N-phenyl-N'-p-tolyl-triazene | 622-74-2

• 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: N-phenyl-N'-p-tolyl-triazene
• 英文别名: N-Phenyl-N'-p-tolyl-triazen；N-[(4-methylphenyl)diazenyl]aniline
• CAS: 622-74-2
• 化学式: C₁₃H₁₃N₃
• mdl: MFCD00459113
• 分子量: 211.266
• InChiKey: XBDIVOBVOAPQFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  36.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phenyl-N'-p-tolyl-triazene 在 sodiumsulfide nonahydrate 、 三氯乙酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.08h， 生成 苯硫酚
  参考文献：
  名称：

  在温和条件下从相关三氮烯中新型一锅法合成硫酚

  摘要：

  在这项工作中，首先从芳基伯胺合成三氮烯。然后，在酸性介质中使用硫化钠在一锅中将三氮烯转化为相应的苯硫酚，通过在室温下作为阴离子硫亲核试剂在硫化氢旁边原位生成重氮抗衡离子。该程序是从芳基伯胺制备苯硫酚的便捷捷径。

  DOI：

  10.1055/s-0032-1316557
• 作为产物：
  描述：

  苯胺 在 盐酸 、 水 、 sodium nitrite 作用下， 生成 N-phenyl-N'-p-tolyl-triazene
  参考文献：
  名称：

  Noelting; Binder, Chemische Berichte, 1887, vol. 20, p. 3016

  摘要：

  DOI：

文献信息

• Reactions of substituted 1,3-diphenyltriazenes with phenyl isocyanates. Catalysis and substituent effects
  作者：Blanka Plandorová、Oldřich Pytela、Miroslav Večeřa、Pavel Vetešník

  DOI：10.1135/cccc19801279

  日期：——

  Reactions of phenyl isocyanate with 12 monosubstituted and 15 symmetrical disubstituted 1,3-diphenyltriazanes have been studied in tetrahydrofurane at 25°C. The found rate constants correlate with the Hammett substituent constants, the slopes being - 1.206 and - 1.682 in case of the monosubstituted and the disubstituted compounds, respectively. Under conditions of pseudomonomolecular reaction catalysis by the products and that by the catalysts used in reactions of isocyanates with amines or hydroxy compounds have not been observed. Rates of reactions of 6 substituted phenyl isocyanates with the parent 1,3-diphenyltriazane have also been measured. In this case the found rate constants correlate with the Hammett substituent constants, the slope being +1.038. The results indicate that the reaction involves rate limiting formation of a six-membered cyclic complex which successively undergoes only a rapid reorganization of electrons.

  苯基异氰酸酯与12种单取代和15种对称双取代的1,3-二苯基三氮烷在25°C下在四氢呋喃中的反应已经研究。发现的速率常数与Hammett取代基常数相关，单取代化合物和双取代化合物的斜率分别为-1.206和-1.682。在伪单分子反应催化条件下，观察到了由产物和异氰酸酯与胺或羟基化合物反应中使用的催化剂引起的反应。还测量了6种取代苯基异氰酸酯与母体1,3-二苯基三氮烷的反应速率。在这种情况下，发现的速率常数与Hammett取代基常数相关，斜率为+1.038。结果表明，反应涉及限速形成一个六元环复合物，该复合物随后仅经历电子的快速重组。
• Metal-Free One-Pot Synthesis of<i>N</i>,<i>N′</i>-Diarylamidines and<i>N</i>-Arylbenzimidazoles from Arenediazonium Salts, Nitriles, and Free Anilines
  作者：So Won Youn、Eun Mi Lee

  DOI：10.1021/acs.orglett.6b02994

  日期：2016.11.4

  efficient and facile metal-free, one-pot reaction has been developed to afford diversely substituted N-arylbenzimidazoles through chemoselective in situ generation of N,N′-diarylamidines from arenediazonium salts, nitriles, and free anilines. The advantages of this protocol consist of the operationally easy and simple one-pot procedure under metal-free and mild conditions, the direct use of inexpensive

  已经开发了一种高效且简便的无金属单锅反应，可通过化学方法从槟榔二唑鎓盐，腈和游离苯胺中原位生成N，N'-二芳基idine胺，从而提供不同取代的N-芳基苯并咪唑。该协议的优点包括：在无金属和温和条件下操作简单，操作简单的一锅法；直接使用廉价和可商购的化学药品；因此，具有成本效益且更环保。
• 1,3-Diaryltriazenido complexes of bis-cyclopentadienylmolybdenum. Preparation and electrochemical behaviour
  作者：M.A.M. Queirós、J.E.J. Simão、A.R. Dias

  DOI：10.1016/s0022-328x(00)98897-1

  日期：1980.7

  [Mo(η-C5H5)2(p-R1C6H4NNN-p-C6H4R2)][PF6] (1) (R1 = R2 = H, F, CH3, OCH3; R1 = H, R2 = CH3, OCH3; R1 = CH3, R2 OCH3) have been prepared. The electrochemical behaviour of these complexes in acetonitrile has been studied by cyclic voltammetry and constant potential electrolysis at platinum electrodes. The complexes undergo two reversible one-electron reductions to species which are stable on the cyclic voltammetry

  新的配合物[沫（η-C 5 H ^ 5）2（p -R 1 C ^ 6 ħ 4 NNN- p -C 6 H ^ 4 - [R 2）] [PF 6 ]（1）（R 1 = R 2 = H ，F，CH 3，OCH 3 ; R 1 = H，R 2 = CH 3，OCH 3 ; R 1 = CH 3，R 2 OCH 3）已经准备好了。这些配合物在乙腈中的电化学行为已通过循环伏安法和铂电极上的恒电位电解进行了研究。络合物经历两次可逆的单电子还原，形成在循环伏安法时间尺度上稳定的物质，但是电子的吸收似乎伴随着三氮烯配体的损失。配合物的氧化电化学可以根据在第一次单电子氧化之后发生的歧化来合理化。还原电势和氧化电势均与σ + Hammett参数表现出良好的线性相关性，为配体R 1和R 2的介观影响提供了证据 氧化还原过程中涉及的金属轨道上的取代基。
• A Microwave Assisted Diazo Coupling Reaction: The Synthesis of Alkylazines and Thienopyridazines
  作者：Saleh Al-Mousawi、Abdel-Zaher Elassar、Morsy Ahmed El-Apasery

  DOI：10.1080/10426500500536457

  日期：2006.8.1

  Heating diazoaminobenzene with active methylene compounds 1-3 in microwave oven in acetic acid, in the presence of hydrochloric acid, afforded the corresponding arylhydrazones 5-7. These reaction products were condensed with ethyl cyanoacetate in a domestic microwave oven after 1-2 minutes heating to yield the pyridazinones 8-12. Compounds 8c and 12 reacted with sulfur in basic DMF solution, in microwave oven using MORE technology to yield the thienopyridazinone 14 and 16 respectively. While 17 was produced when 8b was treated like wise with sulfur and DMF in the presence of piperidine. Compounds 16 coupled with aromatic diazonium salts to yield arylazo derivatives 21a-c.
• Pd-Catalyzed C−H Activation/C−N Bond Formation: A New Route to 1-Aryl-1<i>H</i>-benzotriazoles
  作者：Rapolu Kiran Kumar、Md Ashif Ali、Tharmalingam Punniyamurthy

  DOI：10.1021/ol200523a

  日期：2011.4.15

  A method for the C-H activation of aryl triazene compounds followed by intramolecular amination is described. It involves the use of a catalytic amount of Pd(OAc)(2) that efficiently effects the cyclization to provide 1-aryl-1H-benzotriazoles at moderate temperature.