4-(o-tolyl)pyridine | 30456-66-7

• 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: 4-(o-tolyl)pyridine
• 英文别名: 4-(2-methylphenyl)pyridine
• CAS: 30456-66-7
• 化学式: C₁₂H₁₁N
• mdl: MFCD00657927
• 分子量: 169.226
• InChiKey: WIMXAKQSDVSRIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(o-tolyl)pyridine 以 四氢呋喃 、 乙二醇乙醚 、 水 为溶剂， 反应 30.0h， 生成 Ir(2-phenyl-4-(o-tolyl)pyridine(-H))2(pic)
  参考文献：
  名称：

  有机锂试剂在合成4-芳基-2-苯基吡啶及其相应的铱（iii）配合物中的用途†

  摘要：

  据报道，从4-氧代哌啶-1-羧酸叔丁酯开始，合成4-芳基取代的苯基吡啶（ppy）的一种无钯的通用途径。与芳基锂反应，然后进行三氟乙酸脱水/脱保护，并与2-碘基苯甲酸氧化，最后进行苯基化，得到4个配体（L 1-4 H）：2,4-二苯基吡啶，4-（4-甲氧基苯基）-2-苯基吡啶，2-苯基-4-（邻甲苯基）吡啶和4-间甲苯基-2-苯基吡啶。这些配体与铱配位得到相应的Ir（L）2（A）络合物（Ir1–7），其中A =辅助配体乙酰乙酸盐或2-吡啶甲酸。这用于证明，通过辅助配体选择和ppy配体的4-芳基取代基之间的扭转扭曲的组合，可以在502-560 nm的范围内调节复合物的磷光发射。

  DOI：

  10.1039/c6dt01461e
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 在 palladium on activated charcoal 盐酸 、 正丁基锂 、 溶剂黄146 作用下， 以 邻二甲苯 为溶剂， 反应 23.5h， 生成 4-(o-tolyl)pyridine
  参考文献：
  名称：

  In vivo intracerebral microdialysis studies in rats of MPP+ (1-methyl-4-phenylpyridinium) analogs and related charged species

  摘要：

  The in vivo dopaminergic neurotoxic properties of 45 MPTP and MPP+ analogues and related compounds were examined by an intrastriatal microdialysis assay in conscious rats. MPP(+)-like toxicity, as evidenced by the irreversible effects on DA release and enhancement of lactate formation, was observed with a variety of structural types although no compound was more toxic than MPP+. The following global structure-toxicity relationships could be derived: (1) only permanently charged compounds showed neurotoxic effects; (2) with the exception of amino groups, hydrophilic substituents abolished toxicity; (3) activity was enhanced by lipophilic groups although increased steric bulk around the nitrogen atom tended to decrease activity; (4) nonaromatic, quaternary systems (methiodide of MPTP, guanidinium derivatives) were only weakly toxic; and (5) certain bi- and tricyclic systems, including putative metabolites of potential endogenous MPTP-like compounds, were weakly toxic. The lack of toxic effects following perfusions with DA itself confirmed that MPTP dopaminergic neurotoxicity is not likely to be mediated by the MPP(+)-induced release of DA. With some interesting exceptions, these in vivo data correlate reasonably well with in vitro data on the nerve terminal uptake properties and the inhibitory effects on mitochondrial respiration of these compounds.

  DOI：

  10.1021/jm00170a029

文献信息

• Microwave-Assisted Suzuki Coupling Reactions with an Encapsulated Palladium Catalyst for Batch and Continuous-Flow Transformations
  作者：Ian R. Baxendale、Charlotte M. Griffiths-Jones、Steven V. Ley、Geoffrey K. Tranmer

  DOI：10.1002/chem.200501400

  日期：2006.5.24

  This article describes the design, optimisation and development of a Suzuki cross-coupling protocol mediated by an efficient palladium-encapsulated catalyst (Pd EnCat) under microwave irradiation. The methodology has been used in both batch mode for classical library preparation and in continuous-flow applications furnishing multigram quantities of material. Described is a method that uses direct focused

  本文介绍了在微波辐射下由高效钯封装的催化剂（Pd EnCat）介导的Suzuki交叉偶联方案的设计，优化和开发。该方法已在批处理模式下用于经典文库制备，并已在连续流应用中使用，以提供数克的材料。描述了一种在施加外部冷却源的同时使用直接聚焦微波加热的方法。这使得可以在整个反应期间保持低于正常的总体温度，从而导致反应产物的总产率和纯度的显着提高。关于固定催化剂体系的延长寿命和增强的反应性，讨论了该新颖的加热方案的其他方面。
• Vesicular Monoamine Transporter Substrate/Inhibitor Activity of MPTP/MPP⁺ Derivatives: A Structure–Activity Study
  作者：D. Shyamali Wimalasena、Rohan P. Perera、Bruce J. Heyen、Inoka S. Balasooriya、Kandatege Wimalasena

  DOI：10.1021/jm070875p

  日期：2008.2.1

  number of MPTP and MPP(+) derivatives that are suitable for the comparative neurotoxicity and complex I inhibition versus dopamine metabolism perturbation studies. Structure-activity studies with bovine chromaffin granule ghosts show that 3'-hydroxy-MPP(+) is one of the best known substrates for the vesicular monoamine transporter (VMAT). A series of compounds that combine the structural features of

  1-甲基-4-苯基-1,2,3,6-四氢吡啶（MPTP），N-甲基-4-苯基吡啶（MPP（+））的活性代谢产物选择性破坏多巴胺能神经元并诱发帕金森氏症疾病。已经提出通过细胞和颗粒的积累来抑制线粒体复合物I和/或干扰多巴胺代谢是神经毒性的一些主要原因。在本研究中，我们已经合成并表征了许多MPTP和MPP（+）衍生物，这些衍生物适用于比较神经毒性和复合物I抑制与多巴胺代谢扰动研究。结构活性研究与牛嗜铬粒鬼魂表明3'-羟基-MPP（+）是水泡单胺转运蛋白（VMAT）的最知名的底物之一。结合MPP（+）和先前表征的VMAT抑制剂3-氨基-2-苯基-丙烯的结构特征的一系列化合物已被确定为最有效的VMAT抑制剂。这些衍生物已用于定义VMAT底物的结构要求和抑制剂活性。
• Phosphonium Salts as Pseudohalides: Regioselective Nickel‐Catalyzed Cross‐Coupling of Complex Pyridines and Diazines
  作者：Xuan Zhang、Andrew McNally

  DOI：10.1002/anie.201704948

  日期：2017.8.7

  traditional cross‐coupling methods. An alternative approach is presented where pyridines and diazines are converted into heteroaryl phosphonium salts and coupled with aryl boronic acids. Nickel catalysts are unique for selective heteroaryl transfer, and the reaction has a broad substrate scope that includes complex pharmaceuticals. Phosphonium ions also display orthogonal reactivity in cross‐couplings compared

  杂双芳基化合物是重要的药效团，很难通过传统的交叉偶联方法制备。提出了一种替代方法，其中将吡啶和二嗪转化为杂芳基phospho盐并与芳基硼酸偶联。镍催化剂对于选择性杂芳基转移是独特的，该反应具有广泛的底物范围，包括复杂的药物。与卤化物相比，离子在交叉偶联中也表现出正交反应性，从而实现化学选择性的钯和镍催化的偶联序列。
• METHOD FOR PRODUCING COMPOUND HAVING DEUTERATED AROMATIC RING OR HETEROCYCLIC RING
  申请人：Shimodaira Haruki

  公开号：US20100331540A1

  公开（公告）日：2010-12-30

  A method for producing a compound having a deuterated aromatic ring or heterocyclic ring according to the invention includes heating a compound having an aromatic ring or heterocyclic ring in the presence of heavy water, a transition metal and a metal which generates deuterium. As the metal which generates deuterium, at least one metal selected from the group consisting of aluminum, magnesium, zinc, iron, lead and tin is preferred. As the transition metal, at least one metal selected from the group consisting of platinum, palladium, ruthenium and rhodium is preferred. The heating is preferably carried out by microwave irradiation.

  根据本发明，生产具有氘代芳香环或杂环的化合物的方法包括在重水、过渡金属和产生氘的金属存在下加热具有芳香环或杂环的化合物。作为产生氘的金属，优选铝、镁、锌、铁、铅和锡中的至少一种金属。作为过渡金属，优选铂、钯、钌和铑中的至少一种金属。加热最好通过微波辐射进行。
• The pyridyl cation as a reactive intermediate in the photoreaction of iodopyridines with benzenes
  作者：Kazue Ohkura、Koh-ichi Seki、Masanao Terashima、Yuichi Kanaoka

  DOI：10.1016/s0040-4039(00)99264-5

  日期：1989.1

  The electrophilic behavior of the reactive entity in the phtosubstitution of benzenes with 2-iodopyridine was found to be ascribable to the intermediary 2-pyridyl cation, rather than to the electrophilic 2-pyridyl radical.

  发现苯在苯酚的光取代反应中，反应性实体的亲电子行为归因于中间的2-吡啶基阳离子，而不是归因于亲电子的2-吡啶基。