2,6-二-(1-咪唑)吡啶 | 39242-17-6

• 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: 2,6-二-(1-咪唑)吡啶
• 英文名称: 2,6-bis(1-imidazolyl)pyridine
• 英文别名: 2,6-bis(imidazol-1-yl)pyridine；2,6-di(1H-imidazol-1-yl)pyridine；2,6-bis(1-imdazoly)pyridine；2,6-bis(imidazole-1-yl)pyridine；2,6-di(imidazol-1-yl)pyridine
• CAS: 39242-17-6
• 化学式: C₁₁H₉N₅
• 分子量: 211.226
• InChiKey: RCULXUVDZWMPAS-UHFFFAOYSA-N

物化性质

• 沸点：
  481.8±30.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P264,P280,P302+P352+P332+P313+P362+P364,P305+P351+P338+P337+P313
• 危险性描述：
  H315,H319
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  2,6-二-(1-咪唑)吡啶 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  Cu（I）和Au（I）络合物中2,6-双（2-（二苯基膦基）-1H-咪唑-1-基）吡啶的多功能配位模式

  摘要：

  描述了咪唑基双膦[2,6-（PPh 2 C 3 H 2 N 2）2 C 5 H 3 N]的合成以及铜（I）和金（I）配合物。[2,6-（PPh 2 C 3 H 2 N 2）2 C 5 H 3 N]与一当量的CuX（X = Cl，Br或I）的反应生成单体[{2,6- {PPh 2 C 3 H 2 N 2 } 2 C 5 H 3 N} {CuI}]，二聚体[{PPh 2C 3 H 2 N 2 } 2 C 5 H 3 N} {CuCl}] 2，或一维​​（1D）聚合物[{2,6-（PPh 2 -C 3 H 2 N 2）2 C 5 H 3 N} {Cu 3 Br 2 }] n Cl配合物。配位聚合物[{2,6-（PPh 2 C 3 H 2 N 2）2 C 5 H 3 N} {Cu 3 Br 2 }]n Cl是包含具有四面体和线性几何形状的交替排列的铜原子的罕见实例。重复单元由来自两个配体的咪唑基氮

  DOI：

  10.1002/ejic.202000520
• 作为产物：
  描述：

  咪唑 、 2,6-二氯吡啶 在 氢氧化钾 、 四丁基溴化铵 作用下， 生成 2,6-二-(1-咪唑)吡啶
  参考文献：
  名称：

  桥接功能化双（N-杂环卡宾）配体的双核金（I）和金（III）配合物：合成，结构，光谱和电化学表征。

  摘要：

  我们报告了Au（I）和Au（III）配合物的合成，涉及醇官能化的双（N-杂环卡宾）配体。两条短的反应路径导致二咪唑前体，即1,1'-（2,6-吡啶二基）双[3-（2-羟乙基）-1H-咪唑-3-基]二碘化物（），3,3'（甲二基）双[1-（2-羟基-2-甲基丙基）-1H-咪唑-3-鎓]二溴化物（）和3,3'-（1,3-丙二基）双[1-（2-羟基-2） -甲基丙基）-1H-咪唑-3-基双（4-甲基乙基苯磺酸盐）（），其中两个重氮环被刚性吡啶单元或脂族链（C1或C3）桥接。Au（I）络合物[AuI（Lpy）] 2（2 +）[PF6-] 2（）和[AuI（LC1）] 2（2 +）[PF6-] 2（）通过直接金属化获得盐和分别在乙酸钠与Au（SMe（2））Cl存在下，然后在KPF6存在下进行阴离子复分解反应。三亚甲基化合物[AuI（LC3）] 2（2 +）[PF6-] 2（）是通过相关前体[AgI（LC3）]

  DOI：

  10.1039/b809943j

文献信息

• Linear and macrocyclic ligands containing alternating pyridine and imidazolidin-2-one units 1
  作者：Otto Meth-Cohn、Zegui Yan

  DOI：10.1039/a707131k

  日期：——

  Linear oligomers of alternating 2,6-disubstituted pyridine (P) and N,N′-disubstituted imidazolidine-2-one (I) units have been made rapidly and in high yield with up to nine repeating units, terminating in either pyridine or imidazolidin-2-one units, or one of each. Synthetic methods include: (1) the sodium hydride-mediated condensation of N-(tert-butyl)imidazolidin-2-one with 2,6-difluoropyridine (F-P-F) or with higher analogues such as F-PIP-F, to give IPI, IPIPI and IPIPIPI. (The tert-butyl protection is readily and quantitatively removed with acid.) (2) The caesium fluoride catalysed interaction of N,N′-[dimethyl-(1,1,3-trimethylpropyl)]-protected IPI with But-IP-F sequentially leads firstly to IPIPIPI which by the same method reacts with F-P-F to give F-PIPIPIPIP-F. (3) F-P-F also reacts with 1,2-ethylenediamine (E) sequentially to give F-PEP-F, EPEPE and F-PEPEPEP-F while similar reactions starting from F-PIP-F give EPIPE and F-PEPIPEP-F in sequence. Alternative routes examined include: (1) the interaction of F-P-F with imidazole to give 2,6-bis(imidazol-1-yl)pyridine and salts therefrom followed by (unsuccessful) oxidation. (2) The reaction of 2,6-diaminopyridine with 2-chloroethyl isocyanate followed by cyclisation to give IPI. (3) The interaction of 2,6-diaminopyridine with oxalate esters (O) to give OPO or H2N-POP-NH2, the latter of which was reduced to H2N-PEP-NH2.Cyclisation of the linear assemblies was not successful. However macrocyclic systems were made by linking two IPI units with two ethoxyethyl or with two ethoxyethoxyethyl units. Also two F-PIP-F units were similarly reacted to give polyether-linked macrocycles. Mono- and bis-prop-2-ynylated IPI derivatives were made but could not be cyclised. Attempts to cyclise ethylenediamine and oxamide based systems were also unsuccessful. The linear and macrocyclic ligands showed calcium selectivity in a study of their metal complexing abilities.

  交替的2,6-二取代吡啶（P）和N,N′-二取代咪唑烷-2-酮（I）单元的线性低聚物已被迅速制备并获得高产率，最多可达九个重复单元，以吡啶或咪唑烷-2-酮单元之一或两者之一结束。合成方法包括：（1）N-(叔丁基)咪唑烷-2-酮与2,6-二氟吡啶（F-P-F）或更高类似物如F-PIP-F的钠氢化物介导的缩合反应，得到IPI、IPIPI和IPIPIPI。（叔丁基保护基可轻松且定量地通过酸去除。）（2）N,N′-[二甲基-(1,1,3-三甲基丙基)]保护的IPI与But-IP-F的氟化铯催化相互作用首先导致IPIPIPI，通过相同方法与F-P-F反应得到F-PIPIPIPIP-F。（3）F-P-F还与1,2-乙二胺（E）连续反应得到F-PEP-F、EPEPE和F-PEPEPEP-F，而从F-PIP-F开始的类似反应依次得到EPIPE和F-PEPIPEP-F。考察的其他路线包括：（1）F-P-F与咪唑相互作用得到2,6-双(咪唑-1-基)吡啶及其盐，随后进行（不成功的）氧化。（2）2,6-二氨基吡啶与2-氯乙基异氰酸酯反应，然后环化得到IPI。（3）2,6-二氨基吡啶与草酸酯（O）相互作用得到OPO或H2N-POP-NH2，后者被还原为H2N-PEP-NH2。线性聚合物的环化未成功。然而，通过两个IPI单元与两个乙氧基乙基或两个乙氧基乙氧基乙基单元的连接制备了大环体系。同样，两个F-PIP-F单元反应得到聚醚连接的大环。制备了单和双-丙-2-炔基化的IPI衍生物，但无法环化。尝试环化乙二胺和草酰胺基系统也不成功。线性和大环配体在金属配位能力研究中显示出对钙的选择性。
• Selective palladium-catalysed arylation of 2,6-dibromopyridine using N-heterocyclic carbene ligands
  作者：D. Prajapati、C. Schulzke、M. K. Kindermann、A. R. Kapdi

  DOI：10.1039/c5ra10561g

  日期：——

  A selective palladium-catalysed arylation of 2,6-dibromopyridine has been developed by employing N-heterocyclic carbene ligands. Selective mono-arylation was performed in water/acetonitrile solvent system at ambient temperature with catalyst loading of 0.1 mol%. This reaction was also found to proceed smoothly in water although at a slightly elevated temperature of 80 °C. 2,6-Disubstituted and diversely

  通过使用N-杂环卡宾配体已经开发了钯的2,6-二溴吡啶的选择性芳基化。选择性单芳基化反应是在水/乙腈溶剂体系中于室温下以0.1 mol％的催化剂负载量进行的。尽管在稍高的80℃温度下，也发现该反应在水中能顺利进行。还以高收率获得了2，6-二取代的和被不同取代的2，6-吡啶，这对于有机和药物化学家将是重要的。
• Use of Acylhydrazine- and Acylhydrazone-Type Ligands to Promote CuI-Catalyzed C-N Cross-Coupling Reactions of Aryl Bromides with N-Heterocycles
  作者：Liuyi Li、Lei Zhu、Dagui Chen、Xuelei Hu、Ruihu Wang

  DOI：10.1002/ejoc.201100112

  日期：2011.5

  A series of ten acylhydrazine- and acylhydrazone-type ligands were designed and synthesized. Their electronic and steric properties were easily modified and tuned by varying the substituents in the vicinity of the acylhydrazine and acylhydrazone units. The effect of ligands on the catalytic activity of Ullmann reactions was assessed by using a combination of these ligands with CuI. The catalytic system

  设计并合成了一系列十个酰基肼和酰基腙型配体。通过改变酰基肼和酰基腙单元附近的取代基，它们的电子和空间性质很容易被修改和调整。通过使用这些配体与 CuI 的组合来评估配体对 Ullmann 反应催化活性的影响。该催化体系对于唑类与芳基和杂芳基溴化物的 C-N 偶联反应非常有效。
• Heterobimetallic <i>N</i>-Heterocyclic Carbene Complexes: A Synthetic, Spectroscopic, and Theoretical Study
  作者：Thomas P. Pell、David J. D. Wilson、Brian W. Skelton、Jason L. Dutton、Peter J. Barnard

  DOI：10.1021/acs.inorgchem.6b00222

  日期：2016.7.18

  A new synthetic methodology has been developed for the preparation of heterobimetallic group 11 and group 12 complexes of a symmetrical bis-NHC “pincer” ligand. The synthetic route involved the initial preparation of a mononuclear [Au(NHC)2]+ complex with pendent imidazole moieties on the NHC ligands. Subsequent alkylation of the imidazole groups with Et3OBF4 and metalation with a second metal ion

  已经开发出一种新的合成方法，用于制备对称双-NHC“钳子”配体的异双金属第11族和第12族配合物。合成途径涉及初步制备在NHC配体上具有咪唑侧基的单核[Au（NHC）2 ] +复合物。咪唑基随后用Et 3 OBF 4烷基化，并用第二种金属离子（Ag（I）或Hg（II））金属化，提供了两个杂双金属配合物。四homobimetallic（铜（I）2，银（I）2，金（I）2和Hg（II）2）相同的配合物双还制备了-NHC“钳”配体。均双金属Cu（I）2，Au（I）2和Hg（II）2配合物以及异双金属Au（I）-Ag（I）和Au（I）-Hg（II）配合物以及杂双金属的合成中间体配合物通过X射线晶体学表征。这些X射线结构表明，双金属配合物在固态中采用“扭曲”构象，支持短的M··M相互作用。同双金属Ag（I）2和Au（I）2的晶体样品 以及在室温和77 K下均能发射出杂双金属Au（I）-Ag（I）和A
• [EN] CATALYSTS FOR THE TRANSFORMATION OF CARBON DIOXIDE AND GLYCEROL TO FORMIC ACID AND LACTIC ACID AND METHODS OF MAKING THE SAME<br/>[FR] CATALYSEURS POUR LA TRANSFORMATION DE DIOXYDE DE CARBONE ET DE GLYCÉROL EN ACIDE FORMIQUE ET EN ACIDE LACTIQUE ET LEURS PROCÉDÉS DE FABRICATION
  申请人：UNIV GEORGE WASHINGTON

  公开号：WO2018213821A1

  公开（公告）日：2018-11-22

  Catalysts and methods for transformation of glycerol and a carbon feedstock, such as CO2, a carbonate salt or a bicarbonate salt, are described herein. Homogeneous catalysts include compounds of formula M[NHC-R-linker]aLbXc, where M is a transition metal, NHC is an N-heterocyclic carbene ligand, R is an alkyl or aryl group, linker is a polar group, L is a neutral ligand, X is an anionic ligand, a ranges from 1-3, b ranges from 0-3, and c ranges from 0-3. Heterogeneous catalysts include a solid support with a catalytically active compound immobilized on the solid support, where the catalytically active compound has the formula M[NHC-R-linker]aLbXc where M is a transition metal, NHC is an N-heterocyclic carbene ligand, R is an alkyl or aryl group; linker is a polar group, L is a neutral ligand, X is an anionic ligand, a ranges from 1-3, b ranges from 0-3, and c ranges from 0-3.

  本文描述了用于转化甘油和碳原料（如CO2、碳酸盐或碳酸氢盐）的催化剂和方法。均相催化剂包括具有M[NHC-R-linker]aLbXc式化合物的化合物，其中M是过渡金属，NHC是N-杂环卡宾配体，R是烷基或芳基，linker是极性基团，L是中性配体，X是阴离子配体，a范围为1-3，b范围为0-3，c范围为0-3。非均相催化剂包括具有固体支撑物的催化活性化合物固定在固体支撑物上，其中催化活性化合物具有M[NHC-R-linker]aLbXc式化合物，其中M是过渡金属，NHC是N-杂环卡宾配体，R是烷基或芳基；linker是极性基团，L是中性配体，X是阴离子配体，a范围为1-3，b范围为0-3，c范围为0-3。