(4-methoxyphenyl)(pyrazin-2-yl)methanone | 86461-74-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-methoxyphenyl)(pyrazin-2-yl)methanone
• 英文别名: 2-Pyrazinyl-4-methoxyphenylketone；(4-methoxyphenyl)-pyrazin-2-ylmethanone
• CAS: 86461-74-7
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: WVSCPUBHPXOQBV-UHFFFAOYSA-N

物化性质

• 沸点：
  375.7±32.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-肼吡啶 、 (4-methoxyphenyl)(pyrazin-2-yl)methanone 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 以58%的产率得到N-[1-(4-Methoxy-phenyl)-1-pyrazin-2-yl-meth-(E)-ylidene]-N'-pyridin-2-yl-hydrazine
  参考文献：
  名称：

  Azinyl and Diazinyl Hydrazones Derived from Aryl N-Heteroaryl Ketones:  Synthesis and Antiproliferative Activity^,

  摘要：

  A series of N-heteroaryl hydrazones derived from aryl N-heteroaryl or bis-N-heteroaryl methanones was prepared in search for potential novel antitumor agents. The stereochemistry of these compounds was established by means of NMR spectroscopy. Antiproliferative activity was determined in a panel of human tumor cell Lines (CCRF-CEM, Burkitt's lymphoma, HeLa, ZR-75-1, HT-29, and MEXF 276L) in vitro. Generally, the new compounds were found to be more patent (IC(50) = 0.011-0.436 mu M) than the ribonucleotide reductase inhibitor hydroxyurea (IC(50) = 140 mu M) Most of the compounds exhibited the highest activity against Burkitt's lymphoma with an IC(50) Of 0.011-0.035 mu M. [(14)C]Cytidine incorporation into DNA was quantitated for selected hydrazones (Z-A, E-1, Z-3, Z-4, E-5, Z-5, E-13, E-18, Z-19, Z-24, and E-26) as a measure of the inhibition of-ribonucleotide reductase in Burkitt's lymphoma cells. The E-configurated compounds were found to inhibit [(14)C]cytidine incorporation to a greater extent (IC(50) = 0.67-5.05 mu M) than the Z-isomers (IC(50) = 7.20 to > 10 mu M). Principal component analysis of the IC(50) values obtained for inhibition of cell proliferation revealed that the cell lines tested can be grouped into three main families showing different sensitivities toward the compounds in our series [(i) CCRF-CEM, Burkitt's lymphoma, and Hela; (ii) HT-29; and (iii) MEXF 276 L].

  DOI：

  10.1021/jm970255w
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 吡啶 、 ferrous(II) sulfate heptahydrate 、 selenium(IV) oxide 、 ammonium peroxydisulfate 、 甲酸 、 二甲基亚砜 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (4-methoxyphenyl)(pyrazin-2-yl)methanone
  参考文献：
  名称：

  铁催化α-酮酸使N-杂芳烃微缩酰化

  摘要：

  已经开发出一种有效且温和的方案，用于含氮杂芳烃与α-酮酸的Minisci酰化反应。与常规的Minisci酰化条件不同，该化学过程是使用非贵金属Fe（II）代替昂贵的Ag（I）盐作为催化剂进行的。各种底物，包括脂族或芳族α-酮酸，以及各种N-杂芳烃，都证明与该方案兼容。放大实验也证明了该方法的实用性。

  DOI：

  10.1016/j.tet.2019.01.060

文献信息

• A New, Convenient Synthesis of Monoaroylpyrazines via Homolytic Substitution
  作者：G. Heinisch、G. Lötsch

  DOI：10.1055/s-1988-27484

  日期：——

  Reactions of 2-pyrazinecarboxylic acid (1) with aroyl radicals to give 5-aroyl-2-pyrazinecarboxylic acids 3 followed by decarboxylation provide convenient access to aryl 2-pyrazinyl ketones (2-aroylpyrazines) 4.

  2-吡嗪羧酸（1）与芳酰基反应生成 5-芳酰基-2-吡嗪羧酸 3，然后进行脱羧反应，可方便地获得芳基 2-吡嗪酮（2-芳酰基吡嗪）4。
• Divergent Acyl and Decarbonylative Liebeskind–Srogl Cross-Coupling of Thioesters by Cu-Cofactor and Pd–NHC (NHC = N-Heterocyclic Carbene) Catalysis
  作者：Shiyi Yang、Xiang Yu、Michal Szostak

  DOI：10.1021/acscatal.2c05550

  日期：2023.2.3

  cross-coupling reactions of thioesters by selective acyl C(O)–S cleavage have emerged as a powerful platform for the preparation of complex molecules. Herein, we report divergent Liebeskind–Srogl cross-coupling of thioesters by Pd–NHC (NHC = N-heterocyclic carbene) catalysis. The reaction provides straightforward access to functionalized ketones by highly selective C(acyl)–S cleavage under mild conditions. Most

  通过选择性酰基 C(O)-S 裂解进行的过渡金属催化硫酯交叉偶联反应已成为制备复杂分子的强大平台。在此，我们报道了 Pd-NHC（NHC = N-杂环卡宾）催化下硫酯的不同 Liebeskind-Srogl 交叉偶联。该反应通过在温和条件下高度选择性的 C(酰基)-S 裂解提供直接获得功能化酮的途径。最重要的是，这些条件使得一系列用敏感官能团修饰的复杂药物能够直接功能化，为药物化学项目提供有吸引力的产品。此外，还报道了通过 C(酰基)-S/C(芳基)-C(O) 裂解进行的脱羰 Liebeskind-Srogl 交叉偶联。 Cu金属辅助因子将反应途径引导至酰基或脱羰基途径。这种反应适用于复杂的药物。该反应代表了迄今为止发现的最温和的铃木交叉偶联脱羰反应。铜引导的发散酰基和硫酯的脱羰交叉偶联在复杂分子合成中开辟了化学空间。
• Production of monoacylpyrazines
  申请人：PHILIP MORRIS INCORPORATED

  公开号：EP0076085A1

  公开（公告）日：1983-04-06

  This invention provides a process for preparing monoacylpyrazines which involves coreacting an aldehyde (R-CHO) and a pyrazine compound corresponding to the formula: where R1, R2 and R3 are substituents selected from hydrogen and alkyl groups, and R1 and R when taken together with connecting elements may form an alicyclic or aromatic structure, and R in the aldehyde compound is selected from aliphatic, alicyclic and aromatic groups under free radical conditions in a heterogeneous reaction medium consisting of an organic phase and an aqueous phase. The compounds prepared have the formula: where R, R', R2 and R3 are as previously defined, which is then recovered.

  本发明提供了一种制备单酰基吡嗪的工艺，该工艺包括在由有机相和水相组成的异相反应介质中，在自由基条件下，将醛（R-CHO）和式中所对应的吡嗪化合物进行共反应： 式中 R1、R2 和 R3 是选自氢和烷基的取代基，R1 和 R 与连接元素结合在一起时可形成脂环族或芳香族结构，醛化合物中的 R 选自脂肪族、脂环族和芳香族基团。 所制备的化合物具有式： 式中 R、R'、R2 和 R3 如前定义，然后将其回收。
• Houminer, Y.; Southwick, E. W.; Williams, D. L., Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 497 - 500
  作者：Houminer, Y.、Southwick, E. W.、Williams, D. L.

  DOI：——

  日期：——
• SCHWAIGER, W.;CORNELISSEN, J. M.;WARD, J. P., FOOD CHEM., 1984, 13, N 3, 225-234
  作者：SCHWAIGER, W.、CORNELISSEN, J. M.、WARD, J. P.

  DOI：——

  日期：——