1-(1-(4-fluorophenyl)vinyl)-1H-benzo[d][1,2,3]triazole | 1186338-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1-(1-(4-fluorophenyl)vinyl)-1H-benzo[d][1,2,3]triazole
• 英文别名: 1-[1-(4-Fluorophenyl)ethenyl]benzotriazole
• CAS: 1186338-75-9
• 化学式: C₁₄H₁₀FN₃
• 分子量: 239.252
• InChiKey: WKRXLYBDPOKCJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-(4-fluorophenyl)vinyl)-1H-benzo[d][1,2,3]triazole 在 碘苯二乙酸 、 叠氮基三甲基硅烷 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以76%的产率得到2-(4-fluorophenyl)quinoxaline
  参考文献：
  名称：

  Ambient Benzotriazole Ring Opening through Intermolecular Radical Addition to Vinyltriazole

  摘要：

  Radical addition to vinyltriazole was developed as a new approach to achieve 1,2,3-triazole ring opening under mild conditions. Through reagent control, excellent chemoselectivity was achieved, giving either nitrile under basic conditions or quinoxaline under neutral conditions. Reactivities made this method an attractive new reaction mode.

  DOI：

  10.1021/acs.orglett.5b00156
• 作为产物：
  描述：

  1-(1-phenylvinyl)-1H-benzo[d][1,2,3]triazole 在 ammonium cerium (IV) nitrate 、 三苯基膦氯金 、 silver trifluoromethanesulfonate 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 12.33h， 生成 1-(1-(4-fluorophenyl)vinyl)-1H-benzo[d][1,2,3]triazole
  参考文献：
  名称：

  Ambient Benzotriazole Ring Opening through Intermolecular Radical Addition to Vinyltriazole

  摘要：

  Radical addition to vinyltriazole was developed as a new approach to achieve 1,2,3-triazole ring opening under mild conditions. Through reagent control, excellent chemoselectivity was achieved, giving either nitrile under basic conditions or quinoxaline under neutral conditions. Reactivities made this method an attractive new reaction mode.

  DOI：

  10.1021/acs.orglett.5b00156

文献信息

• An organoselenium-catalyzed N¹- and N²-selective aza-Wacker reaction of alkenes with benzotriazoles
  作者：Xin Wang、Qinlin Wang、Yanru Xue、Kai Sun、Lanlan Wu、Bing Zhang

  DOI：10.1039/d0cc01079k

  日期：——

  An organoselenium-catalyzed N1- and N2-selective aza-Wacker reaction of alkenes with benzotriazoles is reported, which provides easy access to N1- and N2-olefinated benzotriazole derivatives. The wide substrate scope, good functional group tolerance, and facile scale-up of this method are expected to promote its potential application in synthetic chemistry. A preliminary mechanism is proposed to explain

  据报道烯烃与苯并三唑的有机硒催化的N1-和N2-选择性氮杂-Wacker反应，可轻松获得N1-和N2-烯化的苯并三唑衍生物。该方法的广泛底物范围，良好的官能团耐受性和简便的放大规模有望促进其在合成化学中的潜在应用。提出了一种初步的机制来解释N1和N2的选择性。
• Visible Light-Promoted Radical-Mediated Ring-Opening/Cyclization of Vinyl Benzotriazoles: An Alternative Approach to Phenanthridines
  作者：Jiaqi Li、Shichong Wang、Jingjing Zhao、Pan Li

  DOI：10.1021/acs.orglett.2c02249

  日期：2022.8.19

  tion of vinyl benzotriazoles has been developed. The method provides an efficient and practical approach to synthesize functionalized phenanthridines from vinyl benzotriazoles with alkyl bromides under mild conditions. Significantly, the readily available and bench-stable vinyl benzotriazoles can serve as valuable alternative radical acceptors during the synthesis of phenanthridines.

  已经开发了一种可见光促进的自由基介导的乙烯基苯并三唑的开环/环化。该方法为在温和条件下由乙烯基苯并三唑与烷基溴合成官能化菲啶提供了一种有效且实用的方法。重要的是，在菲啶的合成过程中，容易获得且工作稳定的乙烯基苯并三唑可以作为有价值的替代自由基受体。
• 可见光催化下烯基苯并三唑开环环化构建啡啶类化合物的合成方法
  申请人：河南大学

  公开号：CN114874141A

  公开（公告）日：2022-08-09

  本发明属于化合物制备技术领域，具体涉及可见光催化下烯基苯并三唑开环环化构建啡啶类化合物的合成方法，该方法是以式I所示的烯基苯并三唑和式II所示的叔烷基溴为原料，在碱和溶剂作用下，在室温和惰性气氛、光照条件下发生环化反应合成式III所示的啡啶类化合物。本发明中烯基苯并三唑的原料来源广泛，价格低，而且稳定性好，可长期保存，且整个反应在光照条件下进行，不需要加热，绿色环保。
• Highly efficient synthesis of vinyl substituted triazoles by Au(I) catalyzed alkyne activation
  作者：Haifeng Duan、Wuming Yan、Sujata Sengupta、Xiaodong Shi

  DOI：10.1016/j.bmcl.2009.03.096

  日期：2009.7

  Au(I) catalyzed 1,2,3-triazole addition to non-activated alkyne was reported. A large group of substituted NH-1,2,3-triazoles were suitable for this transformation along with both internal and terminal alkynes. The N-1 and N-2 vinyl substituted 1,2,3-triazoles were prepared in up to 98% yield with as low as 0.2% catalyst loading, thereby providing a new protocol for the synthesis of potentially biological-active vinyl-triazole building blocks. (C) 2009 Elsevier Ltd. All rights reserved.
• Ambient Benzotriazole Ring Opening through Intermolecular Radical Addition to Vinyltriazole
  作者：Yijin Su、Jeffrey L. Petersen、Tesia L. Gregg、Xiaodong Shi

  DOI：10.1021/acs.orglett.5b00156

  日期：2015.3.6

  Radical addition to vinyltriazole was developed as a new approach to achieve 1,2,3-triazole ring opening under mild conditions. Through reagent control, excellent chemoselectivity was achieved, giving either nitrile under basic conditions or quinoxaline under neutral conditions. Reactivities made this method an attractive new reaction mode.