1-benzyl-4-butyl-5-(phenylselanyl)-1H-1,2,3-triazole | 1605324-44-4

• 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: 1-benzyl-4-butyl-5-(phenylselanyl)-1H-1,2,3-triazole
• 英文别名: 1-Benzyl-4-butyl-5-phenylselanyltriazole；1-benzyl-4-butyl-5-phenylselanyltriazole
• CAS: 1605324-44-4
• 化学式: C₁₉H₂₁N₃Se
• 分子量: 370.356
• InChiKey: VZGRTYMVQWRODC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  溴甲苯 在 sodium azide 、 1,10-菲罗啉 、 copper(II) acetate monohydrate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 1-benzyl-4-butyl-5-(phenylselanyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Copper-Catalyzed Decarboxylative/Click Cascade Reaction: Regioselective Assembly of 5-Selenotriazole Anticancer Agents

  摘要：

  A simple and efficient Cu-catalyzed decarboxylative/click reaction for the preparation of 1,4-disubstituted 5-arylselanyl-1,2,3-triazoles from propiolic acids, diselenides, and azides has been developed. The mechanistic study revealed that the intermolecular AAC reaction of an alkynyl selenium intermediate occurred. The resulting multisubstituted 5-seleno-1,2,3-triazoles were tested for in vitro anticancer activity by MTT assay, and compounds 4f, 4h, and 4p showed potent cancer cell-growth inhibition activities.

  DOI：

  10.1021/acs.orglett.7b03734

文献信息

• Synthesis of Fully Functionalized 5-Selanyl-1,2,3-triazoles: Copper-Catalysed Three-Component Reaction of Ethynylstibanes, Organic Azides, and Diaryl Diselenides
  作者：Mizuki Yamada、Mio Matsumura、Fumina Takino、Yuki Murata、Yuka Kurata、Masatoshi Kawahata、Kentaro Yamaguchi、Naoki Kakusawa、Shuji Yasuike

  DOI：10.1002/ejoc.201701389

  日期：2018.1.17

  A Cu‐catalysed three‐component reaction of ethynylstibanes, organic azides, and diaryl diselenides under aerobic conditions leads to the formation of fully substituted 5‐selanyl‐1,2,3‐triazoles in moderate to excellent yields. Ethynylstibanes, containing an antimony atom, gave better results than various alkynes containing other typical elements, such as silicon, tin, and tellurium.

  在有氧条件下，铜催化的乙炔基乙炔类，有机叠氮化物和二芳基二硒化物的三组分反应导致完全取代的5-癸二烯丙基1,2,3-三唑的形成，产率中等至优异。与含有其他典型元素（例如硅，锡和碲）的各种炔烃相比，含有锑原子的乙炔基斯蒂班尼类化合物的结果更好。
• Iridium-Catalyzed Intermolecular Azide-Alkyne Cycloaddition of Internal Thioalkynes under Mild Conditions
  作者：Shengtao Ding、Guochen Jia、Jianwei Sun

  DOI：10.1002/anie.201309855

  日期：2014.2.10

  An iridium‐catalyzed azide–alkyne cycloaddition reaction (IrAAC) of electron‐rich internal alkynes is described. It is the first efficient intermolecular AAC of internal thioalkynes. The reaction exhibits remarkable features, such as high efficiency and regioselectivity, mild reaction conditions, easy operation, and excellent compatibility with air and a broad spectrum of organic and aqueous solvents

  描述了富电子内部炔烃的铱催化的叠氮化物-炔烃环加成反应（IrAAC）。它是内部硫代炔烃的第一种有效的分子间AAC。该反应显示出显着的特征，例如高效和区域选择性，温和的反应条件，易于操作以及与空气和广泛的有机和水性溶剂的优异相容性。它是对著名的CuAAC和RuAAC点击反应的补充。
• Copper-Catalyzed Decarboxylative/Click Cascade Reaction: Regioselective Assembly of 5-Selenotriazole Anticancer Agents
  作者：Fei-hu Cui、Jing Chen、Zu-yu Mo、Shi-xia Su、Yan-yan Chen、Xian-li Ma、Hai-tao Tang、Heng-shan Wang、Ying-ming Pan、Yan-li Xu

  DOI：10.1021/acs.orglett.7b03734

  日期：2018.2.16

  A simple and efficient Cu-catalyzed decarboxylative/click reaction for the preparation of 1,4-disubstituted 5-arylselanyl-1,2,3-triazoles from propiolic acids, diselenides, and azides has been developed. The mechanistic study revealed that the intermolecular AAC reaction of an alkynyl selenium intermediate occurred. The resulting multisubstituted 5-seleno-1,2,3-triazoles were tested for in vitro anticancer activity by MTT assay, and compounds 4f, 4h, and 4p showed potent cancer cell-growth inhibition activities.