1-(4-methoxyphenyl)-2-phenyl-2,3-dihydropyridin-4(1H)-one | 168326-39-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxyphenyl)-2-phenyl-2,3-dihydropyridin-4(1H)-one
• 英文别名: 1-(4-methoxy-phenyl)-2-phenyl-2,3-dihydro-1H-pyridin-4-one；4(1H)-Pyridinone, 2,3-dihydro-1-(4-methoxyphenyl)-2-phenyl-；1-(4-methoxyphenyl)-2-phenyl-2,3-dihydropyridin-4-one
• CAS: 168326-39-4
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: XEFIKKIXPKUYLS-UHFFFAOYSA-N

物化性质

• 熔点：
  111 °C
• 沸点：
  451.5±45.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基-N-[(1Z)-苯基亚甲基]苯胺 在 bismuth(III) chloride 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1-(4-methoxyphenyl)-2-phenyl-2,3-dihydropyridin-4(1H)-one
  参考文献：
  名称：

  Laurent-Robert; Garrigues; Dubac, Synlett, 2000, # 8, p. 1160 - 1162

  摘要：

  DOI：

文献信息

• Imino-Diels–Alder and imino-aldol reactions catalyzed by samarium diiodide
  作者：Jacqueline Collin、Nada Jaber、Marie Isabelle Lannou

  DOI：10.1016/s0040-4039(01)01581-7

  日期：2001.10

  In the presence of a catalytic amount of samarium diiodide in methylene chloride, aromatic imines react with Danishefsky diene to form tetrahydropyridine-4-ones in high yields. Under the same conditions, various imino-aldol reactions afford β-amino esters or β-amino ketones.

  在二氯甲烷中催化量的二碘化sa存在下，芳族亚胺与Danishefsky二烯反应形成高产率的四氢吡啶-4-酮。在相同条件下，各种亚氨基-羟醛反应可得到β-氨基酯或β-氨基酮。
• A simple ketone as an efficient metal-free catalyst for visible-light-mediated Diels–Alder and aza-Diels–Alder reactions
  作者：Jiri Kollmann、Yu Zhang、Waldemar Schilling、Tong Zhang、Daniel Riemer、Shoubhik Das

  DOI：10.1039/c9gc00485h

  日期：——

  Diels–Alder reactions are highly effective between electron-rich dienes and electron-poor dienophiles. However, these reactions with electron-rich dienophiles are limited and require forcing conditions. Based on this, an efficient metal-free homogeneous system has been developed for the Diels–Alder reactions between electron-rich dienophiles and dienes under visible-light conditions. Additionally,

  Diels–Alder反应在富电子二烯和贫电子双亲物之间非常有效。然而，这些与富含电子的亲二烯体的反应是有限的，并且需要强制条件。基于此，已经开发出了一种有效的无金属均相系统，用于可见光条件下富电子的亲二烯体和二烯之间的狄尔斯-阿尔德反应。此外，该催化剂对aza-Diels-Alder反应显示出出色的反应活性。这种简单的催化剂是可商购的，无毒且便宜的，并且显示出优异的反应性，其与报道的基于金属的催化剂相当并且在某些情况下甚至更好。最后，基于实验证据提出了该反应的机理。
• Lanthanide Triflate Catalyzed Imino Diels-Alder Reactions; Convenient Syntheses of Pyridine and Quinoline Derivatives
  作者：Shū Kobayashi、Haruro Ishitani、Satoshi Nagayama

  DOI：10.1055/s-1995-4066

  日期：1995.9

  Lanthanide triflate catalyzed imino Diels-Alder reactions of imines with dienes or alkenes have been developed. A new group of Lewis acids, lanthanide triflates, are quite effective for the catalytic activation of imines. Unique reactivities of imines which work as both dienophiles and azadienes under certain conditions have been revealed. Three-component coupling reactions between aldehydes, amines, and dienes or alkenes were successfully carried out by using lanthanide triflate as a catalyst to afford pyridine and quinoline derivatives in high yields. The Lewis acid catalysts were stable and kept their activity even in the presence of water and amines. A stepwise reaction mechanism for these reactions is suggested from the experimental results.

  已开发了铈三氟甲磺酸盐催化的亚胺与二烯或烯烃的亚胺Diels-Alder反应。新一类路易斯酸，即铈三氟甲磺酸盐，在催化亚胺的活化方面非常有效。已揭示出亚胺在某些条件下同时作为二烯亲和体和氮烯体的独特反应性。通过使用铈三氟甲磺酸盐作为催化剂，成功进行了醛、胺与二烯或烯烃之间的三组分偶联反应，得到高产率的吡啶和喹啉衍生物。这些路易斯酸催化剂在水和胺存在的情况下依然保持稳定性和活性。根据实验结果，提出了这些反应的逐步反应机理。
• Ln(OTf)₃- or Sc(OTf)₃-Catalyzed Three Components Coupling Reactions between Aldehydes, Amines, and Dienes or Alkenes. Efficient Syntheses of Pyridine and Quinoline Derivatives
  作者：Shu Kobayashi、Haruro Ishitani、Satoshi Nagayama

  DOI：10.1246/cl.1995.423

  日期：1995.6

  Three components coupling reactions between aldehydes, amines, and dienes or alkenes were catalyzed by lanthanide or scandium triflate to afford pyridine and quinoline derivatives in high yields. The Lewis acid catalysts were stable and kept their activity even in the presence of water and amines.

  在镧系元素或三氟甲磺酸钪的催化下，醛、胺和二烯或烯烃之间的三组分偶联反应以高产率得到吡啶和喹啉衍生物。即使在水和胺的存在下，路易斯酸催化剂也很稳定并保持其活性。
• Copper(II) Triflate-Sodium Dodecyl Sulfate Catalyzed Preparation of 1,2-Diphenyl-2,3-dihydro-4-pyridones in Aqueous Acidic Medium
  作者：Ferdinando Pizzo、Luigi Vaccaro、Daniela Lanari、Oriana Piermatti

  DOI：10.1055/s-0031-1291040

  日期：2012.7

  loss in efficiency. The reactions between N-benzylideneanilines and ­Danishefsky’s diene proceed smoothly in acidic aqueous medium in the presence of a catalytic amount of copper(II) triflate–sodium dodecyl sulfate [Cu(OTf)2–SDS] to afford the corresponding 1,2-diphenyl-2,3-dihydro-4-pyridones in excellent yields of 84–95%. The aqueous solution containing the catalyst is recovered and reused without any

  摘要 在催化量的三氟甲磺酸铜（II）-十二烷基硫酸钠[Cu（OTf）2 -SDS]存在下，N-苄叉基苯胺和Danishefsky's二烯之间的反应在酸性水性介质中平稳进行，得到相应的1,2-二苯基-2,3-二氢-4-吡啶酮类化合物的收率为84–95％。含有催化剂的水溶液被回收并再利用而效率没有任何损失。 在催化量的三氟甲磺酸铜（II）-十二烷基硫酸钠[Cu（OTf）2 -SDS]存在下，N-苄叉基苯胺和Danishefsky's二烯之间的反应在酸性水性介质中平稳进行，得到相应的1,2-二苯基-2,3-二氢-4-吡啶酮类化合物的收率为84–95％。含有催化剂的水溶液被回收并再利用而效率没有任何损失。