1,3-二甲氧基-2-(3-吡啶基)苯 | 334977-38-7

• 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
• 中文名称: 1,3-二甲氧基-2-(3-吡啶基)苯
• 英文名称: 3-(2,6-dimethoxyphenyl)-pyridine
• 英文别名: 3-(2,6-Dimethoxyphenyl)pyridine
• CAS: 334977-38-7
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: IBBNRNHGBYIJKY-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  295.3±25.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：

  1,3-二甲氧基-2-(3-吡啶基)苯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,3-dimethoxy-2-(tol-2-yl)-4-bromobenzene 为溶剂， 生成 1,3-dimethoxy-2-(pyrid-3-yl)-4-bromobenzene
  参考文献：
  名称：

  Electron-deficient nitrogen heterocycle-substituted fluorescein dyes

  摘要：

  这项发明提供了含有电子亏缺氮杂环取代基的荧光素染料组合物，以及将这些染料与基质结合并用作分子生物学实验中的检测标记的方法。电子亏缺氮杂环包括吡啶、喹啉、吡嗪等。基质包括多核苷酸、核苷、核苷酸、肽、蛋白质、碳水化合物和配体。

  公开号：

  US06221604B1
• 作为产物：
  描述：

  3-溴吡啶 、 2,6-二甲氧基苯硼酸 以 1,3-Dimethoxy-2-(tol-2-yl)-benzene 为溶剂， 生成 1,3-二甲氧基-2-(3-吡啶基)苯
  参考文献：
  名称：

  Electron-deficient nitrogen heterocycle-substituted fluorescein dyes

  摘要：

  这项发明提供了含有电子亏缺氮杂环取代基的荧光素染料组合物，以及将这些染料与基质结合并用作分子生物学实验中的检测标记的方法。电子亏缺氮杂环包括吡啶、喹啉、吡嗪等。基质包括多核苷酸、核苷、核苷酸、肽、蛋白质、碳水化合物和配体。

  公开号：

  US06221604B1

文献信息

• Room-Temperature Suzuki-Miyaura Coupling of Heteroaryl Chlorides and Tosylates
  作者：Junfeng Yang、Sijia Liu、Jian-Feng Zheng、Jianrong Steve Zhou

  DOI：10.1002/ejoc.201200918

  日期：2012.11

  Suzuki–Miyaura coupling of heteroaryls is an important method for the preparation of compound libraries for medicinal chemistry and materials research. Although many catalysts have been developed, none of them have been generally applicable to the coupling reactions of heteroaryl chlorides and tosylates at room temperature. We discovered that a catalyst combination of Pd(OAc)2 and XPhos (2-dicyclohexylphosphanyl-2′

  杂芳基的 Suzuki-Miyaura 偶联是制备用于药物化学和材料研究的化合物库的重要方法。尽管已经开发了许多催化剂，但它们都没有普遍适用于杂芳基氯与甲苯磺酸酯在室温下的偶联反应。我们发现 Pd(OAc)2 和 XPhos（2-二环己基膦酰基-2',4',6'-三异丙基联苯）的催化剂组合可以有效地催化这些偶联。除了催化剂的选择，在含水醇溶剂中使用氢氧化物碱对于快速偶联也是必不可少的。这些条件促进了活性催化剂（XPhos）Pd0 的快速释放，并加速了催化循环中的金属转移。大多数杂芳基氯（31 个实例）和甲苯磺酸盐（17 个实例）的主要家族在室温下在几分钟到几小时内达到完全转化。该方法可以很容易地扩大规模以进行克级合成。此外，我们检查了整个反应中偶联伙伴的相对反应性。富电子杂芳基氯化物和甲苯磺酸盐的反应速度比缺电子杂芳基化合物慢，顺序为吲哚、吡咯呋喃、噻吩>吡啶。类似地，缺电子芳基硼酸的反应
• Catalysts for Suzuki−Miyaura Coupling Processes:  Scope and Studies of the Effect of Ligand Structure
  作者：Timothy E. Barder、Shawn D. Walker、Joseph R. Martinelli、Stephen L. Buchwald

  DOI：10.1021/ja042491j

  日期：2005.4.1

  catalyst levels, to prepare extremely hindered biaryls and to be carried out, in general, for reactions of aryl chlorides at room temperature. Additionally, structural studies of various 1.Pd complexes are presented along with computational data that help elucidate the efficacy that 1 imparts on Suzuki-Miyaura coupling processes. Moreover, a comparison of the reactions with 1 and with 2-(2',4',6'-t

  芳基和杂芳基卤化物与芳基-、杂芳基-和乙烯基硼酸的 Suzuki-Miyaura 偶联反应使用 2-(2',6'-二甲氧基联苯) 二环己基膦 SPhos (1) 以非常好的收率进行。这种配体为这些过程提供了前所未有的活性，允许在低催化剂水平下进行反应，制备极受阻的联芳基化合物，并且通常在室温下进行芳基氯的反应。此外，还介绍了各种 1.Pd 配合物的结构研究以及有助于阐明 1 对 Suzuki-Miyaura 偶联过程的功效的计算数据。此外，与 1 和 2-(2',4',6' -三异丙基联苯）二苯基膦（2）在确定配体体积和给电子能力在源自此类配体的催化剂的高活性中的相对重要性方面提供了信息。此外，当芳基溴变得太受阻时，一个有趣的 CH 键官能化-交叉偶联序列会介入以提供高产率的产物。
• Palladium-catalyzed decarboxylative coupling of aromatic acids with aryl halides or unactivated arenes using microwave heating
  作者：Adelina Voutchkova、Abigail Coplin、Nicholas E. Leadbeater、Robert H. Crabtree

  DOI：10.1039/b813998a

  日期：——

  Microwave heating greatly accelerates Pd-catalyzed decarboxylative coupling of aromatic acids and aryl iodides, and allows the coupling of benzoic acids with unactivated arenes.

  微波加热极大地加速了钯催化的芳族酸和芳基碘化物的脱羧偶联，并使苯甲酸与未活化的芳烃偶联。
• Electron-Rich Trialkyl-Type Dihydro-KITPHOS Monophosphines: Efficient Ligands for Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling. Comparison with Their Biaryl-Like KITPHOS Monophosphine Counterparts
  作者：Simon Doherty、Julian G. Knight、Nicholas A. B. Ward、Dror M. Bittner、Corinne Wills、William McFarlane、William Clegg、Ross W. Harrington

  DOI：10.1021/om3011992

  日期：2013.3.25

  The Diels-Alder cycloaddition between dicyclohexylvinylphosphine oxide and anthracene or 9-methylanthracene affords the bulky electron-rich trialkyl-type dihydro-KITPHOS monophosphines 11-(dicyclohexylphosphinoyl)-12-phenyl-9,10-dihydro-9,10-ethenoanthracene and 11-(dicyclohexylphosphinoyl)-9-methyl-12-phenyl-9,10-dihydro-9,10-ethenoanthracene, respectively, after reduction of the corresponding oxide. Both phosphines are highly air-sensitive and rapidly oxidize on silica gel during purification but have been isolated as air-stable cyclometalated palladium precatalysts of the type [Pdkappa(2)N2',C1-2-(2'-NH2C6H4)C6H4}Cl(L)]. Both palladium precatalysts form highly active systems for the Suzuki-Miyaura cross-coupling of a range of aryl chlorides with aryl boronic acids, giving the desired products in good to excellent yield under mild conditions and a catalyst loading of 0.25 mol %. A comparison of the performance of catalysts based on dihydro-KITPHOS monophosphines against their first-generation biaryl-like KITPHOS counterparts revealed that the latter are consistently more efficient for the vast majority of substrate combinations examined, albeit by only a relatively small margin in some cases. This, together with the greater air stability and ease of handling of biaryl-like KITPHOS monophosphines, renders them more practical ligands for palladium-based cross-coupling. The steric parameters of both classes of KITPHOS monophosphine and a selection of electron-rich biaryl monophosphines have been quantified using a combination of Solid-G to determine the percentage of the metal coordination sphere shielded by the phosphine (the G parameter), and Salerno molecular buried volume calculations (SambVca) to determine the percent buried volume (%V-bur); the corresponding Tolman cone angles have also been determined from correlations and the relative merits of the two approaches discussed. The electronic properties of these phosphines have also been investigated using DFT to calculate the A(1) nu(CO) frequency in LNi(CO)(3) (B3LYP/6-31G(2d,p)[LanL2DZ on Ni]), and the resulting computed electronic parameters (CEP) were used to estimate the corresponding experimental Tolman electronic parameters (TEP).
• USRE039663E1
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  公开号：——

  公开（公告）日：——