1-甲基-2-(2-吡啶基)吡啶碘化物 | 77972-47-5

• 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: 1-甲基-2-(2-吡啶基)吡啶碘化物
• 中文别名: N-甲基-2,2'-联吡啶碘化物
• 英文名称: 1-methyl-[2,2'-bipyridin]-1-ium iodide
• 英文别名: N-methyl-2,2'-bipyridinium iodide；1-Methyl-2-(2-pyridyl)pyridinium Iodide；1-methyl-2-pyridin-2-ylpyridin-1-ium;iodide
• CAS: 77972-47-5
• 化学式: C₁₁H₁₁N₂*I
• 分子量: 298.126
• InChiKey: PIKLCVQDBVTHFG-UHFFFAOYSA-M

物化性质

• 熔点：
  147.0 to 151.0 °C
• 最大波长(λmax)：
  277nm(H2O)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.42
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  16.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  室温且干燥

反应信息

• 作为反应物：
  描述：

  1-甲基-2-(2-吡啶基)吡啶碘化物 在 sodium hydroxide 、 溴 、 三苯基膦 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 33.0h， 生成 2-(6-Pyridin-2-ylpyridin-2-yl)acetonitrile
  参考文献：
  名称：

  Regioselective Functionalization of 2,2'-Bipyridine and Transformations into Unsymmetric Ligands for Coordination Chemistry.

  摘要：

  Novel synthetic strategies for a series of unsymmetrically substituted 2,2'-bipyridines have been developed. These bipyridines have found use in some novel homoleptic and heteroleptic ruthenium(II) complexes. Two methods for regiochemical control of nucleophilic addition to bpy have been explored: (i) mono N-oxidation followed by cyanation and subsequent hydrolysis gave 6-carboxy-2,2'-bipyridine (4); (ii) mono N-methylation followed by the conversion into 6-bromo-2,2'-bipyridine (12) and subsequent nucleophilic addition of lithio-acetonitrile followed by hydrolysis of 6-cyanomethyl-2,2'-bipyridine (8) gave the homologous 2,2'-bipyridine-6-acetic acid (9). An established method of regioselective mono-ring alkylation of bpy using methyllithium yielded 6-methyl-2,2'-bipyridine (14), and the generation of the anion of 14 and subsequent addition to a chloromethyl oxazoline was applied to synthesize a second homologue, methyl 2,2'-bipyridine-6-propanoate (16). Structural determinations using H-1, C-13 and 2D NMR spectroscopy permitted complete assignments of all signals in the H-1 NMR spectra.

  DOI：

  10.3891/acta.chem.scand.52-0077
• 作为产物：
  描述：

  2,2'-联吡啶 、 碘甲烷 以 乙腈 为溶剂， 反应 16.0h， 以60%的产率得到1-甲基-2-(2-吡啶基)吡啶碘化物
  参考文献：
  名称：

  吡啶的区域选择性直接CH三氟甲基化。

  摘要：

  基于N-甲基吡啶季铵活化策略，开发了一种高效且区域选择性的吡啶直接CH H三氟甲基化方法。通过在N，N-二甲基甲酰胺中在碳酸银存在下用三氟乙酸处理碘化吡啶鎓盐，可以以良好的产率和优异的区域选择性获得各种三氟甲基吡啶。该协议具有良好的功能组兼容性，易于获得的起始材料以及操作简便的特点。对照实验表明，该反应可能涉及亲核三氟甲基化机理。

  DOI：

  10.1021/acs.orglett.0c02413

文献信息

• A mechanistic study of transfer hydrogenation catalyzed by cyclometallated ruthenium half-sandwich complexes
  作者：Noor U. Din Reshi、Dineshchakravarthy Senthurpandi、Ashoka G. Samuelson

  DOI：10.1016/j.jorganchem.2018.04.028

  日期：2018.7

  Transfer hydrogenation of aromatic ketones catalyzed by eight cyclometallated ruthenium half-sandwich complexes, including three new complexes, was examined. The catalytic process was studied using different ratios of substrate to base and base to catalyst and using a deuterated reductant. Optimum conditions for catalysis were shown to be in the presence of higher amounts of base in refluxing isopropanol

  研究了由八个环金属化钌半三明治复合物（包括三个新的复合物）催化的芳族酮的转移加氢。使用不同比例的底物与碱以及碱与催化剂的比例以及氘化还原剂研究了催化过程。已表明最佳的催化条件是在回流的异丙醇中存在较高量的碱。在这些条件下，复合物就地还原使Ru（0）纳米粒子肉眼看不见。通过TEM，DLS和XPS对纳米颗粒进行了表征。发现在产生纳米颗粒的条件下的催化转移氢化远大于通过分子催化剂的转移氢化。对三种新的配合物进行了完整的表征，包括对这些配合物的X射线晶体学表征。
• Stereodivergent Synthesis of Alkenylpyridines via Pd/Cu Catalyzed C–H Alkenylation of Pyridinium Salts with Alkynes
  作者：Wenjing Li、Juan Tang、Shun Li、Xueli Zheng、Maolin Yuan、Bin Xu、Weidong Jiang、Haiyan Fu、Ruixiang Li、Hua Chen

  DOI：10.1021/acs.orglett.0c02679

  日期：2020.10.16

  The first Pd/Cu catalyzed selective C2-alkenylation of pyridines with internal alkynes has been developed via the pyridinium salt activation strategy. Importantly, the configuration of the product alkenylpyridines could be tuned by the choice of the proper N-alkyl group of the pyridinium salts, thus allowing for both the Z- and E-alkenylpyridines synthesized with good regio- and stereoselectivity.

  通过吡啶鎓盐活化策略已开发了具有内部炔烃的吡啶的第一个Pd / Cu催化的选择性C2-烯基化反应。重要的是，可以通过选择吡啶鎓盐的合适的N-烷基来调节产物烯基吡啶的构型，从而允许以良好的区域和立体选择性合成Z-和E-烯基吡啶。基于Hammett研究和KIE实验，提出了一个合理的机制。
• Binuclear bismuth halide complexes (N-Me(2,2'-BipyH))2[Bi2X10] (X = Cl, Br): Syntheses, crystal structures, and optical properties
  作者：S. A. Adonin、I. D. Gorokh、D. G. Samsonenko、I. V. Yushina、M. N. Sokolov、V. P. Fedin

  DOI：10.1134/s1070328416110014

  日期：2016.11

  Binuclear halide complexes (N-Me(2,2'-BipyH)2[Bi2X10] (X = Cl (I), Br (II); 2,2'-Bipy = 2,2'-bipyridine) are synthesized by the reaction of solutions of [BiX6]3– and (N-Me(2,2'-BipyH)(NO3)2 in 2 M HX. The structure of [Bi2X10]4– anions consists of octahedral fragments BiX6} linked by two μ2-bridging halide ligands. The structures of the compounds are determined by X-ray diffraction analysis (CIF files

  双核卤化物配合物（N -Me（2,2'-BipyH）2 [Bi 2 X 10 ]（X = Cl（I），Br（II）; 2,2'-Bipy = 2,2'-联吡啶）通过[BiX 6 ] 3–和（N -Me（2,2'-BipyH）（NO 3）2的溶液在2 M HX中的反应合成。[Bi 2 X 10 ] 4–阴离子的结构由八面体片段BIX 6 }由两个μ连接2 -bridging卤化物配位体。该化合物的结构通过X射线衍射分析测定的（CIF文件CCDC 1455987（I）和1455988（II））。从散射反射光谱确定复合物II的禁带宽度E g。
• Synthesis and structures of two mononuclear iron(ii) complexes derived from polypyridine ligands
  作者：Hongqiao Wang、Nan Wu、Jing Zheng、Chunyang Zheng、Dunjia Wang

  DOI：10.1016/j.mencom.2020.01.033

  日期：2020.1

  Three polypyridine ligands such as tri(2-pyridyl)methane, (2,2’-bipyridin-6-yl)di(2-pyridyl)methane and 2,6-bis[di(2-pyridyl)methyl] pyridine as well as their new iron(II) mononuclear complexes have been obtained in a one-pot synthesis. Detailed structural analyses and magnetic susceptibility measurements confirm the expected six-coordinate octahedral geometry and the metric parameters are consistent

  三个聚吡啶配体，例如三（2-吡啶基）甲烷，（2,2'-联吡啶-6-基）二（2-吡啶基）甲烷和2,6-双[二（2-吡啶基）甲基]吡啶因为它们的新铁（II）单核络合物是通过一锅法合成获得的。详细的结构分析和磁化率测量结果证实了预期的六坐标八面体几何形状，并且度量参数与配合物中的低旋铁（II）一致。
• Synthesis of new pyrrole–pyridine-based ligands using an in situ Suzuki coupling method
  作者：Matthias Böttger、Björn Wiegmann、Steffen Schaumburg、Peter G Jones、Wolfgang Kowalsky、Hans-Hermann Johannes

  DOI：10.3762/bjoc.8.116

  日期：——

  The compounds 6-(pyrrol-2-yl)-2,2‘-bipyridine, 2-(pyrrol-2-yl)-1,10-phenanthroline and 2-(2-(N-methylbenz[d,e]imidazole)-6-(pyrrol-2-yl)-pyridine were synthesized by using an in situ generated boronic acid for the Suzuki coupling. Crystals of the products could be grown and exhibited interesting structures by X-ray analysis, one of them showing a chain-like network with the adjacent molecules linked to each other via intermolecular N–H^…N hydrogen bonds.

  化合物6-(吡咯-2-基)-2,2'-联吡啉，2-(吡咯-2-基)-1,10-邻菲啰啉和2-(2-(N-甲基苯并[d,e]咪唑)-6-(吡咯-2-基)-吡啉是通过使用原位生成的硼酸进行铃木偶联合成的。通过X射线分析可以生长出产物的晶体，并展示出有趣的结构，其中之一显示出链状网络，相邻分子通过分子间N–H^…N氢键相互连接。