Methyl 3-(4-Azido-2,3,5,6-tetrafluorobenzamido)-5-iodobenzoate | 138724-27-3

• 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: Methyl 3-(4-Azido-2,3,5,6-tetrafluorobenzamido)-5-iodobenzoate
• 英文别名: Methyl 3-[(4-azido-2,3,5,6-tetrafluorobenzoyl)amino]-5-iodobenzoate
• CAS: 138724-27-3
• 化学式: C₁₅H₇F₄IN₄O₃
• 分子量: 494.144
• InChiKey: HUXJFPYUNVOSSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69.8
• 氢给体数：
  1
• 氢受体数：
  9

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	Methyl 3-(4-Azido-2,3,5,6-tetrafluorobenzamido)-5-aminobenzoate	138724-23-9	C15H9F4N5O3	383.262
  4-叠氮基-2,3,5,6-四氟苯甲酸	4-azido-2,3,5,6-tetrafluorobenzoic acid	122590-77-6	C7HF4N3O2	235.097

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3-[4-(N',N'-Diethyl-hydrazino)-2,3,5,6-tetrafluoro-benzoylamino]-5-iodo-benzoic acid methyl ester	138753-42-1	C19H18F4IN3O3	539.268
  ——	Methyl 3-(4-Amino-2,3,5,6-tetrafluorobenzamido)benzoate	138724-37-5	C15H10F4N2O3	342.25
  ——	3-[4-(N',N'-Diethyl-hydrazino)-2,3,5,6-tetrafluoro-benzoylamino]-benzoic acid methyl ester	138753-43-2	C19H19F4N3O3	413.372

反应信息

• 作为反应物：
  描述：

  Methyl 3-(4-Azido-2,3,5,6-tetrafluorobenzamido)-5-iodobenzoate 在 二乙胺 作用下， 以 环己烷 为溶剂， 反应 2.0h， 以22%的产率得到3-(4-Amino-2,3,5,6-tetrafluoro-benzoylamino)-5-iodo-benzoic acid methyl ester
  参考文献：
  名称：

  Toward the development of radiolabeled fluorophenyl azide-based photolabeling reagents: synthesis and photolysis of iodinated 4-azidoperfluorobenzoates and 4-azido-3,5,6-trifluorobenzoates

  摘要：

  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.

  DOI：

  10.1021/jo00030a046
• 作为产物：
  描述：

  4-叠氮基-2,3,5,6-四氟苯甲酸 在 盐酸 、 N,N'-二环己基碳二亚胺 、 sodium iodide 、 sodium nitrite 作用下， 以 氯仿 为溶剂， 反应 16.5h， 生成 Methyl 3-(4-Azido-2,3,5,6-tetrafluorobenzamido)-5-iodobenzoate
  参考文献：
  名称：

  Toward the development of radiolabeled fluorophenyl azide-based photolabeling reagents: synthesis and photolysis of iodinated 4-azidoperfluorobenzoates and 4-azido-3,5,6-trifluorobenzoates

  摘要：

  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.

  DOI：

  10.1021/jo00030a046

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.