2-((2-aminophenyl)diazenyl)phenol | 1098074-42-0

• 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-((2-aminophenyl)diazenyl)phenol
• 英文别名: 2-[(2-Aminophenyl)diazenyl]phenol；2-[(2-aminophenyl)diazenyl]phenol
• CAS: 1098074-42-0
• 化学式: C₁₂H₁₁N₃O
• 分子量: 213.239
• InChiKey: STOGIMATOFGGOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 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：
  71
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  钌,三羰基二(三苯基膦)- 、 2-((2-aminophenyl)diazenyl)phenol 以 甲苯 为溶剂， 反应 6.0h， 以50%的产率得到
  参考文献：
  名称：

  Ruthenium and palladium complexes incorporating amino-azo-phenol ligands: Synthesis, characterization, structure and reactivity

  摘要：

  The ligands 2-((2-aminophenyl) diazenyl) phenol, HOL1-NH2, 1a; 2-((2-aminophenyl) diazenyl)-5-methylphenol, HOL2-NH2, 1b; and 2-((2-aminophenyl) diazenyl)-5-chlorophenol, HOL3-NH2, 1c, which are abbreviated as HOL-NH2, 1, afforded the complexes of compositions [(OL-NH) Pd(PPh3)], 2, and [(OL-NH)Ru(CO)(PPh3)(2)], 3, upon reaction with Na2PdCl4 and Ru(CO)(3)(PPh3)(3) respectively. In all the complexes the metals ions, Pd(II) or Ru(II), are coordinated by deprotonated ligand (OL-NH) 2 in tridentate (N, N, O) fashion. X-ray structures of [(OL2-NH)Pd(PPh3)], 2b, and [(OL1-NH)Ru(CO)(PPh3)(2)], 3a, were determined to confirm the molecular structures. The cyclic voltammograms of [(OL-NH) Ru(CO)(PPh3)(2)] exhibited two quasi reversible oxidative response near 0.25 and 1.12 V vs. SCE. The nature of HOMO as obtained by DFT calculations has been inspected to have an insight into the redox orbitals. The newly synthesized [(OL-NH) Pd(PPh3)], 2a, complexes exhibited catalytic activity toward the Suzuki, Heck, Cyanation and amination reactions. Catalytic activity of complex [(OL1-NH) Ru(CO)(PPh3)(2)], 3a, was examined for the conversion of ketones to corresponding alcohols by transfer hydrogen reactions. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.02.002
• 作为产物：
  描述：

  1-{[2-(phenylazo)phenyl]iminomethyl}-2-phenol 在 nickel(II) acetate tetrahydrate 、 双氧水 、 高氯酸 作用下， 生成 2-((2-aminophenyl)diazenyl)phenol
  参考文献：
  名称：

  钒（IV）氮杂多酚配合物的合成，结构和反应性：细胞毒性研究。

  摘要：

  游离配体2-{（邻羟基芳基）偶氮} -1-N-水杨基苯胺H（2）L [其中H（2）L = RC（6）H（4）N = NC（6）H （4）N = CH-C（6）H（4）OHR = H（2）L（1）的pH，H（2）L（2）的p-Me和H（2）L的p-Cl （3）]，是通过水杨醛与2-{（（邻羟基芳基）偶氮}}苯胺的缩合制备的。H（2）L与VOSO（4）的反应提供了氧钒络合物（L）V（O）（H（2）O）。（L（1））V（O）（H（2）O）络合物在循环伏安法中相对于SCE在0.7 V和-0.65 V下显示两个可逆响应。已经研究了（L（1））V（O）（H（2）O）对H（2）O（2）的催化活性，该反应引起有机硫醚氧化为亚砜和砜。（L（1））V（O）（H（2）O）的细胞毒性也已在人肺癌细胞上进行了检查。

  DOI：

  10.1039/b903352a

文献信息

• Synthesis of New Oxido-Vanadium Complexes: Catalytic Properties and Cytotoxicity
  作者：Uttam Das、Poulami Pattanayak、Manas Kumar Santra、Surajit Chattopadhyay

  DOI：10.3184/174751918x15168821806597

  日期：2018.1

  benzaldehyde with 2-(2-amino phenyl}diazenyl)phenol afforded the ligand 3-(2-(2-hydroxyphenyl)diazenyl)-4-alkylphenyliminomethyl)benzene-1,2-diol. Reaction of H2L with VOSO4. 5H2O gave the oxido-vanadium(IV) complexes [(L)VO], which exhibited a quasi-reversible oxidative cyclic voltammetric response in a V(IV)/V(V) oxidative process. The complexes act as catalysts in the oxidation of organic thioethers and

  2,3-二羟基苯甲醛与2-(2-氨基苯基}二烯基)苯酚反应得到配体3-(2-(2-羟基苯基)二烯基)-4-烷基苯基亚氨基甲基)苯-1,2-二醇。H2L 与 VOSO4 的反应。5H2O 得到氧化钒 (IV) 配合物 [(L)VO]，其在 V(IV)/V(V) 氧化过程中表现出准可逆的氧化循环伏安响应。该配合物在有机硫醚的氧化和苯酚的溴化中充当催化剂。对三种癌细胞系检查了它们的细胞毒性特性。
• Activation of ortho C–H bond by nickel(II) acetate or sodium tetrachloropalladate(II) in naphthyl imino derivatives of azobenzene
  作者：Debprasad Patra、Poulami Pattanayak、Jahar Lal Pratihar、Surajit Chattopadhyay

  DOI：10.1016/j.poly.2012.12.011

  日期：2013.3

  H represents the dissociable proton upon complexation and aryl groups of H2Lnap are phenyl for H2L1nap; p-methyl phenyl for H2L2nap and p-chloro phenyl for H2L3nap] with nickel acetate tetra hydrate or disodium tetrachloropalladate in methanol afforded M–C(aryl) bonded species of composition [M(Lnap)] (M = Ni(II) and Pd (II)). The dinegative (Lnap)2− ligands bind the Ni(II) or Pd(II) in tetradentate

  摘要1-[2-（芳基偶氮）苯基]亚氨基甲基} -2-萘酚与H2Lnap的反应[其中H表示络合时的可解离质子，H2Lnap的芳基为H2L1nap的苯基；用乙酸四水合镍或四氯钯酸二钠在甲醇中制得[H2L2nap的对甲基苯基和[H2L3nap]的对氯苯基]，得到组成为[M（Lnap）]的M–C（芳基）键合物质（M = Ni（II）和Pd （II））。负性（Lnap）2-配体以扭曲的正方形平面几何形状以四齿（C，N，N，O）方式结合Ni（II）或Pd（II）。配体和配合物通过光谱方法表征。确定H2L1nap，[Ni（L1nap）]和[Pd（L1nap）]的X射线结构以鉴定其特征。与间氯过苯甲酸（mCPBA）的反应，已经检查了TBHP和过氧化氢导致氧插入MC键中。已经报道了配体和配合物的发光性质。
• Tetranuclear assembly of palladium(II): Catalyst for C–C coupling reactions
  作者：Poulami Pattanayak、Jahar Lal Pratihar、Debprasad Patra、Chia-Her Lin、Surajit Chattopadhyay

  DOI：10.1016/j.poly.2013.07.020

  日期：2013.10

  The 2-((2-benzylamino)phenyldiazenyl)phenol, H2OL [where H2OL = ArOHN = NC6H4N(H)CH2(C6H5); Ar = C6H5 (for H2OL1). P-MeC6H4 (for H2OL2) or p-ClC6H4 (for H2OL3)], ligands were prepared by the reaction of the appropriate 2-((2-hydroxyaryl)azo)anilines with benzyl bromide. The reactions of Na2PdCl4 with H2OL afforded tetranuclear Pd(II) complexes of the composition [pd(OL)](4). The ligands bind palladium(II) in a tridentate (N, N, O) fashion. The X-ray structure of [Pd(OL1)](4) was determined to confirm the characterization. The newly synthesized [Pd(OL1)](4) complex was utilized as a catalyst for the Suzuki and Heck reaction for a variety of substrates. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of uranium complexes incorporating extended azo-imine ligands: Molecular and electronic structure
  作者：Poulami Pattanayak、Sankar Prasad Parua、Debprasad Patra、Paula Brandão、Vitor Felix、Ashoke Prasun Chattopadhyay、Surajit Chattopadhyay

  DOI：10.1016/j.jics.2021.100049

  日期：2021.4