4-(2-pyridyl)pyrimidine | 52997-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(2-pyridyl)pyrimidine
• 英文别名: 2-(pyrimidin-4-yl)pyridine；4-(Pyridin-2-yl)pyrimidine；4-pyridin-2-ylpyrimidine
• CAS: 52997-82-7
• 化学式: C₉H₇N₃
• 分子量: 157.175
• InChiKey: LNNOIWAELUWVRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 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：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-(2-pyridyl)pyrimidine 在 正丁基锂 、 sodium hydride 作用下， 以 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 4,6-bis(2-pyridyl)pyrimidine
  参考文献：
  名称：

  Kraemer, R.; Fritsky, Igor O., European Journal of Organic Chemistry, 2000, # 20, p. 3505 - 3510

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙酰基吡啶 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 4-(2-pyridyl)pyrimidine
  参考文献：
  名称：

  通过自由基阴离子偶联合成一系列新型 6,6'-二取代 4,4'-双嘧啶：用于配位化学的新型 π 受体配体

  摘要：

  一个新的 6,6'-二取代 4,4'-联嘧啶配体家族已被制备和表征。通过循环伏安法测定的新配体的还原电位表明，这些新配体是比普遍存在的 2,2'-联吡啶配体更好的 π-受体，甚至优于未取代的母体 4,4'-联嘧啶配体。4,4'-联嘧啶的 6,6' 位置的取代基也会导致整个 UV 区域的 ππ* 和 nπ* 吸收发生红移。双嘧啶家族成员的 X 射线晶体结构表明，芳基取代基在固态时可以与嘧啶环共面。嘧啶环上的芳基取代基提供的额外电子离域作用有助于这些化合物更好的接受 π 能力。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  DOI：

  10.1002/ejoc.200500335

文献信息

• Mechanistic Studies on Ruthenium(II)-Catalyzed Base-Free Transfer Hydrogenation Triggered by Roll-Over Cyclometalation
  作者：Christian Kerner、Johannes Lang、Maximilian Gaffga、Fabian S. Menges、Yu Sun、Gereon Niedner-Schatteburg、Werner R. Thiel

  DOI：10.1002/cplu.201600526

  日期：2017.2

  The synthesis of 2-substituted pyridine-pyrimidine ligands and their complexation with arene ruthenium(II) chloride moieties is reported. Depending on the electronic and steric influences of the ligand, the catalysts undergo CH activation by roll-over cyclometalation. This process opens up the route to the catalytic transfer hydrogenation of ketones with isopropanol as the hydrogen source under base-free

  据报道2-取代的吡啶-嘧啶配体的合成及其与芳烃钌（II）氯化物的络合。取决于配体的电子和空间影响，催化剂通过翻转环金属化进行CH活化。该方法为在无碱温和条件下以异丙醇为氢源的酮催化转移加氢开辟了途径。可以通过碰撞诱导解离ESI质谱实验确定与翻转环金属化过程相关的障碍。它们得到DFT计算的支持，并允许根据配体的电子和空间特性对其进行分类，这也符合从X射线结构数据得出的关键键参数。
• PROCESS FOR PREPARING A PROPIOLIC ACID OR A DERIVATIVE THEREOF
  申请人：Goossen Lukas J

  公开号：US20140012000A1

  公开（公告）日：2014-01-09

  The invention relates to a process for preparing a propiolic acid or a derivative thereof by reacting a terminal alkyne with carbon dioxide, which comprises performing the reaction in the presence of a base and a copper complex, especially a copper (I) complex having at least one ligand, at least one of the ligands of the copper complex being selected from monodentate ligands which have an aminic or iminic nitrogen atom capable of coordination with copper, and polydentate ligands having at least two atoms or atom groups which are capable of simultaneous coordination with copper and are selected from nitrogen, oxygen, sulfur, phosphorus and carbene carbon.

  该发明涉及一种通过将末端炔烃与二氧化碳反应制备丙炔酸或其衍生物的方法，其中在碱和铜络合物的存在下进行反应，特别是在至少具有一个配体的铜（I）络合物的存在下进行反应，铜络合物的配体中至少有一个被选择自具有能够与铜配位的氨基或亚胺基氮原子的一价配体，以及具有至少两个能够与铜同时配位的原子或原子团的多齿配体，这些原子或原子团被选择自氮、氧、硫、磷和卡宾碳。
• Indolizines and pyrrolo[1,2-<i>c</i>]pyrimidines decorated with a pyrimidine and a pyridine unit respectively
  作者：Marcel Mirel Popa、Emilian Georgescu、Mino R Caira、Florentina Georgescu、Constantin Draghici、Raluca Stan、Calin Deleanu、Florea Dumitrascu

  DOI：10.3762/bjoc.11.121

  日期：——

  4-(2-pyridyl)pyrimidine the steric hindrance directs the reaction to the pyrimidinium N-ylides and, subsequently, to the formation of the pyrrolo[1,2-c]pyrimidines. The new pyrrolo[1,2-c]pyrimidines and the new indolizines were structurally characterized through NMR spectroscopy. The X-ray structures of two of the starting materials, 4-(2-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine, are also reported

  4-（吡啶基）嘧啶的三种可能的结构异构体通过其原位生成的相应N-酰基的1,3-偶极环加成反应，被用于合成新的吡咯并[1,2-c]嘧啶和新的吲哚嗪。它们相应的环溴化铵。在4-（3-吡啶基）嘧啶和4-（4-吡啶基）嘧啶的情况下，如预期在吡啶氮原子上发生季铵化反应，从而导致吡啶鎓溴化物，并因此经由相应的吡啶鎓N-烷基化物生成新的吲哚嗪。然而，在4-（2-吡啶基）嘧啶的情况下，位阻将反应引导至嘧啶N-酰基，然后引导至吡咯并[1,2-c]嘧啶的形成。通过NMR光谱对新的吡咯并[1,2-c]嘧啶和新的吲哚嗪进行结构表征。
• Molecular squares, rectangles and infinite helical chains utilising the simple ‘corner’ ligand 4-(2-pyridyl)-pyrimidine
  作者：Derek A. Beauchamp、Stephen J. Loeb

  DOI：10.1039/b206989j

  日期：——

  The ligand 4-(2-pyridyl)-pyrimidine forms multinuclear Ag(I) complexes by a combination of chelating and bridging coordination modes; molecular shape (square or rectangle) and degree of aggregation depend on the anion used.

  配体4-(2-吡啶基)-嘧啶通过螯合和桥联配位模式形成多核Ag(I)配合物；分子形状（正方形或矩形）和聚集程度取决于所用阴离子。
• Study of the coordination and solution structures for the interaction systems between diperoxidovanadate complexes and 4-(pyridin-2-yl)pyrimidine-like ligands
  作者：Xian-Yong Yu、Ping-Gui Yi、Dan-Hong Ji、Bi-Rong Zeng、Xiao-Fang Li、Xin Xu

  DOI：10.1039/c2dt12334g

  日期：——

  To understand the substitution effects of 4-(pyridin-2-yl)pyrimidine (pprd) on the coordination reaction equilibria, the interactions between a series of the pprd-like ligands and [OV(O2)2(H2O)]− or [OV(O2)2(HOD)]− or [OV(O2)2(D2O)]− (bpV) have been explored by a combination of multinuclear (1H, 13C, and 51V) magnetic resonance, heteronuclear single quantum coherence (HSQC) and variable temperature NMR in a 0.15 mol L−1 NaCl D2O solution that mimics physiological conditions. The direct NMR data are reported for the first time. Competitive coordination interactions result in a series of new hepta-coordinated peroxidovanadate species [OV(O2)2LL′]− (LL′ = pprd-like chelating ligands). The equilibrium constants for the products between bpV and the pprd-like ligands show that the relative affinity of the ligands is pprd ≈ 2-NH2-pprd > 2-Me-pprd > 2-Et-pprd > 4-(6-methylpyridin-2-yl)pyrimidine (abbr. 6′-Me-pprd). When the ligand is pprd, a pair of isomers (Isomer A and B) are observed in aqueous solution, which are attributed to the different types of coordination modes between the metal and the ligands, while the crystal structure of NH4[OV(O2)2(pprd)]·2H2O has the same coordination structure as Isomer A. For substituted pprd ligands, however, only one type of structure (Isomer A or B ) is observed in solution. These results demonstrate that, when the aromatic ring has a substitution group, both the steric effect (from the alkyl) and hydrogen bonding (from the amine) can affect the coordination reaction equilibrium to prevent the appearance of either Isomer B in solution for the ligands 2-Me-pprd, 2-NH2-pprd, 2-Et-pprd, or Isomer A in solution for 6′-Me-pprd.

  为了理解4-(吡啶-2-基)嘧啶(pprd)对配位反应平衡的取代效应,通过多核(^1H, ^13C, 和 ^51V)磁共振、异核单量子相干(HSQC)和变温核磁共振的组合,探索了一系列类似pprd的配体与[OV(O2)2(H2O)]−或[OV(O2)2(HOD)]−或[OV(O2)2(D2O)]−(bpV)在水溶液中的相互作用,水溶液模拟生理条件下的0.15 mol L−1 NaCl D2O溶液。首次报道了直接NMR数据。竞争性配位相互作用导致一系列新的七配位过氧化钒酸盐物种[OV(O2)2LL′]−(LL′=类似pprd的螯合配体)。bpV与类似pprd的配体之间产物的平衡常数表明,配体的相对亲和力为pprd≈2-NH2-pprd>2-Me-pprd>2-Et-pprd>4-(6-甲基吡啶-2-基)嘧啶(简称6′-Me-pprd)。当配体为pprd时,在水溶液中观察到一对异构体(异构体A和B),这归因于金属和配体之间不同的配位模式,而NH4[OV(O2)2(pprd)]·2H2O的晶体结构与异构体A具有相同的配位结构。然而,对于取代的pprd配体,在水溶液中只观察到一种结构(异构体A或B)。这些结果表明,当芳香环有取代基时,空间效应(来自烷基)和氢键(来自胺)都可以影响配位反应平衡,从而阻止异构体B在溶液中出现(对于配体2-Me-pprd, 2-NH2-pprd, 2-Et-pprd)或异构体A在溶液中出现(对于6′-Me-pprd)。