2,3-dihydro-2-(4-chlorophenyl)-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: 2,3-dihydro-2-(4-chlorophenyl)-1-phenylpyridin-4(1H)-one
• 英文别名: N-phenyl-2,3-dihydro-2-(4-chlorophenyl)-4-pyridone；2-(4-chlorophenyl)-1-phenyl-2,3-dihydro-1H-pyridin-4-one；2-(4-chlorophenyl)-1-phenyl-2,3-dihydropyridin-4(1H)-one；2-(4-Chlorophenyl)-1-phenyl-2,3-dihydropyridin-4-one
• 化学式: C₁₇H₁₄ClNO
• 分子量: 283.757
• InChiKey: QFJLRPUFFNGXOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 (E)-1-(4-chlorophenyl)-N-phenylmethanimine 在 1,3-dibenzyl-2-(pentafluorophenyl)imidazolinium hexafluorophosphate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以72%的产率得到2,3-dihydro-2-(4-chlorophenyl)-1-phenylpyridin-4(1H)-one
  参考文献：
  名称：

  Imidazolinium salts as catalysts for the aza-Diels–Alder reaction

  摘要：

  已发现多种易于获得的咪唑鎓盐能够催化具有一系列亚胺和丹尼谢夫斯基二烯的aza-Diels-Alder反应，得到良好至极好产率的目标产物。探讨了对阴离子对反应性的影响。这些盐可能有助于无金属催化/有机催化领域的发展。

  DOI：

  10.1039/b415023f

文献信息

• Aza-Diels–Alder reaction catalyzed by perfluorinated metal salts in fluorous phase
  作者：Min Shi、Shi-Cong Cui

  DOI：10.1039/b406878e

  日期：——

  In this paper, we describe the aza-Diels–Alder reaction of Danishefsky’s diene with arylaldehydes and aromatic amines in a fluorous phase. With perfluorodecalin (C10F18, cis- and trans-mixture) as the fluorous solvent and a perfluorinated rare earth metal salt [Sc(OSO2C8F17)3] (2.0 mol %) as a catalyst, this aza-Diels–Alder reaction can be performed many times without reloading the catalyst.

  在本文中，我们描述了丹尼谢夫斯基二烯与芳香醛和芳香胺在氟相中进行的氮杂Diels-Alder反应。以全氟去卡林（C10F18，顺式和反式混合物）作为氟溶剂，以全氟稀土金属盐[Sc(OSO2C8F17)3]（2.0 mol%）作为催化剂，这个氮杂Diels-Alder反应可以多次进行而无需重新装载催化剂。
• 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。
• Aza Diels–Alder reactions utilizing 4-iodo-2-trimethylsilyloxy-butadiene
  作者：Cody Timmons、Adiseshu Kattuboina、Lauren McPherson、James Mills、Guigen Li

  DOI：10.1016/j.tet.2005.10.018

  日期：2005.12

  The aza Diels-Alder reaction is described for a novel diene. Imines bearing benzyl and aromatic protecting groups both work well. Moderate diastereoselectivities can be obtained using the simple alpha-methylbenzyl chiral auxiliary. (c) 2005 Elsevier Ltd. All rights reserved.
• 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：——