4-Methyl-1-phenyl-6-(2-pyridyl)-5,6-dihydropyridin-2-one | 110362-28-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-Methyl-1-phenyl-6-(2-pyridyl)-5,6-dihydropyridin-2-one
• 英文别名: 4-methyl-1,6-diphenyl-5,6-dihydropyridin-2(1H)-one；4-Methyl-1,2-diphenyl-2,3-dihydropyridin-6-one
• CAS: 110362-28-2
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: GWEMHJVGHKKLNA-UHFFFAOYSA-N

物化性质

• 沸点：
  384.0±42.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N,3-dimethyl-N-(methylsulfonyl)-N',5-diphenyl-5-(phenylamino)pent-2-enimidamide 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 4-Methyl-1-phenyl-6-(2-pyridyl)-5,6-dihydropyridin-2-one
  参考文献：
  名称：

  3-En-1-酰胺与苯胺和醛的金催化的亚胺/曼尼希反应级联反应，可实现1,5-氮功能化

  摘要：

  金催化的亚胺/曼尼希反应在易于使用的3烯1酰胺上进行级联，可在一锅操作中非对映选择性地合成1,5-亚氨基氨基化合物。该反应可与具有良好或优异的非对映选择性的多样化3-1-1-酰胺，醛和苯胺一起使用。我们的对照实验表明，金催化的3-en-1-酰胺的胺化反应可生成α-亚氨基烯丙基金的中间体，这些中间体随后可与亚胺反应，选择性地实现曼尼希反应。该反应继续进行抗那些-3-烯-1- ynamides轴承无环烯烃，而-选择性顺他们的基于环烯烃的类似物具有选择性。开放过渡态可以基于反平面构象令人满意地合理化这些观察到的立体选择性。

  DOI：

  10.1002/adsc.201600072

文献信息

• Reactions of ketene silyl acetals with imine-complexes of titanium tetrachloride. New and convenient routes to 5,6-dihydro-2-pyridones and 5-amino-2-alkenoates
  作者：Stephan M. Brandstadter、Iwao Ojima、Kenji Herai

  DOI：10.1016/s0040-4039(00)95794-0

  日期：1987.1

  The reactions of vinylketene silyl acetals (VKSAs) with imine complexes of TiCl4 give the corresponding 5,6-dihydro-2-pyridones and/or 5-amino-2-alkenoates in good to excellent yields. It is suggested that an addition-cyclization mechanism is operative for the formation of 5,6-dihydro-2-pyridones in this formal cyclocondensation reaction.

  乙烯基乙烯酮甲硅烷基乙缩醛（VKSAs）与TiCl 4的亚胺配合物的反应可产生相应的5,6-二氢-2-吡啶酮和/或5-氨基-2-链烯酸酯，且收率高至优异。建议在该正式的环缩合反应中，加成环化机理可用于形成5，6-二氢-2-吡啶酮。
• Dualistic Reactivity of Lithium and Zinc Dienolates with Imines: Effects of Counterion, Temperature, and Substituents on .alpha.- and .gamma.-Coupling
  作者：Hendrik L. van Maanen、Henk Kleijn、Johann T. B. H. Jastrzebski、Miles T. Lakin、Anthony L. Spek、Gerard van Koten

  DOI：10.1021/jo00104a048

  日期：1994.12

  Lithium and zinc dienolates of 3-butenoic, 3-methyl-2-butenoic, 3-pentenoic, and 4-phenyl-3-butenoic methyl esters are reacted with imines R(1)C(H)=NR(2)[3a: R(1) = 2-pyridyl, R(2) = Ph; 3b: R(1) = Me(3)-SiC=C; R(2) = Ph; 3c: R(1) = 2-pyridyl, R(2) = (R)-PhCK(CH3); 3d: R(1) = Me(3)SiC=C; R(2) = (R)-PhCH(CH3)]. Depending on metal counterion, temperature, and substituents, the C-C coupling occurs either at the 2-position (alpha-coupling) or at the C-position (gamma-coupling) of the dienolate, giving beta-amino esters and alpha,beta-unsaturated esters, respectively. The alpha-coupling occurs at -78 degrees C and is reversible, whereas gamma-coupling products are formed upon warming to -20 degrees C. The C-C coupled products may undergo irreversible ring closure to beta-lactams (from beta-amino esters) or 5,6-dihydropyridin-2-ones (from Z)-alpha,beta-unsaturated esters). Starting from enantiomerically pure imine 3c, high (71-92%) asymmetric inductions were realized in both beta-lactams and 5,6-dihydropyridin-2-ones; gamma-coupling of enolate 2a and chiral imine 3d occurred with low diastereoselectivity (15%). Four factors favor the formation of beta-lactams: (i) the use of zinc dienolates, (ii) 4-substitution of the dienolates, (iii) nonaromatic imine N-substituents, and (iv) a low reaction temperature (-78 degrees C). The product formation is discussed in terms of six-membered cyclic transition states, involving either zinc enolates (alpha-coupling) or isomeric allylzinc species (gamma-coupling).
• BRANDSTADTER S. M.; OJIMA IWAO, TETRAHEDRON LETT., 28,(1987) N 6, 613-616
  作者：BRANDSTADTER S. M.、 OJIMA IWAO

  DOI：——

  日期：——