N-methyl-2-oxo-2-phenylacetamide | 141694-35-1

• 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-methyl-2-oxo-2-phenylacetamide
• 英文别名: N-methyl-2-oxo-2-(p-tolyl)acetamide；N-methyl-2-(4-methylphenyl)-2-oxoacetamide
• CAS: 141694-35-1
• 化学式: C₁₀H₁₁NO₂
• mdl: MFCD19313701
• 分子量: 177.203
• InChiKey: WBCYCENQQJJKFC-UHFFFAOYSA-N

物化性质

• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 N-methyl-2-oxo-2-phenylacetamide 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到tert-butyl methyl(2-oxo-2-(p-tolyl)acetyl)carbamate
  参考文献：
  名称：

  Diversification of α-ketoamides via transamidation reactions with alkyl and benzyl amines at room temperature

  摘要：

  一系列的N-对甲苯磺酰基α-酮酰胺在室温下在没有催化剂或碱的情况下与各种烷基和苄胺发生了转酰胺化反应。另一方面，N-叔丁氧羰基α-酮酰胺的转酰胺化反应是在Cs2CO3存在的情况下实现的。

  DOI：

  10.1039/d1ob01021b
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以79%的产率得到N-methyl-2-oxo-2-phenylacetamide
  参考文献：
  名称：

  氨基甲酰硅烷通过酰氯的氨基羰基化制备仲α-酮酰胺的简便方法

  摘要：

  描述了通过酰基氯与N-甲氧基甲基-N-甲基氨基甲酰基（三甲基）硅烷的氨基羰基化将酰基氯方便地转化为相应的仲α-酮酰胺。含有甲氧基甲基的氨基甲酰基硅烷的使用避免了在氨基羰基化反应中α-酮酰胺产物与氨基甲酰基硅烷原位反应。甲氧基甲基用作氨基保护基，可通过简单的酸水解容易地转化为氢原子。

  DOI：

  10.1016/j.tetlet.2016.10.040

文献信息

• 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。
• Organocatalyzed Asymmetric Aldol Reaction of α-Keto Amides with A Tripeptide Catalyst
  作者：Yoshihito Kohari、Kazumasa Kon、Hiromu Takai、Takumu Kobayashi、Miki Murata

  DOI：10.1055/a-1380-6436

  日期：2021.5

  An organocatalyzed asymmetric aldol reaction of α-keto amides was developed. An N-terminal 4-trans-siloxyproline-based tripeptide with an l-tert-leucine unit adjacent to the 4-trans-siloxyproline residue was used to catalyze the reaction between various α-keto amides and acetone, to produce the corresponding aldol adducts with up to 99% yield and 91% ee.

  开发了有机催化的α-酮酰胺的不对称醛醇缩合反应。具有与4-反式-硅烷氧基脯氨酸残基相邻的l-叔亮氨酸单元的N-末端基于4-反式-甲硅烷氧基脯氨酸的三肽被用来催化各种α-酮酰胺和丙酮之间的反应，以产生相应的醛醇加合物。产率高达99％，ee高达91％。
• nBu₄NI-Mediated oxidation of methyl ketones to α-ketoamides: using ammonium, primary and secondary amine-salt as an amine moiety
  作者：Dan Wang、Kuan Zhang、Luhan Jia、Danting Zhang、Yue Zhang、Yujia Cheng、Chang Lin、Bo Wang

  DOI：10.1039/c7ob00270j

  日期：——

  Presented here is the first example of synthesizing an array of primary-, secondary-, and tertiary-α-ketoamides with a non-metal catalyst nBu4NI from methyl ketones and inexpensive readily available amine/ammonium salts; the reactions proceeded smoothly under mild conditions, TBHP was used as an oxidant and the corresponding α-ketoamides were afforded in moderate to excellent yields.

  这是从甲基酮和廉价的容易得到的胺/铵盐合成带有非金属催化剂n Bu 4 NI的一系列伯，仲和叔α-酮酰胺的第一个例子。在温和的条件下，反应平稳进行，使用TBHP作为氧化剂，并以中等至极好的收率提供了相应的α-酮酰胺。
• .alpha.-Keto Amides and 1,2-Diketones from N,N'-Dimethoxy-N,N'-dimethylethanediamide. A Synthetic and Mechanistic Investigation
  作者：Mukund P. Sibi、Mali Marvin、Rajiv Sharma

  DOI：10.1021/jo00121a021

  日期：1995.8

  N,N'-Dimethoxy-N,N'-dimethylethanediamide (1), a 1,2-dicarbonyl synthon prepared from oxalyl chloride, undergoes nucleophilic displacements with Grignard reagents to provide alpha-keto amides 2-12 in 28-90% yields. The synthon also undergoes double nucleophilic displacements with organolithium reagents to furnish symmetrical 1,2-diketones 15-23 in 15-84% yields. A mechanism accounting for all the products from the reaction of 1 with nucleophiles has been proposed. Several control experiments were carried out to support the proposed mechanism.
• N,N′-Dimethoxy-N,Nt́-Dimethylethanediamide: A Useful α-Oxo-N-Methoxy-N-Methylamide and 1,2-Diketone Synthon
  作者：Mukund P. Sibi、Rajiv Sharma、Kevin L. Paulson

  DOI：10.1016/0040-4039(92)88108-h

  日期：1992.4

  N,N'-Dimethoxy-N,N'-dimethylethanediamide on treatment with one to two equivalents of alkyl, aryl, and benzyl Grignard reagents provide alpha-oxo-N-methoxy-N-methylamides in good to excellent yields and on reaction with excess aryllithiums furnish moderate to good yields of symmetrical 1,2-diarylketones.