(RS)-1-methyl-2-phenyl-2,3-dihydro-1H-pyridin-4-one | 653579-37-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (RS)-1-methyl-2-phenyl-2,3-dihydro-1H-pyridin-4-one
• 英文别名: 1-methyl-2-phenyl-2,3-dihydro-1H-pyridin-4-one；1-methyl-2-phenyl-2,3-dihydropyridin-4(1H)-one；4(1H)-Pyridinone, 2,3-dihydro-1-methyl-2-phenyl-；1-methyl-2-phenyl-2,3-dihydropyridin-4-one
• CAS: 653579-37-4
• 化学式: C₁₂H₁₃NO
• mdl: MFCD09033584
• 分子量: 187.241
• InChiKey: ABAOSSLZYLOOKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (RS)-1-methyl-2-phenyl-2,3-dihydro-1H-pyridin-4-one 在 sodium periodate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 87.0h， 以83%的产率得到(RS)-3-methylamino-3-phenylpropionic acid hydrochloride
  参考文献：
  名称：

  Synthesis of β-Amino Acids Based on Oxidative Cleavage of Dihydropyridone Derivatives

  摘要：

  A new method for the synthesis of beta-amino acids based on 2,3-dihydropyridones as starting materials is presented. Conversions of 2,3-dihydropyridones with NalO(4) and subsequently with base gave the corresponding beta-amino acids in a one-pot procedure. The reactions have been monitored by H-1 NMR indicating that the beta-amino acids were formed in quantitative yields mostly. This method appears to be of broad scope, as 2-substituted 2,3-dihydropyridones are easily accessible via N-acyliminium ions generated from 4-methoxypyridine.

  DOI：

  10.1021/ol0485518
• 作为产物：
  描述：

  4-甲氧基吡啶 在 sodium methylate 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.5h， 生成 (RS)-1-methyl-2-phenyl-2,3-dihydro-1H-pyridin-4-one
  参考文献：
  名称：

  Synthesis of β-Amino Acids Based on Oxidative Cleavage of Dihydropyridone Derivatives

  摘要：

  A new method for the synthesis of beta-amino acids based on 2,3-dihydropyridones as starting materials is presented. Conversions of 2,3-dihydropyridones with NalO(4) and subsequently with base gave the corresponding beta-amino acids in a one-pot procedure. The reactions have been monitored by H-1 NMR indicating that the beta-amino acids were formed in quantitative yields mostly. This method appears to be of broad scope, as 2-substituted 2,3-dihydropyridones are easily accessible via N-acyliminium ions generated from 4-methoxypyridine.

  DOI：

  10.1021/ol0485518

文献信息

• 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。
• Iridium-Catalyzed Reductive Alkylations of Secondary Amides
  作者：Wei Ou、Feng Han、Xiu-Ning Hu、Hang Chen、Pei-Qiang Huang

  DOI：10.1002/anie.201806747

  日期：2018.8.27

  Reported herein is the first direct, metal‐catalyzed reductive functionalization of secondary amides to give functionalized amines and heterocycles. The method is shown to have exceptionally broad scope with respect to suitable nucleophiles, which cover both hard and soft C nucleophiles as well as a P nucleophile. The reaction exhibits good chemoselectivity and tolerates several sensitive functional

  本文报道的是仲酰胺的第一个直接的，金属催化的还原性官能化反应，以生成官能化的胺和杂环。相对于合适的亲核试剂，该方法具有广泛的适用范围，既涵盖硬C亲核试剂，也包括软C亲核试剂和P亲核试剂。该反应表现出良好的化学选择性，并能耐受几个敏感的官能团。
• Diastereoselective synthesis of β-amino acid derivatives from dihydropyridones
  作者：Markus Ege、Klaus T. Wanner

  DOI：10.1016/j.tet.2008.05.073

  日期：2008.7

  A new method for the diastereoselective preparation of stereoisomeric 2,3-disubstituted β-amino acids is presented. It is based on trans- and cis-2,3-disubstituted dihydropyridones, which were derived from 2-monosubstituted N-acyl dihydropyridone derivatives. Alkylation of the enolates of 2-substituted dihydropyridones gave trans-2,3-disubstituted dihydropyridones with high diastereoselectivities.

  提出了一种非对映选择性制备立体异构体2,3-二取代的β-氨基酸的新方法。它是基于反式-和顺-2,3-二取代的二氢吡啶，将其衍生自2单取代Ñ酰基二氢吡啶酮衍生物。2-取代的二氢吡啶酮的烯醇盐的烷基化得到具有高非对映选择性的反式-2,3-二取代的二氢吡啶酮。通过去质子化/再质子化序列使二氢吡啶酮核的C-3处的立体中心反转，从而以高收率和非对映选择性产生了立体异构体顺式-2,3-二取代的二氢吡啶酮。除去N之后-酰基保护基团，高碘酸钠分别氧化生成的顺式或反式-2,3-异位二氢吡啶酮，导致相应的非对映体β-氨基酸氧化降解。
• Domino Palladium(II)-Mediated Rearrangement-Oxidative Cyclization of β-Aminocyclopropanols
  作者：Alberto Brandi、Stefano Cicchi、Julia Revuelta、Alessandra Zanobini、Matteo Betti

  DOI：10.1055/s-2003-42122

  日期：——

  β-Aminocyclopropanols were transformed, in a domino process catalyzed by Pd(II) salts, into the corresponding 2,3-dihydro-1H-pyridin-4-ones. Conversely the use of a Pd(0) derivative, Pd(dba)2, afforded the corresponding tetrahydropyrid-4-ones. The saturated derivatives were also obtained, in better yields, using Pd(II) and Cu(OAc)2 as stoichiometric oxidant.

  在由Pd(II)盐催化的多米诺反应中，β-氨基环丙醇被转化为相应的2,3-二氢-1H-吡啶-4-酮。相反，使用Pd(0)衍生物Pd(dba)2则可得到相应的四氢吡啶-4-酮。使用Pd(II)和Cu(OAc)2作为化学计量氧化剂，也能得到饱和衍生物，且产率更高。
• 2-Halogenoimidazolium Salt Catalyzed Aza-Diels–Alder Reaction through Halogen-Bond Formation
  作者：Youhei Takeda、Daichi Hisakuni、Chun-Hsuan Lin、Satoshi Minakata

  DOI：10.1021/ol503426f

  日期：2015.1.16

  2-Halogenoimidazolium salts are found to catalyze aza-Diels-Alder reaction of aldimines with Danishefsky diene in an efficient manner. Comparative studies and titration experiments support the formation of halogen bonding between imines and catalysts.