'α-o-Toluidinomethylen-acetophenon'

• 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: 'α-o-Toluidinomethylen-acetophenon'
• 英文别名: 3-o-Toluidino-acrylophenon；3-(2-Methylanilino)-1-phenylprop-2-en-1-one
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: AXGQHNHPIXRPTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  'α-o-Toluidinomethylen-acetophenon' 在 对甲苯磺酰叠氮 、 sodium t-butanolate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以63 mg的产率得到1-(2-methylphenyl)-4-phenoyl-1,2,3-triazole
  参考文献：
  名称：

  Base-Promoted Synthesis of N-Substituted 1,2,3-Triazoles via Enaminone–Azide Cycloaddition Involving Regitz Diazo Transfer

  摘要：

  The domino reactions between NH-based secondary enaminones and tosyl azide have been developed for the synthesis of various N-substituted 1,2,3-triazoles by employing t-BuONa as the base promoter. Through a key Regitz diazo-transfer process with tosyl azide, the reactions proceed efficiently at room temperature with good substrate tolerance.

  DOI：

  10.1021/acs.orglett.6b02975
• 作为产物：
  描述：

  1-phenyl-3-dimethylaminoprop-2-enone 、 邻甲苯胺 在 iron(III) chloride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 'α-o-Toluidinomethylen-acetophenon'
  参考文献：
  名称：

  Base-Promoted Synthesis of N-Substituted 1,2,3-Triazoles via Enaminone–Azide Cycloaddition Involving Regitz Diazo Transfer

  摘要：

  The domino reactions between NH-based secondary enaminones and tosyl azide have been developed for the synthesis of various N-substituted 1,2,3-triazoles by employing t-BuONa as the base promoter. Through a key Regitz diazo-transfer process with tosyl azide, the reactions proceed efficiently at room temperature with good substrate tolerance.

  DOI：

  10.1021/acs.orglett.6b02975

文献信息

• CF₃CO₂H-Catalyzed Synthesis of 3-Alkynylpyrrole Derivatives and Their Controlled Reduction
  作者：Yulei Zhao、Xuqiang Guo、Ruihua Zhang、Shuai Li、Tingting Chen、Xuejun Sun

  DOI：10.1021/acs.joc.1c02078

  日期：2021.11.5

  3-alkynylpyrrole derivatives. This mild cyclization reaction might proceed through the nucleophilic addition, intramolecular cyclization, and the subsequent elimination processes. The protocol features a broad substrate scope, good selectivity, and functional group tolerance. Notably, the advantage of this method is also highlighted by the controlled reduction to generate alkenyl- or alkylpyrrole derivatives in

  已经开发出一种使用硝基烯和烯胺酮的无过渡金属方法来获得 3-炔基吡咯衍生物。这种温和的环化反应可能通过亲核加成、分子内环化和随后的消除过程进行。该协议具有广泛的底物范围、良好的选择性和官能团耐受性。值得注意的是，该方法的优势还体现在受控还原以产生良好至极好的收率的烯基或烷基吡咯衍生物。
• Chemoselectivity of the CuAAC/Ring Cleavage/Cyclization Reaction between Enaminones and α-Acylketenimine
  作者：Guanrong Li、Danyang Luo、Qiaoli Luo、Zixin Huang、Weimin Zhuang、Hui Luo、Weiguang Yang

  DOI：10.1021/acs.joc.3c02095

  日期：2024.2.16

  synthons. However, in general, ketenimines preferentially undergoes nucleophilic addition reactions with hydroxyl and amino groups, and carbon functional groups remain a less studied subset of such systems. Herein, we develop a straightforward syntheses of pyridin-4(1H)-imines that is achieved by cyclization of a reacting enaminone unit with α-acylketenimine which is generated from the reactions of

  烯酮亚胺代表一类重要的活性物质、有用的合成中间体和合成子。然而，一般来说，烯酮亚胺优先与羟基和氨基发生亲核加成反应，而碳官能团仍然是此类系统中研究较少的子集。在此，我们开发了一种直接合成吡啶-4( 1H )-亚胺的方法，该合成是通过反应烯胺酮单元与α-酰基乙烯酮亚胺的环化来实现的，α-酰基乙烯酮亚胺是由磺酰叠氮化物和末端炔酮原位反应生成的（CuAAC/环裂解）反应）。级联过程优先从烯胺酮单元的亲核α-C而不是氨基开始，攻击烯酮亚胺的缺电子中心碳，通过分子内环化形成化学选择性非常规产物pyridin-4(1 H )-亚胺。
• Base-Promoted Synthesis of <i>N</i>-Substituted 1,2,3-Triazoles via Enaminone–Azide Cycloaddition Involving Regitz Diazo Transfer
  作者：Jie-Ping Wan、Shuo Cao、Yunyun Liu

  DOI：10.1021/acs.orglett.6b02975

  日期：2016.12.2

  The domino reactions between NH-based secondary enaminones and tosyl azide have been developed for the synthesis of various N-substituted 1,2,3-triazoles by employing t-BuONa as the base promoter. Through a key Regitz diazo-transfer process with tosyl azide, the reactions proceed efficiently at room temperature with good substrate tolerance.