1-morpholino-2-(3-nitrophenyl)ethane-1,2-dione | 1391739-32-4

• 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: 1-morpholino-2-(3-nitrophenyl)ethane-1,2-dione
• 英文别名: 1-Morpholin-4-yl-2-(3-nitrophenyl)ethane-1,2-dione；1-morpholin-4-yl-2-(3-nitrophenyl)ethane-1,2-dione
• CAS: 1391739-32-4
• 化学式: C₁₂H₁₂N₂O₅
• 分子量: 264.238
• InChiKey: YRSMZEPTVLOADD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吗啉 、 3-硝基苯乙醇 在 2,2,6,6-四甲基哌啶氧化物 、 potassium carbonate 、 copper(I) bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以39%的产率得到1-morpholino-2-(3-nitrophenyl)ethane-1,2-dione
  参考文献：
  名称：

  Copper–TEMPO-catalyzed synthesis of α-ketoamides via tandem sp³C–H aerobic oxidation and amination of phenethyl alcohol derivatives

  摘要：

  首次成功合成了从苯乙醇衍生物中获得的α-酮酰胺，这是一种简单且易获得的底物。

  DOI：

  10.1039/c6ob01387b

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。
• NIS-Catalyzed Reactions: Amidation of Acetophenones and Oxidative Amination of Propiophenones
  作者：Manjunath Lamani、Kandikere Ramaiah Prabhu

  DOI：10.1002/chem.201202703

  日期：2012.11.12

  Single‐step amination: The N‐iodosuccinimide (NIS)‐catalyzed amidation of acetophenone derivatives by using tert‐butylhydroperoxide (TBHP) as an oxidant is presented. A variety of acetyl derivatives of heterocyclic compounds were easily converted to their corresponding ketoamides under these conditions. A new, NIS‐catalyzed amination of propiophenone and its derivatives in the presence of TBHP to furnish

  单步胺化：介绍了使用叔丁基过氧化氢（TBHP）作为氧化剂的N-碘琥珀酰亚胺（NIS）催化的苯乙酮衍生物酰胺化反应。在这些条件下，杂环化合物的各种乙酰基衍生物很容易转化为它们相应的酮酰胺。在TBHP存在下，一种新的NIS催化的苯乙酮及其衍生物的胺化反应可提供相应的2-氨基酮衍生物，这是首次报道的苯乙酮衍生物的单步胺化反应。
• 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。
• A two-step continuous synthesis of α-ketoamides and α-amino ketones from 2° benzylic alcohols using hydrogen peroxide as an economic and benign oxidant
  作者：Chengkou Liu、Zheng Fang、Zhao Yang、Qingwen Li、Shiyu Guo、Kai Guo

  DOI：10.1039/c5ra27653e

  日期：——

  A practical two-step synthesis of α-ketoamides and α-amino ketones via direct oxidative coupling between 2° benzylic alcohols and amines was developed. Hydrogen peroxide, an economic and environmentally friendly oxidant, was used, and a metal catalyst was unnecessary. Moreover, the continuous-flow technique was employed to increase the functional group tolerance, efficiency and safety.

  开发了一种实用的两步合成法，即通过2°苄醇与胺之间的直接氧化偶合来合成α-酮酰胺和α-氨基酮。使用了经济和环境友好的氧化剂过氧化氢，并且不需要金属催化剂。而且，采用连续流技术来增加官能团的耐受性，效率和安全性。
• Ligand-free Zn-catalyzed double carbonylation of aryl iodides with secondary amines: A simple and efficient approach to access α-ketoamides
  作者：Vimala Pitti、Markandeya Sarma Vangala、Sridhar Chidara、Padma Mogili

  DOI：10.1080/00397911.2021.2012805

  日期：2022.1.17

  Abstract Herein, we report a Zinc catalyzed double carbonylation of aryl iodides with secondary amines under CO pressure for the synthesis of α-ketoamides in good to excellent yields. This methodology provides a simple and economic approach to derivatize useful α-ketoamides.

  摘要 在此，我们报道了在 CO 压力下锌催化芳基碘化物与仲胺的双羰基化反应，以良好至优异的产率合成 α-酮酰胺。该方法提供了一种简单且经济的方法来衍生有用的 α-酮酰胺。