2-(furan-2-yl)-2,3-dihydro-1-phenylpyridin-4(1H)-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(furan-2-yl)-2,3-dihydro-1-phenylpyridin-4(1H)-one
• 英文别名: 2-(Furan-2-yl)-1-phenyl-2,3-dihydropyridin-4-one
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: AKUNTFUIBQNUII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(2-furylmethylene)aniline 、 1-甲氧基-3-三甲基硅氧基-1,3-丁二烯 在 1,1-dimethylpiperidinium tetra(3,5-di(trifluoromethyl)phenyl)borate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以46%的产率得到2-(furan-2-yl)-2,3-dihydro-1-phenylpyridin-4(1H)-one
  参考文献：
  名称：

  Aza-Diels-Alder反应中四烷基铵盐的氢键催化

  摘要：

  哌啶衍生的四烷基铵盐与非配位抗衡阴离子在亚胺和Danishefsky二烯的aza-Diels-Alder反应中作为有效的氢键催化剂。在1 H NMR滴定研究中，观察到了铵盐和亚胺之间的氢键相互作用。

  DOI：

  10.1002/asia.201600781

文献信息

• Brønsted acid-catalyzed aza Diels-Alder reaction of Danishefsky's diene with aldimine generated in situ from aldehyde and amine in aqueous media
  作者：Takahiko Akiyama、Jun Takaya、Hirotaka Kagoshima

  DOI：10.1016/s0040-4039(99)01630-5

  日期：1999.10

  Three-component aza Diels-Alder reaction, starting from aldehyde, aniline, and Danishefsky's diene, took place smoothly under the influence of HBF4 in aqueous media to afford dihydro-4-pyridone derivatives in high yields.

  由醛，苯胺和Danishefsky的二烯开始的三组分氮杂Diels-Alder反应在HBF 4的影响下在水性介质中顺利进行，从而以高收率得到二氢-4-吡啶酮衍生物。
• Trialkylsulfonium and Tetraalkylammonium Salts as Hydrogen-Bonding Catalysts in an Aza-Diels-Alder Reaction: Experimental and Computational Studies
  作者：Masahiro Yamanaka、Seiji Shirakawa、Ayaka Mochizuki、Takumi Nakamura、Keiji Maruoka

  DOI：10.3987/com-19-s(f)48

  日期：——

  cyclic trialkylsulfonium and tetraalkylammonium salts in an aza-Diels-Alder reaction was investigated. Among the examined onium salt catalysts, cyclic trialkylsulfonium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate possessing a non-coordinating counter anion was the most effective. Details of the activation modes of cyclic trialkylsulfonium and tetraalkylammonium salts were discussed on the basis of

  研究了环三烷基锍和四烷基铵盐在氮杂-狄尔斯-阿尔德反应中的氢键催化作用。在所检查的鎓盐催化剂中，具有非配位抗衡阴离子的环状三烷基锍四[3,5-双(三氟甲基)苯基]硼酸盐是最有效的。详细讨论了环状三烷基锍和四烷基铵盐的活化模式
• A New Approach to Di- and Tetrasubstituted 2,3-Dihydropyridin-4(1H)-ones through Aza-Diels-Alder Reaction Promoted by Silicon Tetrachloride
  作者：Antonio Massa、Vincenzo de Sio、Rosaria Villano、M. Acocella、Laura Palombi、Giusi Sellitto、Antonella Peduto、Rosanna Filosa、Paolo De Capraris、Arrigo Scettri

  DOI：10.1055/s-0028-1087677

  日期：2009.2

  Silicon tetrachloride promotes an aza-Diels-Alder reaction with a range of imines and Danishefsky’s diene or an alkylated derivative, giving the desired products in good to excellent yields. aza-Diels-Alder reaction - heterocycles - silicon tetrachloride

  四氯化硅可促进与一系列亚胺和Danishefsky的二烯或烷基化衍生物的aza-Diels-Alder反应，以高至极好的收率获得所需的产物。 氮杂-狄尔斯-阿尔德反应-杂环-四氯化硅
• Acid-Free Aza Diels−Alder Reaction of Danishefsky's Diene with Imines
  作者：Yu Yuan、Xin Li、Kuiling Ding

  DOI：10.1021/ol0265822

  日期：2002.9.1

  [reaction: see text] A highly efficient aza Diels-Alder reaction of Danishefsky's diene with imines was found to occur in methanol in the absence of any acids at room temperature to give corresponding 2-substituted dihydro-4-pyridone derivatives in high yields. This reaction can be also carried out in a three-component one-pot reaction manner. The reaction was found to proceed through a Mannich-type

  [反应：见正文]在室温下，在无酸的情况下，甲醇中发生Danishefsky's二烯与亚胺的高效氮杂Diels-Alder反应，以高收率得到相应的2-取代的二氢-4-吡啶酮衍生物。该反应也可以以三组分一锅法进行。发现该反应通过曼尼希型缩合机理进行。
• Sustainable Synthetic Methods: Domino Construction of Dihydropyridin-4-ones and β-Amino Esters in Aqueous Ethanol
  作者：Peter J. Alaimo、Robert O’Brien、Adam W. Johnson、Sarah R. Slauson、Jeannette M. O’Brien、Elizabeth L. Tyson、Amanda-Lynn Marshall、Colleen E. Ottinger、Jon G. Chacon、Lorien Wallace、Corey Y. Paulino、Sarah Connell

  DOI：10.1021/ol801911f

  日期：2008.11.20

  Domino reactions were designed to allow the byproduct of an upstream reaction to be internally recycled to catalyze a downstream reaction in a one-pot tandem sequence. Nitroarene reduction by In(0) generates an amine and In(III) byproducts. Addition of aldehyde followed by Danishefsky's diene or silyl ketene acetal provides access to dihydropyridin-4-ones or,beta-amino esters, respectively, in yields that are comparable or superior to the reported stepwise reactions.