N-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-N-methylacetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: N-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-N-methylacetamide
• 英文别名: N-(benzotriazol-1-ylmethyl)-N-methylacetamide
• 化学式: C₁₀H₁₂N₄O
• 分子量: 204.231
• InChiKey: PKFLFGIYZQCFMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-甲基乙酰胺 、 1H-苯并三唑-1-甲醇 以 溶剂黄146 为溶剂， 反应 24.0h， 以77%的产率得到N-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-N-methylacetamide
  参考文献：
  名称：

  The conversion of secondary into tertiary amides using benzotriazole methodology

  摘要：

  N-Alkyl-N-[1-(benzotriazol-1-yl)alkyl]amides, easily prepared from benzotriazole, an aldehyde, and a secondary amide, react readily with organozinc reagents to give tertiary amides in moderate to good yields. They are also reduced by LiAlH4 to afford tertiary amines.

  DOI：

  10.1021/jo00060a025

文献信息

• Iron-catalyzed C–N bond formation via oxidative Csp3–H bond functionalization adjacent to nitrogen in amides and anilines: Synthesis of N-alkyl and N-benzyl azoles
  作者：G. Saidulu、R. Arun Kumar、K. Rajender Reddy

  DOI：10.1016/j.tetlet.2015.05.048

  日期：2015.7

  Iron catalyzed oxidative protocol was developed to couple azoles with amides to generate N-alkylazole derivatives in moderate to excellent yields using tertiarybutyl hydroperoxide as an oxidant under mild reaction conditions. Furthermore, this protocol explored to couple azoles with N-alkylanilines, unexpectedly N-benzyl azoles were obtained as major products under these oxidative conditions.

  开发了铁催化的氧化方案，使用叔丁基过氧化氢作为氧化剂，在温和的反应条件下，将唑类与酰胺偶联，以中等至极好的收率生成N-烷基唑衍生物。此外，该方案探索了将唑与N-烷基苯胺偶联，在这些氧化条件下出乎意料地获得了N-苄基唑作为主要产物。
• A Metal-Free Cross-Dehydrogenative Coupling Reaction of Amides to Access N-Alkylazoles
  作者：Shengmei Guo、Hu Cai、Zheng Zhu、Yufeng Wang、Mingmeng Yang、Ling Huang、Jiuhan Gong

  DOI：10.1055/s-0036-1588307

  日期：——

  An iodine-catalyzed cross-dehydrogenative coupling reaction of N-alkyl amides and azoles is reported. The catalytic system provides an efficient method for introducing amides onto azoles, especially onto benzotriazoles.

  报道了碘催化的 N-烷基酰胺和唑类的交叉脱氢偶联反应。该催化体系提供了一种将酰胺引入唑类，尤其是苯并三唑类的有效方法。
• Metal-free Cross-Dehydrogenative Coupling of <i>HN</i>-azoles with α-C(sp³)-H Amides via C–H Activation and Its Mechanistic and Application Studies
  作者：Hariprasad Aruri、Umed Singh、Mukesh Kumar、Sumit Sharma、Sravan Kumar Aithagani、Vivek K. Gupta、Serge Mignani、Ram A. Vishwakarma、Parvinder Pal Singh

  DOI：10.1021/acs.joc.6b02448

  日期：2017.1.20

  A metal-free one step coupling reaction between various N-azole rings and diverse α-C(sp3)-H containing amides has been developed under oxidative reaction conditions. Commercially available tetrabutyl ammonium iodide (TBAI) in the presence of terbutylhydroperoxide (TBHP), under neat reaction condition, efficiently catalyzed the coupling. Various azole types, such as 1H-benzotriazoles, 1H-1,2,3-triazoles

  在氧化反应条件下，已开发出各种N-唑环与各种含α-C（sp 3）-H的酰胺之间的无金属一步偶联反应。在纯净的反应条件下，在叔丁基过氧化氢（TBHP）存在下，市售的碘化四丁基碘化铵（TBAI）有效地催化了偶联反应。各种唑类型，例如1 H-苯并三唑，1 H -1,2,3-三唑，1 H -1,2,4-三唑，1 H-四唑，1 H-吡唑和1 H-苯并咪唑，和含α-C（sp 3）-H的酰胺，例如N，N-二甲基乙酰胺，N，Ñ二甲基苯甲酰胺，Ñ甲基乙酰胺，Ñ，Ñ -diethylacetamide，Ñ -甲基吡咯烷和吡咯烷-2-酮，被成功地用于偶联。为了研究不同中间体的参与，还进行了一系列设计和控制的实验。根据证据，还提出了一个合理的机制。这些新颖，简单，快速，有吸引力和直接的转变为构造新型高度功能化的N开辟了道路。-唑类通过直接的共价N–H键转换为N–C键而形成。该方法允许使用经典的合成方法合成需要多个步骤的复杂分子。此外，含α-C（sp
• Iron Nanoparticles Embedded in Graphitic Carbon Matrix as Heterogeneous Catalysts for the Oxidative C−N Coupling of Aromatic N−H Compounds and Amides
  作者：Jinbao He、Amarajothi Dhakshinamoorthy、Ana Primo、Hermenegildo Garcia

  DOI：10.1002/cctc.201700429

  日期：2017.8.9

  particle size ranging from 10.9 to 26.5 nm embedded in turbostratic graphitic carbon matrix have been prepared by pyrolysis at 900 °C under inert atmosphere of chitosan powders containing Fe2+ and Co2+ ions in various proportions. The resulting Fe/Co NP@C samples have been evaluated as heterogeneous catalysts for the oxidative C−N coupling of amides and aromatic N−H compounds. It was observed that sequential

  通过在900°C的惰性气氛下于900°C的温度下热解制备了Fe或Co纳米颗粒（NPs）和两种纳米颗粒的Fe / Co原子比不同的Fe-Co合金，它们的平均粒径在10.9至26.5 nm之间，并嵌入涡轮层状石墨碳基质中。含有不同比例的Fe 2+和Co 2+离子的壳聚糖粉末。所得的Fe / Co NP @ C样品已被评估为酰胺和芳族N-H化合物氧化C-N偶联的非均相催化剂。观察到，当过量添加N，N时，连续添加了两个等分的叔丁基氢过氧化物（TBHP）。‐二甲基乙酰胺（DMA）作为溶剂可高产率提供相应的偶联产物，而最有效的催化剂是Fe NP @ C。Fe NP @ C具有可重复使用性和广泛的应用范围。通过使用高纯度的铁盐并观察到故意添加Cu 2+杂质甚至对催化活性产生不利影响，可以支持Fe的催化活性。通过用2,2,6,6-四甲基哌啶基-1-氧基（TEMPO）淬灭的机理研究表明，酰胺基是关键的反应中间体，Fe
• Iron-Catalyzed N-Alkylation of Azoles via Cleavage of an sp³ C–H Bond Adjacent to a Nitrogen Atom
  作者：Qinqin Xia、Wanzhi Chen

  DOI：10.1021/jo301568e

  日期：2012.10.19

  Iron-catalyzed direct C-N bond formation between azoles and amides is described. The oxidative coupling reactions of sp(3) C-H bonds adjacent to a nitrogen atom in amides and sulfonamides with the N-H bond in azoles proceeded smoothly in the presence of FeCl2 and di-tert-butyl peroxide (DTBP).