4-Acetyl-phenyl-diazonium | 19262-73-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Acetyl-phenyl-diazonium
• 英文别名: p-Acetylbenzol-diazonium；4-Acetyl-benzol-diazonium；Benzenediazonium, 4-acetyl-；4-acetylbenzenediazonium
• CAS: 19262-73-8
• 化学式: C₈H₇N₂O
• 分子量: 147.156
• InChiKey: HOUVKCFKDQXNPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  45.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Acetyl-phenyl-diazonium 在 sodium carbonate 作用下， 生成 (4-Acetyl-phenylmercapto)-essigsaeure
  参考文献：
  名称：

  Riess; Frankfurter, Monatshefte fur Chemie, 1928, vol. 50, p. 71

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氨基苯乙酮 在 氢气 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 4-Acetyl-phenyl-diazonium
  参考文献：
  名称：

  Saran, K. B.; Roy, B. C.; Lahiri, S., Journal of the Indian Chemical Society, 1985, vol. 62, # 3, p. 181 - 183

  摘要：

  DOI：

文献信息

• The effect of <i>ortho</i> and <i>para</i> substituents on the formation of the <i>E</i> and <i>Z</i> isomers of the arylhydrazones obtained from diazonium coupling with methyl 3-aminocrotonate and 3-aminocrotononitrile
  作者：Jason V. Jollimore、Marc Vacheresse、Keith Vaughan、Donald L. Hooper

  DOI：10.1139/v96-029

  日期：1996.2.1

  Reaction of arene diazonium salts with 3-aminocrotononitrile or methyl 3-aminocrotonate affords the 2-aryl-hydrazono-3-oxobutanenitrile (1 or 3 and 3′) or the methyl 2-arylhydrazono-3-oxobutanoate (2 and 2′ or 4 and 4′). A series of these hydrazones has been prepared with a range of electron-withdrawing and -donating substituents in the ortho or para position of the aryl moiety. The hydrazones have been characterized by spectroscopic methods, with emphasis on the ¹H NMR spectra, which have been used to determine the configuration of the hydrazones as E or Z or a mixture of the two. The para-substituted hydrazononitriles (1) are formed as a single species, namely the Z isomer, whereas the ortho isomers are formed as a mixture of E and Z configurations (3 and 3′). The hydrazonobutanoates (2 and 2′ or 4 and 4′) are formed as E/Z mixtures regardless of the position of the substituent in the aryl moiety. Complete assignments of all signals in the ¹H NMR spectra have been made on the basis of the ability of the various substituents to participate in intramolecular hydrogen bonding and a mechanism is proposed to account for the variations in the proportions of E and Z isomers and the effect of the nature of the substituent on this ratio. ¹³C NMR spectra of selected hydrazones have been recorded as an aid to structure assignment. Key words: hydrazone, diazonium, NMR spectroscopy, E/Z isomers, crotonic acid derivatives.

  芳香族重氮盐与3-氨基丙烯腈或甲基3-氨基丙烯酸酯反应，得到2-芳基-叠氮基-3-氧代丁腈（1或3和3'）或甲基2-芳基叠氮基-3-氧代丁酸酯（2和2'或4和4'）。已制备了一系列这些叠氮基化合物，其中芳基部分的邻位或对位具有一系列电子吸引或供给取代基。这些叠氮基化合物已通过光谱方法进行表征，重点放在¹H NMR谱上，该谱已用于确定叠氮基的构型为E或Z或两者的混合物。对位取代的叠氮基腈（1）形成为单一种类，即Z异构体，而邻位异构体形成为E和Z构型的混合物（3和3'）。叠氮基丁酸酯（2和2'或4和4'）无论芳基部分的取代基位置如何，都形成为E/Z混合物。基于各种取代基参与分子内氢键形成的能力，已对¹H NMR谱中所有信号进行了完整的指认，并提出了一种机制来解释E和Z异构体的比例变化以及取代基性质对此比例的影响。已记录了选定叠氮基的¹³C NMR谱，以帮助结构指认。关键词：叠氮基，重氮盐，NMR光谱，E/Z异构体，丙烯酸衍生物。
• Visible Light-Driven, Gold(I)-Catalyzed Preparation of Symmetrical (Hetero)biaryls by Homocoupling of Arylazo Sulfones
  作者：Lorenzo Di Terlizzi、Simone Scaringi、Carlotta Raviola、Riccardo Pedrazzani、Marco Bandini、Maurizio Fagnoni、Stefano Protti

  DOI：10.1021/acs.joc.2c00225

  日期：2022.4.1

  The preparation of symmetrical (hetero)biaryls via arylazo sulfones has been successfully carried out upon visible light irradiation in the presence of PPh3AuCl as the catalyst. The present protocol led to the efficient synthesis of a wide range of target compounds in an organic-aqueous solvent under photocatalyst-free conditions.

  在PPh 3 AuCl作为催化剂的情况下，在可见光照射下成功地通过芳基偶氮砜制备了对称（杂）联芳基化合物。本方案可以在无光催化剂的条件下在有机水溶剂中有效合成多种目标化合物。
• Tyrosine Bioconjugation through Aqueous Ene-Like Reactions
  申请人：Barbas, III Carlos F.

  公开号：US20120289682A1

  公开（公告）日：2012-11-15

  A new and versatile class of cyclic diazodicarboxamides that reacts efficiently and selectively with phenols and the phenolic side chain of tyrosine through an Ene-like reaction is reported. This mild aqueous tyrosine ligation reaction works over a broad pH range and expands the repertoire of aqueous chemistries available for small molecule, peptide, and protein modification. The tyrosine ligation reactions are shown to be compatible with the labeling of native enzymes and antibodies in buffered aqueous solution. This reaction provides a novel synthetic approach to bispecific antibodies. This reaction will find broad utility in peptide and protein chemistry and in the chemistry of phenol-containing compounds.

  报道了一种新型多功能环状二氮基二羧酰胺类化合物，通过Ene反应与苯酚和酪氨酸的苯基侧链高效选择性反应。这种温和的水相酪氨酸连接反应适用于广泛的pH范围，并扩展了小分子、肽和蛋白质修饰的水相化学反应库。该酪氨酸连接反应可与缓冲水溶液中的天然酶和抗体标记兼容。该反应提供了一种新的双特异性抗体合成方法。该反应将在肽和蛋白质化学以及含酚化合物的化学中发挥广泛的实用价值。
• Process for the electrochemical production of a carbon-containing material whose surface is modified with organic groups, and use of the modified material
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：US20020144912A1

  公开（公告）日：2002-10-10

  Methods for producing by electrochemical reduction a carbon-containing material with its surface modified by organic groups, in particular functionalized organic groups. Certain embodiments of the methods include contacting the carbon-containing material with an organic diazonium salt in solvent, optionally in the presence of an electrolyte and negatively polarizing the carbon-containing material relative to an anode also in contact with an electrolytic solution separate from said diazonium salt solution, wherein the electrochemical reduction is carried out on an organic diazonium salt in protic solvent in an acid medium. Carbon-containing materials with a surface modified by organic groups and the use of these modified materials, for example for producing composite materials or for fixing molecules of biological interest, are taught.

  通过电化学还原生产表面被有机基团，特别是官能化有机基团修饰的含碳材料的方法。该方法的某些实施方案包括：将含碳材料与溶剂中的有机重氮盐接触，可选择在有电解质存在的情况下进行，并使含碳材料相对于与所述重氮盐溶液分开的电解溶液接触的阳极负极化，其中电化学还原是在酸介质的质子溶剂中对有机重氮盐进行的。本发明教导了表面经有机基团修饰的含碳材料以及这些修饰材料的用途，例如用于生产复合材料或固定生物分子。
• Hewitt; Mann; Pope, Journal of the Chemical Society, 1914, vol. 105, p. 2195
  作者：Hewitt、Mann、Pope

  DOI：——

  日期：——