N,N-dimethyl-4-(N'-phenyl-hydrazino)-aniline | 63042-07-9

• 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,N-dimethyl-4-(N'-phenyl-hydrazino)-aniline
• 英文别名: N-(4-Dimethylamino-phenyl)-N'-phenyl-hydrazin；N,N-Dimethyl-4-(N'-phenyl-hydrazino)-anilin；Benzenamine, N,N-dimethyl-4-(2-phenylhydrazino)-；N,N-dimethyl-4-(2-phenylhydrazinyl)aniline
• CAS: 63042-07-9
• 化学式: C₁₄H₁₇N₃
• 分子量: 227.309
• InChiKey: IPZQDLDEXCBOIT-UHFFFAOYSA-N

物化性质

• 沸点：
  301.7±34.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  27.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-4-(N'-phenyl-hydrazino)-aniline 在 三氯异氰尿酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.22h， 以90%的产率得到4-(dimethylamino)azobenzene
  参考文献：
  名称：

  三氯异氰尿酸介导的肼氧化脱氢：一种实用的化学氧化方法，以获取偶氮化合物

  摘要：

  使用环保的TCCA作为氧化剂，已实现了肼的高效，无金属化学氧化。该良性方案可直接获得THF中各种偶氮化合物，且产率极高。以此方式总共获得了35种偶氮化合物，并进行了放大制备。另外，还提出了一种合理的机制。分步经济的过程，温和的反应条件，操作简便，高反应效率和易于放大的规模凸显了该方法的实用性。

  DOI：

  10.1055/s-0039-1690052
• 作为产物：
  描述：

  4-(dimethylamino)azobenzene 在 ammonia borane 、 tris(quinolin-8-yl)phosphite 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 N,N-dimethyl-4-(N'-phenyl-hydrazino)-aniline
  参考文献：
  名称：

  使用简单的无环亚磷酸酯预催化剂转移氢化偶氮化合物与氨-硼烷

  摘要：

  三（喹啉-8-基）亚磷酸酯，P(Oquin)3，促进 H3N·BH3 (AB) 的脱氢和使用氨硼烷 (AB) 作为 H2 源的偶氮芳烃的转移氢化。偶氮芳烃的无金属还原在温和的反应条件下进行，在此条​​件下可以高产率地获得几种二苯肼衍生物。P(Oquin)3 对 AB 的反应性通过 NMR 原位测试进行评估。研究了反应速率、活化参数、氘动力学同位素效应（DKIE）和线性自由能关系。这种机械和动力学研究表明 P(Oquin)3 是一种前催化剂，并且 AB 可能参与反应途径的一个以上阶段。此外，动力学数据表明反应通过有序的过渡态进行，可能是缔合的。

  DOI：

  10.1002/ejic.201900572

文献信息

• Tuning the reduction power of supported gold nanoparticle photocatalysts for selective reductions by manipulating the wavelength of visible light irradiation
  作者：Xuebin Ke、Sarina Sarina、Jian Zhao、Xingguang Zhang、Jin Chang、Huaiyong Zhu

  DOI：10.1039/c2cc17977f

  日期：——

  Gold nanoparticles supported on CeO(2) were found to be efficient photocatalysts for three selective reductions of organic compounds at ambient temperatures, under irradiation of visible light; their reduction ability can be tuned by manipulating the irradiation wavelength.

  发现载于CeO（2）上的金纳米颗粒是有效的光催化剂，可在环境温度下在可见光照射下对有机化合物进行三次选择性还原。它们的还原能力可以通过控制照射波长来调节。
• AN EFFECT OF TRIFLUOROMETHYL GROUP ON PHOTOSENSITIZING BEHAVIOR OF BENZOPHENONE DERIVATIVES
  作者：Keisuke Takuma、Tokiya Kimura、Takaaki Sonoda、Hiroshi Kobayashi

  DOI：10.1246/cl.1984.881

  日期：1984.6.5

  2,2′-Bis(trifluoromethyl)benzophenone acted as an efficient and stable photosensitizer in energy transfer and hydrogen transfer reactions.

  在能量转移和氢转移反应中，2,2′-双（三氟甲基）二苯甲酮是一种高效稳定的光敏剂。
• Square Wave Voltammetry for Two-Step Surface Reductions
  作者：John J. O'De、Janet G. Osteryoung

  DOI：10.1021/ac960647v

  日期：1997.2.1

  Strongly adsorbed species on an electrode surface are used to create a stable, redox-modified surface. Square wave voltammetry is then used to degrade the surface electrochemically, as evidenced by the resulting voltammetric response. This process can be mathematically modeled as a quasi-reversible surface reaction coupled with a first-order irreversible surface reaction of the product. This is the simplest possible model that can explain a two-step surface reduction. Exemplary calculations for square wave voltammetry show a wide variety of peak shapes depending on rate constants and square wave amplitude. The reduction of Dimethyl Yellow (4-(dimethylamino)azobenzene) adsorbed on mercury is accurately described by this model. Characteristic parameters of the overall surface process are obtained from voltammograms by using the two-step model with nonlinear least-squares analysis (COOL). For Dimethyl Yellow in Britton−Robinson buffer (pH 6.00) at a surface concentration of 17.3 pmol cm-2, these parameters are as follows:  standard potential, E10 = −0.397 ± 0.001 V vs SCE; transfer coefficient for the first step, α1 = 0.43 ± 0.02; rate constant for the first step, k10 = 103 ± 8 s-1; transfer coefficient for the second step, α2 = 0.11 ± 0.04; and rate constant for the second step, k20 (referenced to E10) = 11.1 ± 1.7 s-1. Uncertainties are 95% confidence intervals derived from a pool of 11 voltammograms collected at different square wave amplitudes (Esw = 0−100 mV).

  电极表面的强吸附物种被用来创建一个稳定的氧化还原修饰表面。然后使用方波伏安法对表面进行电化学降解，由此产生的伏安反应可以证明这一点。这一过程在数学上可模拟为准可逆表面反应与产物的一阶不可逆表面反应。这是能够解释两步表面还原反应的最简单模型。方波伏安法的示例计算显示，根据速率常数和方波振幅的不同，峰形也多种多样。该模型准确地描述了吸附在汞上的二甲基黄（4-(二甲基氨基)偶氮苯）的还原过程。利用非线性最小二乘分析（COOL）的两步模型，可从伏安图上获得整个表面过程的特征参数。对于布氏-罗宾逊缓冲液（pH 6.00）中表面浓度为 17.3 pmol cm-2 的二甲基黄，这些参数如下：标准电位，E10 = -0.397 ± 0.001 V vs SCE；第一步的转移系数，α1 = 0.43 ± 0.02；第一步的速率常数 k10 = 103 ± 8 s-1；第二步的传递系数 α2 = 0.11 ± 0.04；第二步的速率常数 k20（参考 E10）= 11.1 ± 1.7 s-1。不确定度为 95% 的置信区间，由在不同方波振幅（Esw = 0-100 mV）下采集的 11 张伏安图得出。
• Structure requirements for anaerobe processing of azo compounds: Implications for prodrug design
  作者：Jason Gavin、Juan F. Marquez Ruiz、Kinga Kedziora、Henry Windle、Dermot P. Kelleher、John F. Gilmer

  DOI：10.1016/j.bmcl.2012.10.014

  日期：2012.12

  This Letter generalizes the metabolism of the azo class of compounds by Clostridium perfringens, an anaerobe found in the human colon. A recently reported 5-aminosalicylic acid-based prednisolone prodrug was shown to release the drug when incubated with the bacteria, while the para-aminobenzoic acid (PABA) based analogue did not. Instead, it showed a new HPLC peak with a relatively close retention time to the parent which was identified by LCMS as the partially reduced hydrazine product. This Letter investigates azoreduction across a panel of substrates with varying degrees of electronic and steric similarity to the PABA-based compound. Azo compounds with an electron donating group on the azo-containing aromatic ring showed immediate disproportionation to their parent amines without any detection of hydrazine intermediates by HPLC. Compounds containing only electron withdrawing groups are partially and reversibly reduced to produce a stable detectable hydrazine. They do not disproportionate to their parent amines, but regenerate the parent azo compound. This incomplete reduction is relevant to the design of azo-based prodrugs and the toxicology of azo-based dyes. (C) 2012 Elsevier Ltd. All rights reserved.
• Klamerth, Zeitschrift fur Naturforschung, 1953, vol. 8 b, p. 177,178 Anm. 9
  作者：Klamerth

  DOI：——

  日期：——