2',3',4',5',6'-pentafluoro-4-dimethylaminoazobenzene | 970-15-0

• 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: 2',3',4',5',6'-pentafluoro-4-dimethylaminoazobenzene
• 英文别名: 4'-dimethylamino-2,3,4,5,6-pentafluoroazobenzene；4-(CH3)2N-PhNNC6F5；4'-Dimethylamino-2,3,4,5,6-pentafluorazobenzol；N,N-dimethyl-4-[(2,3,4,5,6-pentafluorophenyl)diazenyl]aniline
• CAS: 970-15-0
• 化学式: C₁₄H₁₀F₅N₃
• 分子量: 315.246
• InChiKey: ZPDAONWINHMRBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  28
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,1-dichloro-N-(perfluorophenyl)boranamine 在 H₂O 作用下， 生成 2',3',4',5',6'-pentafluoro-4-dimethylaminoazobenzene
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.7, 1, page 1 - 84

  摘要：

  DOI：

文献信息

• Fluorocarbon derivatives of nitrogen. Part 16 [1]. Synthesis of some unsymmetrical aromatic azo-compounds via diazotisation of fluorinated aryl- and -heteroaryl-amines in hydrofluoric or sulphuric acid [2]
  作者：Adam C. Alty、Ronald E. Banks、A.Ronald Thompson、Haralambos S. Vellis、Brian R. Fishwick

  DOI：10.1016/s0022-1139(00)83063-8

  日期：1988.8

  arenediazonium ions selected from the benzenic, pyridinic and pyrimidinic classes [ArF  C6F5, 4CF3C6F4, 4C5F4N, 4z.sbnd;C5F3N.Cl3, 4C5F2N.Cl23,5, 2C5F3N.CF(CF3)24, 4C4F3N2] and one or more aromatic compounds activated towards electrophilic attack (ArH  1,3,5,ME3C6H3, 1,3,5Et3C6H3, MeOC6H6, and napth-2-ol). The diazonium ions were generated by addition of solid sodium nitrite to solutions

  耦合类型的Ar的反应˚F Ñ + 2 + ARH→氩˚F NNAr+ H +已经从苯环，吡啶和的嘧啶类选择的氟化芳基重氮离子之间完成[氩˚F Ç 6 ˚F 5，4CF 3 ç 6 ˚F 4，4C 5 ˚F 4 N，4z.sbnd;ç 5 ˚F 3 N.Cl3，4C 5 ˚F 2 N.Cl 2 3,5，2C 5 ˚F 3 N. CF（CF 3）24，4C 4 ˚F3 Ñ 2朝向电攻击（ARH1,3,5，ME活化]和一种或多种芳族化合物3 Ç 6 ħ 3，1,3,5Et 3 Ç 6 ħ 3，MeOC 6 ħ 6，和napth-2-ol）。重氮离子是通过将亚硝酸钠固体加到胺Ar F NH 2在无水氟化氢，80％氢氟酸或98％硫酸与冰醋酸和丙酸混合而成的溶液中而生成的。这项工作已经确定，全氟化的芳族重氮离子属于其一般类别中最亲电子的物种。
• Activation of the Aryl Hydrocarbon Receptor by Methyl Yellow and Related Congeners: Structure-Activity Relationships in Halogenated Derivatives.
  作者：Taka-aki Kato、Tomonari Matsuda、Saburo Matsui、Takaharu Mizutani、Ken-ichi Saeki

  DOI：10.1248/bpb.25.466

  日期：——

  The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that mediates the biological action of many environmental compounds. Methyl yellow (4-dimethylaminoazobenzene; MY) is a principal azo-dye, and structurally related compounds were subjected to analysis of structure–activity relationships as AhR ligands by using a yeast AhR signaling assay. The effects of halogen-substitution among 23 halogenated MYs on the AhR ligand activity can be summarized as follows: enhancement by halogen-substitution at the ortho-position (2′- and 6′-position), and reduction by substitution at the para-position (4′-position). The greatest enhancement of the ligand activity was observed in 2′,6′-dichlorinated MY (13.5-fold of MY), and its AhR ligand activity was very close to that of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in the present assay system. In the study of compounds structurally related to MY, benzanilide (BA) showed almost the same AhR ligand activity as azobenzene and trans-stilbene. Furthermore, 4′-chlorobenzanilide, in which the length of the molecule is similar to that of MY, enhanced the AhR ligand activity by ortho(2′)-chlorine-substitution, and the AhR ligand activity of 2′,4′-dichlorobenzanilide was similar to that of 2′-chloro-MY. These results suggest that the amide bond is equivalent to the –N=N– or –CH=CH– double bond for recognition as the ligand by AhR in 1,2-diphenyl-1,2-ene derivatives.

  芳香烃受体(AhR)是一种配体激活的转录因子，可介导多种环境化合物的生物作用。甲基黄(4-二甲氨基偶氮苯；MY)是一种主要的偶氮染料，通过使用酵母AhR信号检测方法，对结构相关化合物进行了结构-活性关系分析，以评估其作为AhR配体的特性。 对23种卤代甲基黄的AhR配体活性的卤素取代效应可总结如下：邻位(2'和6'位)的卤素取代增强活性，对位(4'位)取代则降低活性。2',6'-二氯代甲基黄表现出最强的配体活性增强效果(是MY的13.5倍)，其AhR配体活性与2,3,7,8-四氯二苯并-p-二恶英(TCDD)在本检测系统中的活性非常接近。 在研究与MY结构相关的化合物时发现，苯甲酰苯胺(BA)显示出与偶氮苯和反式二苯乙烯几乎相同的AhR配体活性。此外，分子长度与MY相似的4'-氯代苯甲酰苯胺通过邻位(2')氯取代增强了AhR配体活性，2',4'-二氯代苯甲酰苯胺的AhR配体活性与2'-氯代-MY相似。 这些结果表明，在1,2-二苯基-1,2-烯衍生物中，酰胺键与-N=N-或-CH=CH-双键在被AhR识别为配体时具有等效作用。
• 372. Aromatic polyfluoro-compounds. Part XXI. Reactions of the pentafluorobenzenediazonium ion
  作者：G. M. Brooke、E. J. Forbes、R. D. Richardson、M. Stacey、J. C. Tatlow

  DOI：10.1039/jr9650002088

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.7, 1, page 1 - 84
  作者：

  DOI：——

  日期：——