4-azido-2-iodo-3,5,6-trifluorobenzoate | 126695-70-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4-azido-2-iodo-3,5,6-trifluorobenzoate
• 英文别名: Methyl 4-Azido-2-iodo-3,5,6-trifluorobenzoate；Methyl 4-azido-2,3,5-trifluoro-6-iodobenzoate
• CAS: 126695-70-3
• 化学式: C₈H₃F₃IN₃O₂
• 分子量: 357.03
• InChiKey: JISOQSAXJIJVHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-azido-2-iodo-3,5,6-trifluorobenzoate 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.0h， 生成 N-Succinimidyl 4-Azido-2-iodo-3,5,6-trifluorobenzoate
  参考文献：
  名称：

  4-叠氮基-2-碘代-3,5,6-三氟苯基羰基衍生物。新型功能化和碘化全氟苯基叠氮化物光敏标签

  摘要：

  合成了碘化全氟苯基叠氮化物4和NHS酯7。叠氮化物4在DEA /环己烷中的光解得到NH插入产物9（24％）。为了光标记的目的，这构成了对非氟化类似物行为的显着改善。

  DOI：

  10.1016/s0040-4039(01)80580-3
• 作为产物：
  描述：

  methyl 2-amino-4-azido-3,5,6-trifluorobenzoate 在 硫酸 、 水 、 sodium nitrite 作用下， 以 硫酸 、 溶剂黄146 为溶剂， 反应 1.5h， 生成 4-azido-2-iodo-3,5,6-trifluorobenzoate
  参考文献：
  名称：

  4-叠氮基-2-碘代-3,5,6-三氟苯基羰基衍生物。新型功能化和碘化全氟苯基叠氮化物光敏标签

  摘要：

  合成了碘化全氟苯基叠氮化物4和NHS酯7。叠氮化物4在DEA /环己烷中的光解得到NH插入产物9（24％）。为了光标记的目的，这构成了对非氟化类似物行为的显着改善。

  DOI：

  10.1016/s0040-4039(01)80580-3

文献信息

• Toward the development of radiolabeled fluorophenyl azide-based photolabeling reagents: synthesis and photolysis of iodinated 4-azidoperfluorobenzoates and 4-azido-3,5,6-trifluorobenzoates
  作者：Sui Xiong Cai、Denis J. Glenn、John F. W. Keana

  DOI：10.1021/jo00030a046

  日期：1992.2

  Two approaches for the incorporation of iodine into functionalized perfluorophenyl azides (PFPAs) were demonstrated by the synthesis of 3, 5, and 8, with the azido and iodo groups in the same aryl ring, and 14 and 15, with the azido and iodo groups in different aryl rings. These compounds opened the way for the incorporation of radioactive iodine into PFPAs and for their attachment to other molecules as photolabels. The syntheses of trifluorophenyl azides (TFPAs) 21-23 and iodide 20 provide two possible approaches for the incorporation of a tritium atom into fluorinated photolabels. Photolysis of azide 3 in cyclohexane gave 20% of CH insertion product and in Et2NH/cyclohexane gave 24% of NH insertion product. The relatively low yield of CH and NH insertion from 3 compared with the corresponding noniodinated PFPA 24 was probably due to the heavy atom effect. Photolysis of azide 15 in Et2NH/cyclohexane gave 41% of NH insertion product. Some photodeiodination was observed both with 3 and 15. Our results demonstrate that the iodinated PFPAs studied are much better at undergoing CH and NH insertion than their nonfluorinated analogues, thus constituting an improved series of iodinated photolabeling reagents. Photolysis of TFPA 22 in cyclohexane gave 37% of CH insertion product and in Et2NH/cyclohexane gave 63% of NH insertion product, results comparable to those of PFPA 24. Thus, the desirable photochemical characteristics of the PFPAs are largely preserved in the TFPAs.