(E)-1-(3-fluorostyryl)-1H-imidazole | 1233718-80-3

• 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: (E)-1-(3-fluorostyryl)-1H-imidazole
• 英文别名: 1-[(E)-2-(3-fluorophenyl)ethenyl]imidazole
• CAS: 1233718-80-3
• 化学式: C₁₁H₉FN₂
• 分子量: 188.204
• InChiKey: KFZACDTYEOTMQG-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  咪唑 、 1-乙炔基-3-氟苯 在 cesiumhydroxide monohydrate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 以44%的产率得到(E)-1-(3-fluorostyryl)-1H-imidazole
  参考文献：
  名称：

  Inorganic base-mediated stereoselective hydroamination of arylalkynes with imidazole: An efficient access to N -vinylimidazoles

  摘要：

  A metal-free inorganic base-mediated highly stereoselective hydroamination of arylalkynes with imidazoles has been developed, and the corresponding N-vinylimidazoles were obtained in good yields and with moderate to excellent stereoselectivities (up to 99:1). For the electron rich alkynes, the reaction system of CsOH center dot H2O/NMP/140 degrees C led to the predominant formation of E-addition products, while the reaction system of KOH/NMP/90 degrees C afforded the Z-isomers as the major product. The electron deficient alkynes furnished predominantly the E-addition products in both reaction systems. This study essentially provides a general and an efficient protocol for the synthesis of E-isomer of the N-vinylimidazoles. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.07.022

文献信息

• Copper oxide nanoparticles catalyzed vinylation of imidazoles with vinyl halides under ligand-free conditions
  作者：V. Prakash Reddy、A. Vijay Kumar、K. Rama Rao

  DOI：10.1016/j.tetlet.2010.04.022

  日期：2010.6

  Recyclable copper oxide nanoparticles catalyzed most efficient and straightforward protocol for the vinylation of imidazoles with vinyl halides under ligand-free conditions. Utilizing this protocol various imidazoles were cross-coupled with different substituted vinyl halides to get the corresponding products in excellent yields with the retention configuration. (C) 2010 Elsevier Ltd. All rights reserved.
• Inorganic base-mediated stereoselective hydroamination of arylalkynes with imidazole: An efficient access to N -vinylimidazoles
  作者：Lin-Dong Liu、Zhong-Liang Lei、Hong Wang、Ming Bian、Zhen-Jiang Liu、Jin-Tao Liu、Xiao-Jun Hu

  DOI：10.1016/j.tet.2018.07.022

  日期：2018.8

  A metal-free inorganic base-mediated highly stereoselective hydroamination of arylalkynes with imidazoles has been developed, and the corresponding N-vinylimidazoles were obtained in good yields and with moderate to excellent stereoselectivities (up to 99:1). For the electron rich alkynes, the reaction system of CsOH center dot H2O/NMP/140 degrees C led to the predominant formation of E-addition products, while the reaction system of KOH/NMP/90 degrees C afforded the Z-isomers as the major product. The electron deficient alkynes furnished predominantly the E-addition products in both reaction systems. This study essentially provides a general and an efficient protocol for the synthesis of E-isomer of the N-vinylimidazoles. (C) 2018 Elsevier Ltd. All rights reserved.