N-benzyl-2-(4-chlorophenyl)-2-oxoacetamide

• 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-benzyl-2-(4-chlorophenyl)-2-oxoacetamide
• 化学式: C₁₅H₁₂ClNO₂
• mdl: MFCD19339049
• 分子量: 273.719
• InChiKey: HJVCTBIUHBZENT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 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：

  N-benzyl-2-(4-chlorophenyl)-2-oxoacetamide 在 a-无水葡萄糖酯 、 Candida parapsilosis ATCC 7330 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以24%的产率得到
  参考文献：
  名称：

  Biocatalytic reduction of α-keto amides to (R)-α-hydroxy amides using Candida parapsilosis ATCC 7330

  摘要：

  Biocatalytic reduction of primary and secondary alpha-keto amides was accomplished using whole cells of Candida parapsilosis ATCC 7330. The primary (R)-alpha-hydroxy amides were obtained in good enantiomeric excess (up to 94%) and conversion (88-99%) as compared to the secondary (R)-alpha-hydroxy amides. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cattod.2012.03.081
• 作为产物：
  描述：

  对氯扁桃酸 在 calcium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 作用下， 生成 N-benzyl-2-(4-chlorophenyl)-2-oxoacetamide
  参考文献：
  名称：

  Biocatalytic reduction of α-keto amides to (R)-α-hydroxy amides using Candida parapsilosis ATCC 7330

  摘要：

  Biocatalytic reduction of primary and secondary alpha-keto amides was accomplished using whole cells of Candida parapsilosis ATCC 7330. The primary (R)-alpha-hydroxy amides were obtained in good enantiomeric excess (up to 94%) and conversion (88-99%) as compared to the secondary (R)-alpha-hydroxy amides. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cattod.2012.03.081

文献信息

• Diversification of α-ketoamides <i>via</i> transamidation reactions with alkyl and benzyl amines at room temperature
  作者：Shweta Singh、Sureshbabu Popuri、Qazi Mohammad Junaid、Shahulhameed Sabiah、Jeyakumar Kandasamy

  DOI：10.1039/d1ob01021b

  日期：——

  A wide range of N-tosyl α-ketoamides underwent transamidation with various alkyl and benzyl amines in the absence of a catalyst or base at room temperature. On the other hand, transamidation in N-Boc α-ketoamides was achieved in the presence of Cs₂CO₃.

  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。
• Visible-light-mediated metal-free decarboxylative acylations of isocyanides with α-oxocarboxylic acids and water leading to α-ketoamides
  作者：Yufen Lv、Pengli Bao、Huilan Yue、Jiang-Sheng Li、Wei Wei

  DOI：10.1039/c9gc03253c

  日期：——

  An efficient visible-light-promoted approach for preparing α-ketoamides from α-oxocarboxylic acids, isocyanides and water is disclosed. The present transformation could be achieved under mild and metal-free conditions through a sequence of decarboxylation, radical addition and hydration processes, which provides a novel and facile route to construct α-ketoamides from simple and readily available chemical

  公开了一种由可见光促进的有效方法，其由α-氧代羧酸，异氰酸酯和水制备α-酮酰胺。通过一系列的脱羧，自由基加成和水合过程，可以在温和且无金属的条件下实现本发明的转化，这为从简单易得的化学原料制备α-酮酰胺提供了一种新颖而便捷的途径。
• Asymmetric Aerobic Oxidation of α-Hydroxy Acid Derivatives Catalyzed by Reusable, Polystyrene-Supported Chiral N-Salicylidene Oxidovanadium tert-Leucinates
  作者：Santosh B. Salunke、N.Seshu Babu、Chien-Tien Chen

  DOI：10.1002/adsc.201100062

  日期：2011.5

  The direct immobilization of two different C‐5‐propargyl ether‐modified, chiral N‐salicylidene vanadyl(V) tert‐leucinates onto 4‐azidomethyl‐substituted polystyrene by click chemistry was examined. Among the eight different solvents investigated, the resulting polystyrene‐supported catalysts promote the asymmetric, aerobic oxidation of α‐hydroxy (thio)esters and amides with enantioselectivities of

  通过点击化学方法研究了将两种不同的C-5-炔丙基醚改性的手性N-水杨基亚烷基钒（V）叔亮氨酸酯直接固定在4-叠氮基甲基取代的聚苯乙烯上的方法。在所研究的八种不同溶剂中，所得的聚苯乙烯负载催化剂促进了α-羟基（硫代）酯和酰胺的不对称，好氧氧化，其在氯仿中的对映选择性高达99％ee（选择性高达41）。这些聚苯乙烯负载的催化剂可以很容易地通过过滤回收，并至少连续四次重复使用，而不会损失反应性和对映选择性。
• Simplified Procedure for TEMPO-Catalyzed Oxidation: Selective Oxidation of Alcohols, <font>α</font>-Hydroxy Esters, and Amides Using TEMPO and Calcium Hypochlorite
  作者：Sabbasani Rajasekhara Reddy、Selvaraj Stella、Anju Chadha

  DOI：10.1080/00397911.2011.584650

  日期：2012.12.1

  Abstract A wide range of primary and secondary multifunctional alcohols, α-hydroxyamides, and α-hydroxyesters were oxidized to their corresponding aldehydes, ketones, α-ketoamides, and α-ketoesters under mild reaction conditions using 2,2,6,6-tetramethylpiperidine-1-oxyl as a catalyst with calcium hypochlorite as an oxidant [TEMPO-Ca(OCl)2]. This simplified method does not require any transition metals

  摘要 在温和的反应条件下，使用 2,2,6,6-四甲基哌啶将多种伯多官能团醇、α-羟基酰胺和 α-羟基酯氧化成相应的醛、酮、α-酮酰胺和 α-酮酯。 -1-氧基作为催化剂，次氯酸钙作为氧化剂[TEMPO-Ca(OCl)2]。这种简化的方法不需要任何过渡金属、酸或碱，并且展示了结构多样的醇的受控和选择性氧化，在室温下提供中等至极好的收率。图形概要
• Selective amidation by a photocatalyzed umpolung reaction
  作者：Debasish Ghosh、Rajesh Nandi、Saikat Khamarui、Sukla Ghosh、Dilip K. Maiti

  DOI：10.1039/c9cc01079c

  日期：——

  Herein, a metal-catalyzed organic transformation merged with another organophotocatalyst has been developed under mild conditions for the production of α-ketoamides.

  在此，已经开发了一种金属催化的有机转化，与另一种有机光催化剂在温和条件下结合，用于生产α-酮酰胺。