1-(2-bromophenyl)-5-phenyl-1H-1,2,3-triazole | 1246224-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-bromophenyl)-5-phenyl-1H-1,2,3-triazole
• 英文别名: 5-phenyl-1-(2-bromophenyl)-1H-1,2,3-triazole；1-(2-Bromophenyl)-5-phenyltriazole；1-(2-bromophenyl)-5-phenyltriazole
• CAS: 1246224-12-3
• 化学式: C₁₄H₁₀BrN₃
• 分子量: 300.157
• InChiKey: VBFWQUVOVPFLFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-bromophenyl)-5-phenyl-1H-1,2,3-triazole 在 palladium diacetate 、 cesium pivalate 、 三环己基膦 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以92%的产率得到[1,2,3]三唑并[1,5-F]菲啶
  参考文献：
  名称：

  通过 Pd 催化分子内苯基 C–H 活化 1,5-二芳基-1,2,3-三唑合成三唑稠合菲啶

  摘要：

  开发了一种在钯催化下由 1,5-二芳基-1,2,3-三唑合成三唑稠合菲啶的有效方法。该反应通过 Pd 催化的 1,5-二芳基-1,2,3-三唑的分子内苯基 C-H 活化进行。该方法提供了一种简洁有效的途径来以优异的产率构建三唑并 [1,5-f] 菲啶衍生物。

  DOI：

  10.1055/s-0037-1611859
• 作为产物：
  描述：

  1-叠氮基-2-溴苯 、 anti-3-phenyl-2,3-dibromopropanoic acids 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以75%的产率得到1-(2-bromophenyl)-5-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Sodium hydride-mediated synthesis of 1,5-diaryl-1,2,3-triazoles from anti-3-aryl-2,3-dibromopropanoic acids and organic azides

  摘要：

  A series of 1,5-disubstituted 1,2,3-triazoles are synthesized by a one-pot process from anti-3-aryl-2,3-dibromopropanoic acids and organic azides mediated by sodium hydride in dimethyl sulfoxide. The reaction is mild and simple, does not require a transition-metal catalyst, and gives products in good to excellent yields. (C) 2013 Chun-Xiang Kuang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.05.007

文献信息

• Transition-Metal-Free Catalytic Synthesis of 1,5-Diaryl-1,2,3-triazoles
  作者：Sen W. Kwok、Joseph R. Fotsing、Rebecca J. Fraser、Valentin O. Rodionov、Valery V. Fokin

  DOI：10.1021/ol101568d

  日期：2010.10.1

  1,5-Diarylsubstituted 1,2,3-triazoles are formed in high yield from aryl azides and terminal alkynes in DMSO in the presence of catalytic tetraalkylammonium hydroxide. The reaction is experimentally simple, does not require a transition-metal catalyst, and is not sensitive to atmospheric oxygen and moisture.
• Synthesis of Triazole-Fused Phenanthridines through Pd-Catalyzed Intramolecular Phenyl C–H Activation of 1,5-Diaryl-1,2,3-triazoles
  作者：Jiazhuang Wang、Jianhua Yang、Xuxin Fu、Guiping Qin、Tiebo Xiao、Yubo Jiang

  DOI：10.1055/s-0037-1611859

  日期：2019.7

  An efficient method for the synthesis of triazole-fused phenanthridines from 1,5-diaryl-1,2,3-triazoles under palladium catalysis has been developed. The reaction proceeds through Pd-catalyzed intramolecular phenyl C–H activation of 1,5-diaryl-1,2,3-triazoles. This method provides a concise and efficient pathway to construct triazolo[1,5-f]phenanthridine derivatives in excellent yields.

  开发了一种在钯催化下由 1,5-二芳基-1,2,3-三唑合成三唑稠合菲啶的有效方法。该反应通过 Pd 催化的 1,5-二芳基-1,2,3-三唑的分子内苯基 C-H 活化进行。该方法提供了一种简洁有效的途径来以优异的产率构建三唑并 [1,5-f] 菲啶衍生物。
• Sodium hydride-mediated synthesis of 1,5-diaryl-1,2,3-triazoles from anti-3-aryl-2,3-dibromopropanoic acids and organic azides
  作者：Xue-Zhi Cheng、Wei Liu、Zhen-Dong Huang、Chun-Xiang Kuang

  DOI：10.1016/j.cclet.2013.05.007

  日期：2013.8

  A series of 1,5-disubstituted 1,2,3-triazoles are synthesized by a one-pot process from anti-3-aryl-2,3-dibromopropanoic acids and organic azides mediated by sodium hydride in dimethyl sulfoxide. The reaction is mild and simple, does not require a transition-metal catalyst, and gives products in good to excellent yields. (C) 2013 Chun-Xiang Kuang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.