N,N-diisopropyl-2-oxo-2-phenylacetamide | 51804-83-2

• 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-diisopropyl-2-oxo-2-phenylacetamide
• 英文别名: N,N-diisopropylphenylglyoxylamide；N,N-diisopropylbenzoylformamide；2-oxo-2-phenyl-N,N-di(propan-2-yl)acetamide
• CAS: 51804-83-2
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: MQIXFTPQCOPXKA-UHFFFAOYSA-N

物化性质

• 熔点：
  125.0-125.5 °C(Solv: hexane (110-54-3))
• 沸点：
  323.3±25.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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,N-diisopropyl-2-oxo-2-phenylacetamide 在 sodium tetrahydroborate 作用下， 反应 120.0h， 以24%的产率得到N,N-diisopropyl-2-hydroxy-2-phenylpentanamide
  参考文献：
  名称：

  Toda, Fumio; Kiyoshige, Koji; Yagi, Minoru, Angewandte Chemie, 1989, vol. 101, # 3, p. 329 - 330

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苯基-N,N-二(丙-2-基)乙酰胺 在 air 、 四丁基溴化铵 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以82%的产率得到N,N-diisopropyl-2-oxo-2-phenylacetamide
  参考文献：
  名称：

  Cesium carbonate promoted aerobic oxidation of arylacetamides: an efficient access to N-substituted α-keto amides

  摘要：

  A novel cesium carbonate promoted aerobic oxidation reaction to prepare N-substituted alpha-keto amides in the presence of catalytic amount of tetra-n-butylammonium bromide was described. This reaction provides a very simple and convenient route from easily available arylacetamides in good to high yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.099

文献信息

• 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。
• Reactions of a Carbamoylstannane with Acid Chlorides:  Highly Efficient Synthesis of α-Oxo Amides
  作者：Ruimao Hua、Hide-aki Takeda、Yoshimoto Abe、Masato Tanaka

  DOI：10.1021/jo035572r

  日期：2004.2.1

  Treatment of acid chlorides with a carbamoylstannane under mild conditions (mostly rt for a few hours) affords α-oxo amides in high yields. Vicinal polycarbonyl compounds are also obtained, although spontaneous decarbonylation occasionally occurs.

  在温和的条件下（通常在室温下几个小时），用氨基甲酰基锡烷处理酰基氯，可以高收率得到α-氧代酰胺。尽管偶尔会发生自发的脱羰作用，但也可以得到近邻的多羰基化合物。
• Generation and Reaction of Carbamoyl Anions in Flow: Applications in the Three-Component Synthesis of Functionalized α-Ketoamides
  作者：Aiichiro Nagaki、Yusuke Takahashi、Jun-ichi Yoshida

  DOI：10.1002/anie.201601386

  日期：2016.4.18

  microreactor system, carbamoyllithium compounds were successfully generated and used for reactions with electrophiles to give various amides, including α‐ketoamides. The present method could be applied to the three‐component synthesis of functionalized α‐ketoamides using a carbamoyllithium compound, methyl chloroformate, and a functionalized organolithium reagent.

  使用流动微反应器系统，成功生成了氨基甲酰基锂化合物，并将其用于与亲电试剂反应以生成各种酰胺，包括α-酮酰胺。本方法可用于使用氨基甲酰基锂化合物，氯甲酸甲酯和功能化有机锂试剂的三组分合成功能化α-酮酰胺。
• Direct Formation of the Carbonyl Anion of Diisopropyl Formamide
  作者：Robert R. Fraser、Patrick R. Hubert

  DOI：10.1139/v74-029

  日期：1974.1.1

  the carbonyl anion, LiCON[CH(CH3)2]2. Reactions of this anion with benzaldehyde, benzophenone, ethyl benzoate, acetone, and propionaldehyde occur in yields ranging from 30–92%. Thus, this anion provides a useful method for the synthesis of α-hydroxy and α-keto acids, particularly in cases where cyanohydrin formation is difficult.

  二异丙基甲酰胺与二异丙基氨基锂的反应通过夺取甲酰基质子产生羰基阴离子 LiCON[CH(CH3)2]2。该阴离子与苯甲醛、二苯甲酮、苯甲酸乙酯、丙酮和丙醛的反应产率为 30-92%。因此，这种阴离子为合成 α-羟基和 α-酮酸提供了一种有用的方法，特别是在难以形成氰醇的情况下。
• Direct formation, and reactions of a carbonyl anion free from competitive nucleophiles
  作者：Keith Smith、Kalyanaraman Swaminathan

  DOI：10.1039/c39760000387

  日期：——

  At low temperature, in tetrahydrofuran (THF)–ether-pentane, ButLi abstracts a proton from bis(isopropyl)formamide to give LiCONPri2, which reacts with carbonyl compounds to give high yields of α-hydroxyamides.

  在低温下，Bu t Li在四氢呋喃（THF）-醚-戊烷中从双（异丙基）甲酰胺中提取出一个质子，生成LiCONPr i 2，LiCONPr i 2与羰基化合物反应生成高产率的α-羟基酰胺。