N-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)acetamide | 215942-71-5

• 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)acetamide
• 英文别名: N-(1H-1,2,3-Benzotriazol-1-ylmethyl)acetamide；N-(benzotriazol-1-ylmethyl)acetamide
• CAS: 215942-71-5
• 化学式: C₉H₁₀N₄O
• 分子量: 190.205
• InChiKey: HKSKZFRZPZVRCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  465.5±28.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(1H-1,2,3-苯并噻唑-1-基)乙酮 在 盐酸羟胺 作用下， 以 溶剂黄146 为溶剂， 反应 0.33h， 以68%的产率得到N-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)acetamide
  参考文献：
  名称：

  功能取代的烷基苯并三唑：烷基苯并三唑对亲电和亲核试剂的反应性

  摘要：

  报道了苯并三唑基丙酮对各种碳和氮亲电试剂的反应性。已经合成了几种新型唑基苯并三唑以及苯并三唑基-肉啉。© 2002 Wiley Periodicals, Inc. 杂原子化学 13:141–145, 2002; 在线发表于 Wiley Interscience (www.interscience.wiley.com)。DOI 10.1002/hc.10009

  DOI：

  10.1002/hc.10009

文献信息

• 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
• Cycloaddition of Heteroatom-Substituted 2-Azaallyl Anions with Alkenes. Synthesis of 1-Pyrrolines and Bridged Azabicyclic Compounds
  作者：William H. Pearson、Erland P. Stevens

  DOI：10.1021/jo981457i

  日期：1998.12.1

  Nonstabilized 2-azaallyl anions bearing heteroatom substituents [(RCHNC)-C-1(X)R-2(-)Li(+), where R-1 and R-2 are hydrogen or alkyl groups and X = OMe, SPh, or NR2] were generated and found to undergo efficient [3 + 2] cycloadditions with alkenes to provide 1-pyrrolines after loss of LiX. The 2-azaallyl anions were generated by tin-lithium exchange on stannyl imidates, thioimidates, or amidines (RCH)-C-1(SnBu3)N=C(X)R-2 with n-butyllithium. The initially formed 1-pyrrolines were found to be deprotonated under the reaction conditions to afford 1-metalloenamines, which could be quenched with alkyl halides, carbonyl compounds, or MeSSMe to provide further functionalized 1-pyrrolines. Cyclic methoxy-substituted 2-azaallyl anions were generated and were found to undergo cycloadditions with alkenes to afford bridged azabicyclic compounds (1-methoxy-7-azabicyclo[2.2.1]heptanes and 1-methoxy-8-azabicyclo[3.2.1]octanes). These are the first examples of cyclic nonstabilized 2-azaallyl anions.