2-(3,5-dimethoxyphenyl)pyridine

• 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: 2-(3,5-dimethoxyphenyl)pyridine
• 英文别名: 2-(3,5-Dimethoxyphenyl)pyridine
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: PRSKEZLGWFMRRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,5-dimethoxyphenyl)pyridine 在 potassium tert-butylate 、 sodium methylate 、 三溴化硼 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.33h， 生成 6-[3-(4-methylsulfonylphenoxy)-5-propan-2-yloxyphenyl]-1H-pyridin-2-one
  参考文献：
  名称：

  Pyrimidone-based series of glucokinase activators with alternative donor–acceptor motif

  摘要：

  Glucokinase activators are a class of experimental agents under investigation as a therapy for Type 2 diabetes mellitus. An X-ray crystal structure of a modestly potent agent revealed the potential to substitute the common heterocyclic amide donor-acceptor motif for a pyridone moiety. We have successfully demonstrated that both pyridone and pyrimidone heterocycles can be used as a potent donor-acceptor substituent. Several sub-micromolar analogs that possess the desired partial activator profile were synthesized and characterized. Unfortunately, the most potent activators suffered from sub-optimal pharmacokinetic properties. Nonetheless, these donor-acceptor motifs may find utility in other glucokinase activator series or beyond. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.036
• 作为产物：
  描述：

  2-溴吡啶 、 1-溴-3,5-二甲氧基苯 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以58%的产率得到2-(3,5-dimethoxyphenyl)pyridine
  参考文献：
  名称：

  钯催化2-苯基吡啶与烷基碘化物的CH烷基化

  摘要：

  已成功开发了钯催化的2-苯基吡啶与烷基碘的CH烷基化反应。从2-苯基吡啶得到的palladacycles应该作为烷基化反应中的关键中间体。

  DOI：

  10.1039/c7ob01232b

文献信息

• A facile synthetic route for 2-pyridyl derivatives: direct preparation of a stable 2-pyridylzinc bromide and its copper-free and pd-catalyzed coupling reactions
  作者：Seung-Hoi Kim、Reuben D. Rieke

  DOI：10.1016/j.tetlet.2009.07.004

  日期：2009.9

  Direct preparation of 2-pyridylzinc bromide has been developed. Interestingly, the subsequent coupling reactions with acid chlorides have been carried out without any transition metal catalyst. 2-Pyridylaryl compounds, symmetrical and unsymmetrical 2,2′-bipyridines were also successfully obtained from palladium-catalyzed coupling reactions of 2-pyridylzinc bromide under mild conditions.

  已经开发了直接制备2-吡啶基溴化锌的方法。有趣的是，随后与酰氯的偶联反应已经在没有任何过渡金属催化剂的情况下进行了。还可以从钯催化的2-吡啶基溴化锌在温和条件下的偶联反应中成功获得2-吡啶基芳基化合物，对称和不对称的2,2'-联吡啶。
• 2-Pyridyl and 3-pyridylzinc bromides: direct preparation and coupling reaction
  作者：Seung-Hoi Kim、Reuben D. Rieke

  DOI：10.1016/j.tet.2010.02.061

  日期：2010.4

  A facile synthetic approach to the direct preparation of 2-pyridyl and 3-pyridylzinc bromides has been demonstrated using Rieke zinc with 2-bromopyridine and 3-bromopyridine, respectively. A variety of different electrophiles have been coupled with the resulting organozinc reagents to give the corresponding cross-coupling products in moderate to good yields.

  已证明使用Rieke锌分别与2-溴吡啶和3-溴吡啶直接合成2-吡啶基和3-吡啶基锌溴化物的简便合成方法。各种不同的亲电试剂已与所得的有机锌试剂偶联，以中等至良好的产率得到相应的交叉偶联产物。
• A novel and robust heterogeneous Cu catalyst using modified lignosulfonate as support for the synthesis of nitrogen-containing heterocycles
  作者：Bingbing Lai、Meng Ye、Ping Liu、Minghao Li、Rongxian Bai、Yanlong Gu

  DOI：10.3762/bjoc.16.238

  日期：——

  A waste biomass, sodium lignosulfonate, was treated with sodium 2-formylbenzenesulfonate, and the phenylaldehyde condensation product was then used as a robust supporting material to immobilize a copper species. The so-obtained catalyst was characterized by many physicochemical methods including FTIR, EA, FSEM, FTEM, XPS, and TG. This catalyst exhibited excellent catalytic activity in the synthesis

  用2-甲酰基苯磺酸钠处理废生物质木质素磺酸钠，然后将苯醛缩合产物用作坚固的支撑材料，以固定铜物种。如此获得的催化剂通过许多物理化学方法进行了表征，包括FTIR，EA，FSEM，FTEM，XPS和TG。该催化剂在合成含氮杂环（例如带有3,4-稠合七元环，2-芳基吡啶，氨基萘和3-苯基异喹啉的三环吲哚）中表现出出色的催化活性。另外，该催化剂显示出可回收利用，并且可以在反应过程中多次重复使用而活性没有明显损失。
• A Mixed Ligand Approach for the Asymmetric Hydrogenation of 2-Substituted Pyridinium Salts
  作者：Marc Renom-Carrasco、Piotr Gajewski、Luca Pignataro、Johannes G. de Vries、Umberto Piarulli、Cesare Gennari、Laurent Lefort

  DOI：10.1002/adsc.201600348

  日期：2016.8.18

  describe a new methodology for the asymmetric hydrogenation (AH) of 2‐substituted pyridinium salts. An iridium catalyst based on a mixture of a chiral monodentate phosphoramidite and an achiral phosphine was shown to hydrogenate N‐benzyl‐2‐arylpyiridinium bromides to the corresponding N‐benzyl‐2‐arylpiperidines with full conversion and good enantioselectivity. The mechanism of the reaction under optimized

  在这里，我们描述了一种新的方法用于2取代的吡啶鎓盐的不对称氢化（AH）。结果表明，基于手性单齿亚磷酰胺和非手性膦的混合物的铱催化剂可将N -2-苄基-2-芳基吡啶鎓溴化物氢化为相应的N -2-苄基-2-芳基哌啶，具有完全的转化率和良好的对映选择性。通过动力学测量和同位素标记实验研究了在最佳条件下的反应机理。我们的研究表明，氢化反应从添加1,4-氢化物开始，对映异构步骤涉及亚胺基中间体的还原。
• 2-Arylpyridines from 2-pyridylcopper/triphenylphosphine and iodoarenes
  作者：Hans Malmberg、Martin Nilsson

  DOI：10.1016/s0040-4020(01)87553-0

  日期：1986.1

  2-Arylpyridines are formed rather selectively in 50 to 80 % yields from 2-pyridylcopper and unactivated iodoarenes in the presence of one to two mol triphenylphosphine in toluene around 100 °C. The selectivity may be due to the ability of the copper(I) iodide-triphenylphosphine complex as a leaving group or may be discussed in terms of oxidative addition/reductive elimination. The unsymmetric coupling

  在1至2摩尔三苯基膦在甲苯中约100°C的条件下，由2-吡啶基铜和未活化的碘代芳烃以50至80％的收率选择性地形成2-芳基吡啶。选择性可能是由于碘化亚铜（I）-三苯基膦配合物作为离去基团的能力，或者可能是通过氧化加成/还原消除来讨论的。由于苯基铜/三苯基膦与2-碘吡啶的偶合也产生了2-苯基吡啶，因此不对称偶合反应可能是普遍的。