tert-butyl 4-(2-oxo-2-phenylacetyl)piperazine-1-carboxylate | 1389334-27-3

• 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: tert-butyl 4-(2-oxo-2-phenylacetyl)piperazine-1-carboxylate
• 英文别名: Tert-butyl 4-(2-oxo-2-phenylacetyl)piperazine-1-carboxylate
• CAS: 1389334-27-3
• 化学式: C₁₇H₂₂N₂O₄
• 分子量: 318.373
• InChiKey: YANMAEXXFSHJHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苏合香醇 在 叔丁基过氧化氢 、 copper(l) iodide 、 氧气 作用下， 以 neat (no solvent) 为溶剂， 反应 59.0h， 生成 tert-butyl 4-(2-oxo-2-phenylacetyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Copper-Catalyzed One-Pot Synthesis of α-Ketoamides from 1-Arylethanols

  摘要：

  A copper-catalyzed one-pot strategy for the synthesis of -ketoamides from 1-arylethanols is described. This triple oxidation of 1-arylethanols involves alcohol oxidation, sp(3) C-H oxidation, and oxidative amidation with amines. The protocol is highly efficient, delivering -ketoamides in good to excellent yields.

  DOI：

  10.1055/s-0034-1379975

文献信息

• Coupling of Methyl Ketones and Primary or Secondary Amines Leading to α-Ketoamides
  作者：Wei Wei、Ying Shao、Huayou Hu、Feng Zhang、Chao Zhang、Yuan Xu、Xiaobing Wan

  DOI：10.1021/jo301117b

  日期：2012.9.7

  A metal-free oxidative coupling of methyl ketones and primary or secondary amines to α-ketoamides has been developed. Four intermediates, α-iodoketone, α-aminoketone, iminium intermediate, and α-hydroxy amine have been identified through a series of control experiments. The atom-economic methodology can be scaled-up, tolerates a variety of functional groups, and is operationally simple.

  已经开发出甲基酮和伯或仲胺与α-酮酰胺的无金属氧化偶联。通过一系列对照实验，已鉴定出四种中间体，即α-碘酮，α-氨基酮，亚胺鎓中间体和α-羟胺。原子经济方法可以扩大规模，可以容忍各种官能团，并且操作简单。
• Solvent-free one-pot oxidation of ethylarenes for the preparation of α-ketoamides under mild conditions
  作者：Fuyan Liu、Kuan Zhang、Yanfeng Liu、Shan Chen、Yiping Chen、Dela Zhang、Chunfu Lin、Bo Wang

  DOI：10.1039/c6ra26679g

  日期：——

  Here we developed a highly efficient solvent-free, one-pot procedure for synthesizing α-ketoamides from ethylarenes and amines, by oxidizing a C–H bond sp3 center. A copper catalyst was employed, and the reactions proceeded smoothly at ambient temperatures. Most of the tested ethylarenes and amines were successfully converted to their corresponding α-ketoamides in moderate to excellent yields of up

  在这里，我们开发了一种高效的无溶剂一锅法，可通过氧化C–H键的sp 3中心从乙基芳烃和胺合成α-酮酰胺。使用铜催化剂，并且反应在环境温度下顺利进行。在三当量的氧化剂叔丁基氢过氧化物的作用下，大多数被测试的乙基芳烃和胺都成功地以中等至优异的收率成功转化为它们相应的α-酮酰胺，收率高达93％。
• A general metal free approach to α-ketoamides via oxidative amidation–diketonization of terminal alkynes
  作者：Ramesh Deshidi、Manjeet Kumar、Shekaraiah Devari、Bhahwal Ali Shah

  DOI：10.1039/c4cc03783a

  日期：——

  A metal free catalytic system employing TMSOTf/I₂/DMSO for the oxidative amidation–diketonization of terminal alkynes, in order to produce a wide variety of α-ketoamides, has been developed.

  使用TMSOTf/I2/DMSO作为金属无催化体系，用于终端炔烃的氧化酰胺化-二酮化反应，以产生各种α-酮酰胺。
• Iodine-Promoted Oxidative Amidation of Terminal Alkenes - Synthesis of α-Ketoamides, Benzothiazoles, and Quinazolines
  作者：Ramesh Deshidi、Shekaraiah Devari、Bhahwal Ali Shah

  DOI：10.1002/ejoc.201403547

  日期：2015.3

  A novel metal-free strategy for oxidative amidation of terminal alkenes by using I2/DMSO for the synthesis of α-ketoamides has been developed. Intriguingly, the use of tert-butylhydroperoxide (TBHP) as co-oxidant can facilitate the synthesis of α-ketoamides at room temperature without any solvent, thereby making it a green protocol. The reaction with primary amines can be easily achieved by using SeO2

  通过使用 I2/DMSO 合成 α-酮酰胺，开发了一种新的无金属氧化酰胺化末端烯烃策略。有趣的是，使用叔丁基过氧化氢 (TBHP) 作为助氧化剂可以在室温下促进 α-酮酰胺的合成，无需任何溶剂，从而使其成为一种绿色方案。使用 SeO2 作为氧化剂可以很容易地实现与伯胺的反应。此外，该方法的范围还扩展到苯并噻唑啉和喹唑啉的合成。
• I₂-promoted aerobic oxidative coupling of acetophenes with amines under metal-free conditions: facile access to α-ketoamides
  作者：Shiyu Guo、Zheng Fang、Zhao Yang、Chengkou Liu、Zhongxue Dai、Lihuan Zhao、Kai Guo

  DOI：10.1039/c5ra24062j

  日期：——

  A novel and efficient I2-promoted oxidative coupling of acetophenes with amines to α-ketoamides is presented, which employs O2 as an environmentally friendly oxidant under metal-free conditions. Based on a series of control experiments and radical trapping experiments, plausible reaction mechanism was proposed and iminium ion was identified as a significant intermediate in this process. This methodology

  提出了一种新颖而有效的I 2促进的乙炔与胺氧化成α-酮酰胺的方法，该方法在无金属条件下采用O 2作为环境友好型氧化剂。基于一系列的控制实验和自由基捕获实验，提出了合理的反应机理，并确定了亚胺离子是该过程的重要中间体。这种方法是一种可行的，温和的方法，以高收率生产α-酮酰胺。