copper(I) iodide in the presence of...

  合成了一种新型的生物启发的双功能配体，该配体结合了金属结合位点和稳定的自由基。在...的存在下由双功能配体与碘化铜（I）制得的催化体系
• Intramolecular CH Bond Activation through a Flexible Ester Linkage
  作者：Christopher J. Shaffer、Detlef Schröder、Christoph Gütz、Arne Lützen

  DOI：10.1002/anie.201203163

  日期：2012.8.6

  Replacing the director: A bipyridinyl ligand with an aliphatic side chain determines the regioselectivity of copper‐catalyzed CH oxidation by intramolecular effects. Because the aliphatic chain is attached through an ester linkage, the catalytic cycle can in principle be closed by transesterification. Ion‐mobility mass spectrometry and isotopic labeling provide mechanistic insight not available from

  更换导演：与脂肪族侧链的联吡啶配体的确定铜催化C中的区域选择性 ħ氧化通过分子内的效果。因为脂族链通过酯键连接，原则催化循环可以通过酯交换反应被关闭。的离子迁移质谱仪和同位素标记提供不提供直接的质谱实验机械性的认识。