4-(4-methylphenyl)-1-phenylbut-3-yn-1-yl azide | 1132645-43-2

• 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: 4-(4-methylphenyl)-1-phenylbut-3-yn-1-yl azide
• 英文别名: 1-(4-Azido-4-phenylbut-1-ynyl)-4-methylbenzene；1-(4-azido-4-phenylbut-1-ynyl)-4-methylbenzene
• CAS: 1132645-43-2
• 化学式: C₁₇H₁₅N₃
• 分子量: 261.326
• InChiKey: SSGGBOJKCAWMAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-methylphenyl)-1-phenylbut-3-yn-1-yl azide 在 zinc(II) chloride 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 105.0 ℃ 、200.0 kPa 条件下， 反应 1.0h， 以90%的产率得到2-phenyl-5-(p-tolyl)-1H-pyrrole
  参考文献：
  名称：

  Microwave-assisted zinc chloride-catalyzed synthesis of substituted pyrroles from homopropargyl azides

  摘要：

  Ligand-free 5-endo-dig cyclization of 1,4- and 1,2,4-substituted but-3-yn-1-yl (homopropargyl) azides in the presence of zinc chloride (usually 20 mol %) in dichloroethane at elevated temperature provides 2,5-di- and 2,3,5-trisubstituted pyrroles in high to moderate yields (91-41%). Both conventional and microwave protocols furnished comparable results. A structure of 2-(4-fluorophenyl)-5-(4-methyl-phenyl)-1H-pyrrole was confirmed by X-ray crystallography. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.094
• 作为产物：
  描述：

  1-phenyl-4-(p-tolyl)but-3-yn-1-ol 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 二苯基膦叠氮化物 作用下， 以 四氢呋喃 为溶剂， 反应 12.17h， 生成 4-(4-methylphenyl)-1-phenylbut-3-yn-1-yl azide
  参考文献：
  名称：

  3,4-双硫醇化吡咯：简明结构及其电子特性

  摘要：

  3,4-二硫代吡咯构成了吡咯基半导体的关键核心，二硫基可以通过S效应改善其电子性能。在此，通过AlCl 3催化的同炔丙基叠氮化物的硫醇化/环化，开发了一种合成3,4-二硫醇化吡咯的简便方法，循环伏安法和DFT计算表明，所需的3,4-二硫醇化吡咯具有更高的HOMO轨道能量和比母体未取代的 2,5-二苯基吡咯更低的带隙。

  DOI：

  10.1021/acs.joc.1c02269

文献信息

• Copper-Catalyzed Cascade Transformation of Homopropargyl Azides into Trifluoromethylated Nitriles via C–C Cleavage
  作者：Shuang Chen、Deng-Yuan Li、Liang-Liang Jiang、Kai Liu、Pei-Nian Liu

  DOI：10.1021/acs.orglett.7b00571

  日期：2017.4.21

  A cascade reaction of homopropargyl azides in the presence of a Cu catalyst was achieved, affording 3-(trifluoromethyl)but-3-enenitriles with good yields and excellent regioselectivity. This reaction appears to be the first direct conversion of homopropargyl azides into trifluoromethylated nitriles. Mechanistic studies indicate that the transformation proceeds by addition of a CF3 radical to the alkyne

  在铜催化剂的存在下，实现了高炔丙基叠氮化物的级联反应，从而以良好的收率和优异的区域选择性提供了3-（三氟甲基）丁-3-烯腈。该反应似乎是高炔丙基叠氮化物首次直接转化为三氟甲基化的腈。机理研究表明，转化过程是通过向炔烃中添加CF 3自由基，通过1,4-芳基自由基迁移进行C–C裂解以及形成腈而进行的。该协议提供了一种通过自由基迁移产生的C–C裂解将叠氮化物转化为腈的新策略。
• Alternate Mode of Palladium-Catalyzed Alkynyliminium Ion Cyclizations Affording Stereodefined <i>N</i>-Alkyl-3-alkylidenepyrrolidines
  作者：Hirokazu Tsukamoto、Mitsugu Shiraishi、Takayuki Doi

  DOI：10.1021/ol402685g

  日期：2013.12.6

  Pd/P(c-C6H11)(3)-catalyzed alkynyliminium ion cyclization in the presence of organoboronic acids affords stereodefined N-alkyl-3-alkylidenepyrrolidines. The distinctive cis-selective addition of the boronic acids and the iminium ions across the alkyne would result from favored 5-exo- or 6-exo-dig cyclization through oxidative addition of the formaldiminium ions to Pd(0).
• 3,4-Bisthiolated Pyrroles: Concise Construction and Their Electronic Properties
  作者：Jun Tian、Kai Feng、Kang-Ning Yuan、Xing Li、Hong-Hong Chang、Wen-Chao Gao

  DOI：10.1021/acs.joc.1c02269

  日期：2022.3.4

  3,4-Bisthiolated pyrroles constitute key cores in pyrrole-based semiconductors, and their electronic properties could be improved by the bisthio groups via the S-effect. Herein, a convenient method for the synthesis of 3,4-bisthiolated pyrroles has been developed through the AlCl3-catalyzed thiolation/cyclization of homopropargylic azides, and cyclic voltammetry and DFT calculations indicated that

  3,4-二硫代吡咯构成了吡咯基半导体的关键核心，二硫基可以通过S效应改善其电子性能。在此，通过AlCl 3催化的同炔丙基叠氮化物的硫醇化/环化，开发了一种合成3,4-二硫醇化吡咯的简便方法，循环伏安法和DFT计算表明，所需的3,4-二硫醇化吡咯具有更高的HOMO轨道能量和比母体未取代的 2,5-二苯基吡咯更低的带隙。
• Microwave-assisted zinc chloride-catalyzed synthesis of substituted pyrroles from homopropargyl azides
  作者：Przemysław Wyrębek、Adam Sniady、Nicholas Bewick、Yan Li、Agnieszka Mikus、Kraig A. Wheeler、Roman Dembinski

  DOI：10.1016/j.tet.2008.11.094

  日期：2009.2

  Ligand-free 5-endo-dig cyclization of 1,4- and 1,2,4-substituted but-3-yn-1-yl (homopropargyl) azides in the presence of zinc chloride (usually 20 mol %) in dichloroethane at elevated temperature provides 2,5-di- and 2,3,5-trisubstituted pyrroles in high to moderate yields (91-41%). Both conventional and microwave protocols furnished comparable results. A structure of 2-(4-fluorophenyl)-5-(4-methyl-phenyl)-1H-pyrrole was confirmed by X-ray crystallography. (C) 2008 Elsevier Ltd. All rights reserved.