(6-methoxypyridin-3-yl)(phenyl)methanone | 32401-36-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6-methoxypyridin-3-yl)(phenyl)methanone
• 英文别名: (6-Methoxypyridin-3-yl)(phenyl)methanone；(6-methoxypyridin-3-yl)-phenylmethanone
• CAS: 32401-36-8
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: NUGXNQPBORDCFD-UHFFFAOYSA-N

物化性质

• 沸点：
  347.6±27.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

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：
  0.08
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6-methoxypyridin-3-yl)(phenyl)methanone 在 Ru(R,R)teth-TsDPEN 、 三乙胺 作用下， 以 甲酸 为溶剂， 反应 24.0h， 以48%的产率得到
  参考文献：
  名称：

  Synthesis and reduction reactions of pyridones and 5-acyl-2-methoxypyridines

  摘要：

  The synthesis of a series of pyridones, from their 2-hydroxypyridine or 2-methoxypyridine precursors, is described, along with studies into their reductions to saturated heterocycles. A number of 5-acylpyridones were prepared and were evaluated as substrates for asymmetric transfer hydrogenation prior to conversion to saturated heterocycles. The enantioselective reduction of 5-acetyl-1-benzylpyrimidine-2,4(1H,3H)-dione is also described. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.046
• 作为产物：
  描述：

  苯甲酸 在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium phosphate 、 正丁基锂 、 草酰氯 、 1,1'-((2,4,6-trimethyl-1,3-phenylene)bis(methylene))bis(3-(2,6-diisopropylphenyl)-1H-imidazol-3-ium) chloride 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 27.17h， 生成 (6-methoxypyridin-3-yl)(phenyl)methanone
  参考文献：
  名称：

  Ni- N-酰基吡咯型酰胺与有机硼试剂的镍催化交叉偶联反应

  摘要：

  酰胺向酮的催化转化是非常需要的，但是在有机合成中具有挑战性。我们在此报道了N-酰基吡咯型酰胺与芳基硼酸酯的第一次Ni /双-NHC催化的交叉偶联，以获得二芳基酮。新的螯合双-NHC配体促进了该方法。该反应耐受芳基酰胺和芳基硼酸酯伙伴上的各种官能团，包括敏感的酯基和酮基。

  DOI：

  10.1039/c7cc07457c

文献信息

• General Method for the Suzuki–Miyaura Cross-Coupling of Primary Amide-Derived Electrophiles Enabled by [Pd(NHC)(cin)Cl] at Room Temperature
  作者：Peng Lei、Guangrong Meng、Yun Ling、Jie An、Steven P. Nolan、Michal Szostak

  DOI：10.1021/acs.orglett.7b03191

  日期：2017.12.15

  temperature Suzuki–Miyaura cross-coupling of commonly encountered primary benzamides is reported. A combination of site-selective N,N-di-Boc-activation (tert-butoxycarbonyl activation) of the amide nitrogen with practical air- and moisture-stable, well-defined, and highly reactive [Pd(NHC)(cin)Cl] (NHC = N-heterocyclic carbene; cin = cinnamyl) provides a highly effective route to biaryl ketones from primary

  据报道，室温下，通常遇到的主要苯甲酰胺的Suzuki-Miyaura交叉偶联是一种通用的，高度选择性的方法。酰胺氮的位点选择性N，N -di-Boc活化（叔丁氧基羰基活化）与稳定的空气和水分稳定的，定义明确的和高反应性的[Pd（NHC）（cin）Cl ]（NHC = N-杂环卡宾； cin =肉桂基）提供了一种从伯酰胺高收率制备联芳基酮的高效途径。酰胺酰基交叉偶联首次获得了> 1000的TON。
• Acylboronates in Polarity-Reversed Generation of Acyl Palladium(II) Intermediates
  作者：Alina Trofimova、Aleksandra Holownia、Chieh-Hung Tien、Martynas J. Širvinskas、Andrei K. Yudin

  DOI：10.1021/acs.orglett.1c00742

  日期：2021.5.7

  process between aryl (pseudo)halides and boron-based acyl anion equivalents. This mode of acylboronate reactivity represents polarity reversal, which is supported by the observation of tetracoordinated boronate and acyl palladium(II) species by 11B, 31P NMR, and mass spectrometry. A broad scope of aliphatic and aromatic acylboronates has been examined, as well as a variety of aryl (pseudo)halides.

  我们报告芳基（假）卤化物和硼基酰基阴离子当量之间的催化交叉偶联过程。酰基硼酸酯反应性的这种模式表示极性反转，这通过11 B，31 P NMR和质谱观察到四配位的硼酸酯和酰基钯（II）物种得到支持。已经研究了广泛范围的脂族和芳族酰基硼酸酯，以及各种芳基（假）卤化物。
• Triflamides: Highly Reactive, Electronically Activated <i>N</i>-Sulfonyl Amides in Catalytic N–C(O) Amide Cross-Coupling
  作者：Shicheng Shi、Roger Lalancette、Roman Szostak、Michal Szostak

  DOI：10.1021/acs.orglett.8b03901

  日期：2019.3.1

  The direct, highly chemoselective Suzuki–Miyaura cross-coupling of trifluoromethanesulfonamides (triflamides) by selective N–C(O) amide bond cleavage is reported. This operationally simple, mild, and user-friendly method accomplishes the direct synthesis of ketones from amides by a catalytic manifold as a powerful alternative to Weinreb amides. Mechanistic studies support rotational inversion and electronic

  据报道，通过选择性的N-C（O）酰胺键裂解，直接，高度化学选择性的Suzuki-Miyaura交叉偶联了三氟甲磺酰胺（三氟化物）。这种操作简单，温和且用户友好的方法通过催化歧管完成了从酰胺直接合成酮的方法，可作为Weinreb酰胺的强大替代品。机理研究支持旋转反转和电子激活，有利于在温和条件下选择性插入。我们的数据强烈暗示三氟化物应常规视为酰胺键交叉偶联的前体。
• Heteroaryl manganese reagents: direct preparation and reactivity studies
  作者：Reuben D. Rieke、YoungSung Suh、Seung-Hoi Kim

  DOI：10.1016/j.tetlet.2005.06.092

  日期：2005.8

  Direct preparation of various heteroaryl manganese reagents was performed by using highly active manganese (Mn∗) and heteroaryl halides. The resulting organomanganese reagents were coupled with electrophiles such as aryl halides, vinyl halides, and benzoyl chlorides under mild reaction conditions. The corresponding coupling products were obtained in good yields.

  使用高活性锰（Mn *）和杂芳基卤化物可以直接制备各种杂芳基锰试剂。在温和的反应条件下，将所得的有机锰试剂与亲电试剂（例如芳基卤化物，乙烯基卤化物和苯甲酰氯）偶联。以良好的产率获得了相应的偶联产物。
• Synthesis and reduction reactions of pyridones and 5-acyl-2-methoxypyridines
  作者：Alexander A. Bisset、Allan Dishington、Teyrnon Jones、Guy J. Clarkson、Martin Wills

  DOI：10.1016/j.tet.2014.06.046

  日期：2014.10

  The synthesis of a series of pyridones, from their 2-hydroxypyridine or 2-methoxypyridine precursors, is described, along with studies into their reductions to saturated heterocycles. A number of 5-acylpyridones were prepared and were evaluated as substrates for asymmetric transfer hydrogenation prior to conversion to saturated heterocycles. The enantioselective reduction of 5-acetyl-1-benzylpyrimidine-2,4(1H,3H)-dione is also described. (C) 2014 Elsevier Ltd. All rights reserved.