2-phenethyl-1-phenyl-2,3-dihydropyridin-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-phenethyl-1-phenyl-2,3-dihydropyridin-4(1H)-one
• 英文别名: 1-Phenyl-2-(2-phenylethyl)-2,3-dihydropyridin-4-one
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: NXURGABKQLHCQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯丙醛 、 反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 苯胺 在 sodium 2,2,2-trifluoroacetate 作用下， 以70%的产率得到2-phenethyl-1-phenyl-2,3-dihydropyridin-4(1H)-one
  参考文献：
  名称：

  Danishefsky的二烯与亚胺在碱性条件下的碱性盐催化氮杂Diels-Alder反应。

  摘要：

  Danishefsky's二烯与亚胺或醛和胺在水中的两或三组分氮杂Diels-Alder反应在中性条件下在催化量的碱性盐（例如三氟甲磺酸钠）存在下平稳进行，得到二氢-4-吡啶酮高产。

  DOI：

  10.1039/b300880k

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。
• Alkaline salt-catalyzed aza Diels–Alder reactions of Danishefsky’s diene with imines in water under neutral conditions
  作者：Catherine Loncaric、Kei Manabe、Shū Kobayashi

  DOI：10.1039/b300880k

  日期：2003.2.20

  Two- or three-component aza Diels-Alder reactions of Danishefsky's diene with imines or aldehydes and amines in water took place smoothly under neutral conditions in the presence of a catalytic amount of an alkaline salt such as sodium triflate to afford dihydro-4-pyridones in high yields.

  Danishefsky's二烯与亚胺或醛和胺在水中的两或三组分氮杂Diels-Alder反应在中性条件下在催化量的碱性盐（例如三氟甲磺酸钠）存在下平稳进行，得到二氢-4-吡啶酮高产。
• 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。
• AgOTf-Catalyzed Aza-Diels–Alder Reactions of Danishefsky's Diene with Imines in Water
  作者：Catherine Loncaric、Kei Manabe、Shū Kobayashi

  DOI：10.1002/adsc.200390052

  日期：2003.4

  Aza-Diels–Alder reactions of Danishefsky's diene with imines in water took place smoothly in the presence of a catalytic amount of silver triflate to afford dihydro-4-pyridones in high yields. The silver triflate-catalyzed three-component reactions starting from aldehydes, amines, and Danishefsky's diene were also performed efficiently. In the three-component reactions with benzaldehyde, the addition

  在催化量的三氟甲磺酸银存在下，Danishefsky的二烯与亚胺在水中的Aza-Diels-Alder反应平稳进行，从而以高收率提供二氢-4-吡啶酮。从醛，胺和Danishefsky的二烯开始的三氟甲磺酸银催化的三组分反应也得到了有效地进行。在与苯甲醛的三组分反应中，发现添加非离子表面活性剂是有效的。
• Wu, Liqiang; Yang, Limin; Yan, Fulin, Asian Journal of Chemistry, 2010, vol. 22, # 9, p. 6977 - 6982
  作者：Wu, Liqiang、Yang, Limin、Yan, Fulin

  DOI：——

  日期：——