(E)-1-methyl-3-styrylquinolin-4(1H)-one | 1227000-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (E)-1-methyl-3-styrylquinolin-4(1H)-one
• 英文别名: 1-methyl-3-[(E)-2-phenylethenyl]quinolin-4-one
• CAS: 1227000-53-4
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: QSNYNQZPTZJVPC-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-methyl-3-styrylquinolin-4(1H)-one 以 乙醇 、 水 为溶剂， 反应 4.5h， 以80%的产率得到(2-(methylamino)phenyl)(naphthalen-2-yl)methanone
  参考文献：
  名称：

  在 365 nm 紫外光照射下通过 (E)-3-苯乙烯基喹啉-4(1H)-酮的分子内重排合成 (2-氨基苯基)(萘-2-基)甲酮

  摘要：

  开发了一种高效环保的（2-氨基苯基）（萘-2-基）甲酮合成方法。(E)-3-苯乙烯基喹啉-4(1H)-酮在 EtOH-H 2 中的辐照以高产率（高达 96%）获得（2-氨基苯基）（萘-2-基）甲酮衍生物O (7:1) 与紫外光 (365 nm) 在室温下在 Ar 气氛下。所证明的光诱导分子内重排与其他过渡金属催化反应相比具有优势，例如不需要添加剂、绿色溶剂、底物范围广和原子效率高。

  DOI：

  10.1055/s-0037-1610176
• 作为产物：
  描述：

  4-羟基喹啉 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 碘 、 palladium diacetate 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 14.0h， 生成 (E)-1-methyl-3-styrylquinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis, antibacterial evaluation, and docking studies of azaisoflavone analogues generated by palladium-catalyzed cross coupling

  摘要：

  Palladium-catalyzed, cross-coupling reaction of N-methyl-3-iodo-4-quinolone with boronic acids or N-methyliminodi-acetic acid boronates to obtain azaisoflavone derivatives was investigated through conventional Suzuki Miyuara coupling or by slow release strategy. It has been observed that a slow release approach was a highly successful. In addition, a series of novel azaisoflavones containing alkynyl group were synthesized via Sonogashira reaction. The antibacterial activities of the all synthesized compounds were screened against series of bacterial strains. Furthermore, a molecular docking study was carried out for the most active compounds using Leadit 2.1.8 docking software, and the results were in good agreement with the experimental data. The details of synthetic methods, spectroscopic data, and biological results are reported.[GRAPHICS]

  DOI：

  10.1007/s00706-018-2252-5

文献信息

• Synthesis of (E)-3-Styrylquinolin-4(1H)-ones in Water by Ohmic Heating: a Comparison with Other Methodologies
  作者：Joana Pinto、Vera L. M. Silva、Luis M. N. B. F. Santos、Artur M. S. Silva

  DOI：10.1002/ejoc.201600150

  日期：2016.6

  Ohmic heating offers a very efficient way to perform organic reactions in aqueous media. Potentially bioactive (E)-3-styrylquinolin-4(1H)-ones were synthesized by the Heck reaction of 3-iodo-1-methylquinolin-4(1H)-one with styrenes in water and with ohmic heating. Pd(OAc)2 was used as catalyst, and tetrabutylammonium bromide was used as phase-transfer catalyst in the presence of an inorganic base.

  欧姆加热提供了一种在水性介质中进行有机反应的非常有效的方法。具有潜在生物活性的 (E)-3-styrylquinolin-4(1H)-ones 是通过 3-iodo-1-methylquinolin-4(1H)-one 与苯乙烯在水中和欧姆加热的 Heck 反应合成的。Pd(OAc)2用作催化剂，四丁基溴化铵用作在无机碱存在下的相转移催化剂。与其他既定程序的比较突出了这种新方法的好处。
• Reactivity of 3-Iodo-4-quinolones in Heck Reactions: Synthesis of Novel (E)-3-Styryl-4-quinolones
  作者：Artur Silva、Andreia Almeida、José Cavaleiro

  DOI：10.1055/s-0029-1219175

  日期：2010.2

  A new and efficient route for the synthesis of (E)-N-­methyl-3-styryl-4-quinolones is described. It involves the Heck ­reaction of N-methyl-3-iodo-4-quinolone, which is obtained by consecutive 3-iodination and NH-methylation of the unsubstituted 4-quinolone, with styrene derivatives. It is demonstrated that such a procedure is only efficient when the 3-iodo-4-quinolone has an N-protecting group. In some cases the branched regioisomers N-methyl-3-(1-phenylethenyl)-4-quinolones were also obtained as byproducts.

  描述了一种新颖且高效的合成（E)-N-甲基-3-苯乙烯基-4-喹啉酮的路线。该方法涉及将N-甲基-3-碘-4-喹啉与苯乙烯衍生物进行Heck反应，而N-甲基-3-碘-4-喹啉是通过对未取代的4-喹啉进行连续的3-碘化和NH-甲基化获得的。研究表明，只有在3-碘-4-喹啉具有N-保护基团时，该程序才有效。在某些情况下，支链 regioisomers N-甲基-3-(1-苯乙烯基)-4-喹啉酮也作为副产物获得。
• New Synthesis of (Z)- and (E)-3-Styryl-4-quinolones
  作者：Artur Silva、Raquel Seixas、José Cavaleiro

  DOI：10.1055/s-0030-1258042

  日期：2010.9

  efficient route for the synthesis of (Z)- and (E)-3-styryl-4-quinolones is described. Wittig reaction of 4-(chlo- roquinoline- and quinolone)-3-carbaldehydes with benzylic ylides is the key transformation for this synthetic route. The (Z)-1-methyl- 3-styryl-4-quinolone is obtained with high diastereoselectivity from the reaction of 1-methyl-4-quinolone-3-carbaldehyde; while (E)-3- styryl-4-quinolone

  描述了一种合成 (Z)- 和 (E)-3-styyl-4-quinolones 的新型有效途径。4-（氯喹啉和喹诺酮）-3-甲醛与苄基叶立德的 Wittig 反应是该合成路线的关键转变。(Z)-1-甲基-3-苯乙烯基-4-喹诺酮是由1-甲基-4-喹诺酮-3-甲醛反应以高非对映选择性得到的；而(E)-3-苯乙烯基-4-喹诺酮是通过4-氯喹啉-3-甲醛的Wittig反应然后酸水解制备的。无论苄基叶立德上的取代基如何，这两种合成路线都是有效的。
• An experimental NMR and computational study of 4-quinolones and related compounds
  作者：Raquel S. G. R. Seixas、Artur M. S. Silva、Ibon Alkorta、José Elguero

  DOI：10.1007/s00706-011-0473-y

  日期：2011.7

  AbstractWe report the synthesis and structural study of eight compounds, either quinolin-4(1H)-ones or quinolines. Tautomerism as well as (E) → (Z) and rotational isomerism were studied both experimentally (1H and 13C NMR) and theoretically [B3LYP/6-311++G(d,p)]. Graphical Abstract

  摘要我们报告了八个化合物，喹啉4（1 H）一或喹啉的合成和结构研究。通过实验（1 H和13 C NMR）和理论上[B3LYP / 6-311 ++ G（d，p）]研究互变异构以及（E）→（Z）和旋转异构现象。 图形概要