N-Allenylimidazole | 19017-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-Allenylimidazole
• 英文别名: 1H-Imidazole, 1-(1,2-propadienyl)-
• CAS: 19017-03-9
• 化学式: C₆H₆N₂
• 分子量: 106.127
• InChiKey: CQSOHHRXGYVKQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-Allenylimidazole 、 四氯化锡 以 乙醚 、 乙醇 为溶剂， 以55%的产率得到[Sn(1-allenylimidazole)2Cl4]
  参考文献：
  名称：

  摘要：

  Monomeric complexes MLnXm, where M = Co2+, Ni2+, Zn2+, Cd2+, Cu2+, Pd2+, Sn4+; L = 1-allenylimidazole, 1-allenyl-2-methylimidazole, 1-allenylbenzimidazole; n = 2, 4; m = 1, 2, 4; X = Cl, OCOCH3, was prepared for the first time, and their structure was studied by NMR and IR spectroscopy. In the complexes, 1-allenylimidazoles act as monodentate ligands, coordinating via the heteroring N-3 atom, and the CH2=C=CH group is stabilized by coordination of the azolyl ring with the metal, which hinders electron transfer from the heteroring to the allenyl fragment. The prospective use of the complexes of Zn(OCOCH3)(2) with 1-allenyl imidazole derivatives as antidotes and antihypoxants was demonstrated.

  DOI：

  10.1023/a:1020808703299
• 作为产物：
  描述：

  N-炔丙基咪唑 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以52%的产率得到N-Allenylimidazole
  参考文献：
  名称：

  Broggini, Gianluigi; Bruche, Luca; Zecchi, Gaetano, Journal of the Chemical Society. Perkin transactions I, 1990, p. 533 - 539

  摘要：

  DOI：

文献信息

• Copper-Catalyzed Hydroamination of <i>N</i> -Allenylazoles: Access to Amino-Substituted <i>N</i> -Vinylazoles
  作者：Luca Alessandro Perego、Rémi Blieck、Julie Michel、Ilaria Ciofini、Laurence Grimaud、Marc Taillefer、Florian Monnier

  DOI：10.1002/adsc.201700965

  日期：2017.12.19

  and simple procedure for the hydroamination of N‐allenylazoles with secondary amines. The reaction proceeds under mild conditions by copper(I) catalysis yielding the corresponding original linear E allylic amines with total regio‐ and stereoselectivity. Density Functional Theory (DFT) calculations offer a mechanistic explanation of the significantly higher reactivity of N‐allenyl‐(1,2)‐azoles compared

  在机理研究的基础上，已利用吡咯类化合物作为引导基团的先天能力来设计一种有效而简单的程序，用于将N-烯丙基唑类化合物与仲胺进行加氢胺化。在铜（I）催化下，反应在温和条件下进行，得到相应的原始线性E烯丙基胺，具有总的区域和立体选择性。密度泛函理论（DFT）计算提供了一种机械解释，表明N-烯丙基-（1,2）-吡咯的反应活性明显高于其1,3-类似物，这是由于类似吡啶的反应增强了配位作用氮到达铜中心。
• Selective N-prop-2-ynylation of heterocycles induced by solid–liquid phase transfer catalysis without solvent and use of solid inorganic supports
  作者：Hervé Galons、Isabelle Bergerat、Claude Combet-Farnoux、Marcel Miocque、Guy Decodts、Georges Bram

  DOI：10.1039/c39850001730

  日期：——

  Complementary processes promote the N-prop-2-ynylation of heterocycles: solid-liquid phase transfer catalysis without added solvent in the presence or absence of alumina or titanium dioxide and alkylation on ‘basic’ alumina in ‘dry media’.

  互补过程促进杂环的N -prop-2-yylation：在存在或不存在氧化铝或二氧化钛的情况下，不添加溶剂的固-液相转移催化，以及在“干介质”中在“碱性”氧化铝上进行烷基化。
• A simple one-pot preparation of N-allenyl amides, ureas, carbamates and sulfonamides using a DMSO/tBuOK protocol
  作者：Thomas W. Bousfield、Marc C. Kimber

  DOI：10.1016/j.tetlet.2014.11.093

  日期：2015.1

  A one-pot transformation of amides, ureas, carbamates and sulfonamides into synthetically useful N-allenyl analogues using a (BuOK)-Bu-t/DMSO protocol is reported. The procedure is experimentally simple and robust, and provides N-allenyl analogues, commonly used within the literature, in yields comparable to the benchmark two-step approach. (C) 2014 Elsevier Ltd. All rights reserved.
• Tarasova; Shmidt; Klyba, Russian Journal of Organic Chemistry, 1998, vol. 34, # 5, p. 688 - 692
  作者：Tarasova、Shmidt、Klyba、Sinegovskaya、Mikhaleva、Krivdin、Trofimov

  DOI：——

  日期：——
• Synthesis ofN-allenylazoles from azoles and propargyl chloride or 1,2,3-trichloropropane in one preparative step
  作者：O. A. Tarasova、E. Yu. Shmidt、L. V. Baikalova、A. I. Mikhaleva、B. A. Trofimov

  DOI：10.1007/bf02503782

  日期：1997.11

  Reactions of imidazole and 1,2,4-triazole with propargyl chloride and its more accessible equivalent, 1,2,3-trichloropropane, in the superbasic KOH-DMSO system have been studied. The reactions afford the corresponding N-allenylazoles in one preparative step.

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