4-(1-methylethenyl)-1H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(1-methylethenyl)-1H-1,2,3-triazole
• 英文别名: 4-(α-methyl)vinyl-1H-1,2,3-triazole；4-prop-1-en-2-yl-2H-triazole
• 化学式: C₅H₇N₃
• 分子量: 109.131
• InChiKey: QREHIYFZJXSYHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基-1-丁烯-3-炔 在 sodium azide 、 copper(l) chloride 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 48.0h， 以75%的产率得到4-(1-methylethenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  亚铜介导末端炔烃与叠氮化钠环加成制备1H-1,2,3-三唑

  摘要：

  末端炔烃与叠氮化钠在氯化亚铜存在下，在高于 70 ℃的温度下反应，可以高收率地制备 1H-1,2,3-三唑。炔烃是未活化的，反应必须在惰性气体下进行。在室温下，反应首先产生 Cu(I)-叠氮化物配合物，当温度升至高于 70 °C 时，该配合物转化为 Cu-炔烃配合物。Cu(I)-炔烃配合物和叠氮化物离子从Cu(I)解离或配位到Cu(I)的反应然后得到1H-1,2,3-三唑。

  DOI：

  10.1002/jccs.200800061

文献信息

• Copper-Catalyzed Synthesis ofN-Unsubstituted 1,2,3-Triazoles from Nonactivated Terminal Alkynes
  作者：Tienan Jin、Shin Kamijo、Yoshinori Yamamoto

  DOI：10.1002/ejoc.200400442

  日期：2004.9

  The [3+2] cycloaddition of nonactivated terminal alkynes and trimethylsilyl azide proceeded smoothly in the presence of CuI catalyst and DMF/MeOH, to give the corresponding N-unsubstituted triazoles in good to high yields. The reaction most probably proceeds through the in situ formation of a copper acetylide species and hydrazoic acid, followed by a successive [3+2] cycloaddition reaction. (© Wiley-VCH

  在 CuI 催化剂和 DMF/MeOH 存在下，未活化的末端炔烃和三甲基甲硅烷基叠氮化物的 [3+2] 环加成反应顺利进行，得到相应的 N-未取代的三唑，收率良好至高。该反应很可能是通过原位形成乙炔铜物质和肼酸，然后进行连续的 [3+2] 环加成反应来进行的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Improving the Performances of Poly(vinylphosphonic acid) by Compositing or Copolymerization with Poly(4-(α-methyl)vinyl-1H-1,2,3-triazole)
  作者：Shuaiyuan Han、Baohua Yue、Liuming Yan

  DOI：10.1016/j.electacta.2014.06.121

  日期：2014.8

  The poly(vinylphosphonic acid) (PVPA), poly(4-(alpha-methypvinyl-1H-1,2,3-triazole) (PMVTri), and poly(VPA-co-MVTri) were synthesized, and proton exchange membranes were prepared based on the acid-base polymeric composite of PVPA and PMVTri, and acid-base amphoteric copolymer of poly(VPA-co-MVTri). The overall performances of PVPA, proton conductivity, thermal and oxidative stability, and water resistance, are greatly improved by compositing of PMVTri or copolymerization with 4-(alpha-methyl)vinyl-1H-1,2,3-triazole (MVTri). About four or eight folds improvement in maximum proton conductivity was observed in the polymeric composite of PVPA/PMVTri or acid-base amphoteric copolymer poly(VPA-co-MVTri) because of the redistribution of ions in the heterostructures of PVPA and PMVTri, respectively, compared with the pristine PVPA. At the same time, the oxidative stability and the water resistance of PVPA were also greatly improved attributing to the absent of alpha-H in the main chain of PMVTri and the acid-base interaction between the phosphonic acid groups and the triazolyl groups, respectively. (C) 2014 Elsevier Ltd. All rights reserved.
• Preparation of 1H-1,2,3-Triazoles by Cuprous Ion Mediated Cycloaddition of Terminal Alkyne and Sodium Azide
  作者：Li-Hui Lu、Jia-Hao Wu、Chia-Hsi Yang

  DOI：10.1002/jccs.200800061

  日期：2008.4

  1H-1,2,3-triazoles can be prepared in good yield by the reaction of terminal alkyne and sodium azide in the presence of cuprous chloride at a temperature higher than 70 °C. The alkyne is unactivated and the reaction has to be carried out under inert gas. At room temperature, the reaction first gives a Cu(I)-azide complex which is converted to a Cu-alkyne complex when the temperature is raised to higher

  末端炔烃与叠氮化钠在氯化亚铜存在下，在高于 70 ℃的温度下反应，可以高收率地制备 1H-1,2,3-三唑。炔烃是未活化的，反应必须在惰性气体下进行。在室温下，反应首先产生 Cu(I)-叠氮化物配合物，当温度升至高于 70 °C 时，该配合物转化为 Cu-炔烃配合物。Cu(I)-炔烃配合物和叠氮化物离子从Cu(I)解离或配位到Cu(I)的反应然后得到1H-1,2,3-三唑。