N,N-diethyl-2-oxo-2-(m-tolyl)acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-diethyl-2-oxo-2-(m-tolyl)acetamide
• 英文别名: N,N-diethyl-2-(3-methylphenyl)-2-oxoacetamide
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: CGQUINYQJMSDDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-N,N-diethyl-3-m-tolylacrylamide 在 碘苯二乙酸 、 硫酸 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以48%的产率得到N,N-diethyl-2-oxo-2-(m-tolyl)acetamide
  参考文献：
  名称：

  无金属的串联氧化芳基迁移和C–C键裂解：由丙烯酸衍生物合成α-酮酰胺和酯

  摘要：

  已经发现了一种由高价碘试剂介导的新型无金属串联氧化芳基迁移/ CC键断裂反应。所提出的转变通过伴随CC键断裂的1，2-芳基转移的协同过程，使人们容易地从丙烯酸衍生物中直接获得重要的α-酮酰胺和α-酮酸酯衍生物。

  DOI：

  10.1021/ol502834g

文献信息

• Ligand-Free Pd-Catalyzed Double Carbonylation of Aryl Iodides with Amines to α-Ketoamides under Atmospheric Pressure of Carbon Monoxide and at Room Temperature
  作者：Hongyan Du、Qing Ruan、Minghao Qi、Wei Han

  DOI：10.1021/acs.joc.5b01249

  日期：2015.8.7

  A general Pd-catalyzed double carbonylation of aryl iodides with secondary or primary amines to produce α-ketoamides at atmospheric CO pressure has been developed. This transformation proceeds successfully even at room temperature and in the absence of any ligand and additive. A wide range of aryl iodides and amines can be coupled to the desired α-ketoamides in high yields with excellent chemoselectivities

  已经开发出在大气压CO压力下，普通的钯催化的碘化芳基碘与仲或伯胺的双羰基化反应，生成α-酮酰胺。即使在室温下且没有任何配体和添加剂的情况下，这种转化也能成功进行。各种各样的芳基碘化物和胺类可以以高收率与所需的α-酮酰胺以优异的化学选择性偶联。重要的是，目前的方法已被证明可用于生物活性分子和手性α-酮酰胺的合成。
• Visible-light-mediated direct access to α-ketoamides by dealkylative amidation of tertiary amines with benzoylformic acids
  作者：Zhiguo Zhang、Fangnan Liu、Jingwen Chen、Kai Zhou、Zongbi Bao、Baogen Su、Qiwei Yang、Qilong Ren、Yiwen Yang

  DOI：10.1016/j.tetlet.2019.151191

  日期：2019.10

  visible-light induced direct amidation of benzoylformic acids with tertiary amines has been explored. Tertiary amines underwent N-dealkylative amidation with α-keto acid in the presence of [IrdFCF3ppy}2(bpy)]PF6 and Cs2CO3, affording the corresponding α-ketoamides in good yields under mild conditions. This transformation exhibits a wide substrate scope and provides a facile synthetic approach to α-ketoamides

  已经研究了可见光诱导的苯甲酰基甲酸与叔胺的直接酰胺化。叔胺在[Ir dFCF 3 ppy} 2（bpy）] PF 6和Cs 2 CO 3的存在下用α-酮酸进行N-脱烷基酰胺化反应，在温和条件下以良好的收率得到相应的α-酮酰胺。这种转化表现出广泛的底物范围，并为α-酮酰胺提供了一种简便的合成方法。
• Aryl-palladium-NHC complex: efficient phosphine-free catalyst precursors for the carbonylation of aryl iodides with amines or alkynes
  作者：Chunyan Zhang、Jianhua Liu、Chungu Xia

  DOI：10.1039/c4ob01878h

  日期：——

  aryl-palladium-NHC compounds was prepared according to the reported methods and their catalytic activity in the carbonylation of aryl iodides to synthesize α-keto amides and alkynones was examined. These practical aryl-palladium-NHC complexes have shown highly efficient catalyzed carbonylation and Sonogashira carbonylation reactions, with high turnover number in synthesis of α-keto amides (TON = 4300) and in synthesis

  根据报道的方法制备了一系列芳基-钯-NHC化合物，并研究了它们在芳基碘化物羰基化反应中合成α-酮酰胺和炔烃的催化活性。这些实用的芳基-钯-NHC配合物已显示出高效的催化羰基化和Sonogashira羰基化反应，在合成α-酮酰胺（TON = 4300）和炔烃（TON = 980）时具有很高的转化率。
• Cu(<scp>i</scp>)-Functionalized SBA-16: an efficient catalyst for the synthesis of α-ketoamides under moderate conditions
  作者：Xueyao Zhang、Honglei Yang、Yong Huo、Jing Li、Jianxin Ma、Jiantai Ma

  DOI：10.1039/c5dt04969e

  日期：——

  An efficient catalyst based on the cage-like mesoporous material SBA-16 as the support and Cu(I) as active sites has been successfully prepared. The catalyst demonstrated high catalytic activity (up to 88%) in the direct oxidative synthesis of α-ketoamides between acetophenone and piperidine, employing O2 from open air as the oxidant without other additives. A heterogeneous catalyst was applied in this reaction for the first time, and the catalyst could be easily separated from the reaction system by filtration and reused several times without a significant loss of activity.

  一种高效催化剂已成功制备，以笼状介孔材料SBA-16作为载体，以Cu(I)作为活性位点。该催化剂在乙酰苯与哌啶的直接氧化合成α-酮酰胺中表现出高催化活性（高达88%），采用开空气中的O2作为氧化剂，无需其他添加剂。这种反应首次使用了异相催化剂，催化剂可以通过过滤轻松从反应体系中分离，并在未显著失活的情况下多次重复使用。
• Metal-Free Tandem Oxidative Aryl Migration and C–C Bond Cleavage: Synthesis of α-Ketoamides and Esters from Acrylic Derivatives
  作者：Le Liu、Liang Du、Daisy Zhang-Negrerie、Yunfei Du、Kang Zhao

  DOI：10.1021/ol502834g

  日期：2014.11.7

  novel tandem metal-free oxidative aryl migration/C–C bond-cleavage reaction, mediated by hypervalent iodine reagent, has been discovered. The presented transformation provided straightforward access to important α-ketoamide and α-ketoester derivatives from readily available acrylic derivatives via a concerted process of 1,2-aryl shift concomitant with C–C bond cleavage.

  已经发现了一种由高价碘试剂介导的新型无金属串联氧化芳基迁移/ CC键断裂反应。所提出的转变通过伴随CC键断裂的1，2-芳基转移的协同过程，使人们容易地从丙烯酸衍生物中直接获得重要的α-酮酰胺和α-酮酸酯衍生物。