N-methyl-3-oxo-N,3-diphenylpropanamide | 2665-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-methyl-3-oxo-N,3-diphenylpropanamide
• 英文别名: N-methylanilide of benzoylacetic acid；3-oxo-3-phenyl-propionic acid-(N-methyl-anilide)；3-Oxo-3-phenyl-propionsaeure-(N-methyl-anilid)；Benzoylacet-N-methylanilid；N-Methyl-benzoylacetanilid；N-Methylbenzoylacetanilid
• CAS: 2665-92-1
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: XCQVOWLUKJEWAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-3-oxo-N,3-diphenylpropanamide 在 硫酸 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 反应 2.2h， 生成 3-hydroxy-1-methyl-4-phenylquinolin-2(1H)-one
  参考文献：
  名称：

  One-Pot Synthesis of 3-Hydroxyquinolin-2(1H)-ones from N-Phenylacetoacetamide via PhI(OCOCF₃)₂-Mediated α-Hydroxylation and H₂SO₄-Promoted Intramolecular Cyclization

  摘要：

  A clean, one-pot synthesis of the biologically important 3-hydroxyquinolin-2(1H)-one compounds has been realized from the readily available N-phenylacetoacetamide derivatives through a PhI(OCOCF3)(2)-mediated alpha-hydroxylation and a H2SO4-promoted intramolecular condensation. The hydroxyl group in the generated alpha-hydroxylated intermediate can be well tolerated in the second H2SO4-promoted cyclization step.

  DOI：

  10.1021/jo400541s
• 作为产物：
  描述：

  苯乙酮 在 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 生成 N-methyl-3-oxo-N,3-diphenylpropanamide
  参考文献：
  名称：

  Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination

  摘要：

  在CuI存在下，烯胺化合物与托格尼试剂发生反应，生成β-三氟甲基烯胺中间体，通过碘代苯（PhIO）介导的分子内氮杂环化反应，直接转化为具有生物学意义的三氟甲基化2H-氮杂环烯化合物，这是一个一锅法过程。

  DOI：

  10.3762/bjoc.14.123

文献信息

• One-pot dichlorinative deamidation of primary β-ketoamides
  作者：Congke Zheng、Xiaohui Zhang、Muhammad Ijaz Hussain、Mingming Huang、Qing Liu、Yan Xiong、Xiangming Zhu

  DOI：10.1016/j.tetlet.2016.12.087

  日期：2017.2

  An approach to the dichlorinative deamidation of primary β-ketoamides through ketonic cleavage is described, and a series of α,α-dichloroketones were furnished mostly in the presence of TEMPO. Based on control experiments, a mechanism involving tandem dichlorination and deamidation is proposed to interpret the observed reactivity.

  描述了一种通过酮裂解使伯-β-酮酰胺二氯化脱酰胺的方法，并且主要在TEMPO存在的情况下提供了一系列α，α-二氯酮。基于对照实验，提出了一种涉及串联二氯化和脱酰胺的机理来解释所观察到的反应性。
• Alkyne hydroarylation with Au N-heterocyclic carbene catalysts
  作者：Cristina Tubaro、Marco Baron、Andrea Biffis、Marino Basato

  DOI：10.3762/bjoc.9.29

  日期：——

  Mono- and dinuclear gold complexes with N-heterocyclic carbene (NHC) ligands have been employed as catalysts in the intermolecular hydroarylation of alkynes with simple unfunctionalised arenes. Both mono- and dinuclear gold(III) complexes were able to catalyze the reaction; however, the best results were obtained with the mononuclear gold(I) complex IPrAuCl. This complex, activated with one equivalent

  具有 N-杂环卡宾 (NHC) 配体的单核和双核金配合物已被用作炔烃与简单未官能化芳烃的分子间加氢芳基化的催化剂。单核和双核金 (III) 配合物都能够催化反应；然而，最好的结果是使用单核金 (I) 络合物 IPrAuCl 获得的。与更常用的钯 (II) 催化剂相比，这种用一当量四氟硼酸银活化的配合物在室温酸性条件下表现出更高的催化活性和选择性。此外，即使在中性条件下，该复合物也是活跃的，尽管程度较小，但与先前发布的复合 AuCl(PPh(3)) 相比，活性较低，但选择性更高。
• CERIUM (IV) MEDIATED OXIDATIVE DIMERIZATION OF 3-OXOACID ANILIDES AND THEIR CYCLIZATIONS
  作者：B. Zaleska、S. Lis

  DOI：10.1081/scc-100000198

  日期：2001.1

  Investigation of the behavior of several anilides of 3- oxoacids in oxidation reaction with ceric ammonium nitrate has shown that selective intermolecular C-C bond formation, which led to their dimers, is typical of these compounds. These dimeric species were cyclized in two routes, A and B, leading to 3-[2′-(1′-aniline-3′-oxo)-indene]-quinoline-2-on derivatives with HCl(g) (Route A), and with application

  对 3-含氧酸的几种苯胺在与硝酸铈铵的氧化反应中的行为的研究表明，选择性分子间 CC 键形成，导致它们的二聚体，是这些化合物的典型特征。这些二聚体在两条路线 A 和 B 中环化，产生 3-[2'-(1'-aniline-3'-oxo)-indene]-quinoline-2-on 衍生物与 HCl(g)（路线 A )，并使用 H2SO4 作为环化剂，得到呋喃-3,4-二羧酸衍生物（路线 B）。
• Selective α-amination and α-acylation of esters and amides via dual reactivity of O-acylhydroxylamines toward zinc enolates
  作者：Stacey L. McDonald、Qiu Wang

  DOI：10.1039/c3cc49296f

  日期：——

  Selective alpha-amination and alpha-acylation of esters and amides have been developed, employing O-acylhydroxylamines as a dually reactive aminating and acylating reagent. Treatment of zinc enolates with O-acylhydroxylamines provides solely 1,3-dicarbonyl compounds under mild conditions. Introduction of a copper catalyst into the system shifts the reactivity entirely, yielding alpha-amination products

  酯和酰胺的选择性α-胺化和α-酰化已经开发出来，采用O-酰基羟胺作为双反应性胺化和酰化试剂。用O-酰基羟胺处理烯醇锌可以在温和的条件下仅提供1,3-二羰基化合物。将铜催化剂引入系统会完全改变反应性，仅产生α-胺化产物。
• Effect of N-Alkyl on Formation of Quinolones from N-Alkylbenzoylacetanilides¹
  作者：C. F. KOELSCH、J. W. BRITAIN

  DOI：10.1021/jo01092a041

  日期：1959.10