N,N'-dimethyl-N,N'-bis-(p-cyanophenyl)hydrazine | 79121-26-9

• 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-N,N'-bis-(p-cyanophenyl)hydrazine
• 英文别名: N,N'-dimethyl-N,N'-bis(p-cyanophenyl)hydrazine；1,2-Bis(p-cyanophenyl)-1,2-dimethylhydrazine；4,4'-(dimethyl-hydrazo)-di-benzonitrile；4,4'-(Dimethyl-hydrazo)-di-benzonitril；4-[(4-cyano-N-methylanilino)-methylamino]benzonitrile
• CAS: 79121-26-9
• 化学式: C₁₆H₁₄N₄
• 分子量: 262.314
• InChiKey: ZIIYAFJBIGAAPS-UHFFFAOYSA-N

物化性质

• 熔点：
  197-198 °C(Solv: ethanol (64-17-5))
• 沸点：
  454.1±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.06
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4-[[(E)-(4-cyano-N-methylanilino)diazenyl]-methylamino]benzonitrile 以21%的产率得到
  参考文献：
  名称：

  BAE, DONG, HAK;SHINE, H. J., J. ORG. CHEM., 1981, 46, N 23, 4700-4704

  摘要：

  DOI：

文献信息

• The kinetics and mechanisms of oxygen transfer in the reaction of p-cyano-N,N-dimethylaniline N-oxide with metalloporphyrin salts. 4. Catalysis by meso-[tetrakis(2,6-dimethylphenyl)porphinato]iron(III) chloride
  作者：T. C. Woon、C. Michael. Dicken、Thomas C. Bruice

  DOI：10.1021/ja00285a018

  日期：1986.12

  8/TPP)Fe/sup III/OCH/sub 3/ are comparable to those of the unsubstituted meso-(tetraphenyl-porphinato)iron(III) methoxide ((TPP)Fe/sup III/OCH/sub 3/). The following results are, therefore, not surprising: (i) the second-order rate constant (k/sub a/k/sub b//k/sub -a/) for reaction of Me/sub 8/TPP)Fe/sup III/Cl with NO is but 3.3-fold smaller than in the case of the reaction of NO with (TPP)Fe/sup III/Cl; (ii)

  meso-(Tetrakis(2,6-二甲基苯基)porphinato)铁(III)氯化物 (Me/sub 8/ TPP)Fe/sup III/Cl) 是转化对氰基-N,N-二甲基苯胺 N 的催化剂-氧化物 (NO) 到对氰基-N,N-二甲基苯胺 (DA)、对氰基-N-甲基苯胺 (MA)、对氰基-N-甲酰基-N-甲基苯胺 (FA)、对氰基苯胺 (A) )、N,N'-二甲基-N,N'-双(对氰基苯基)肼(H)、N,N'-双(对氰基苯基)-N-甲基亚甲基二胺(MD)和CH/sub 2/哦。所有证据都支持这些反应是通过 NO 与铁 (III) 卟啉的平衡连接而发生的，然后是决定速率的氧转移以产生直接产物 DA 和铁 (IV)-氧代卟啉..pi..-阳离子自由基。DA 被更高价的铁-氧卟啉物质逐步氧化是形成其他产物的原因（即 DA ..-->.. ..-->.. FA, DA ..-->.. MA
• Kinetics and mechanism of oxygen transfer in the reaction of p-cyano-N,N-dimethylaniline N-oxide with metalloporphyrin salts. 6. Oxygen atom transfer to and from the iron(III) C2cap porphyrin of Baldwin
  作者：Thomas C. Bruice、C. Michael Dicken、P. N. Balasubramanian、T. C. Woon、Fu Lung Lu

  DOI：10.1021/ja00245a040

  日期：1987.5

  the SbF/sub 6//sup -/ salt of the C/sub 2/-capped (meso-tetraphenylporphinato)iron(III) of Baldwin ((TPPC/sub 2/cap)Fe/sup III/SbF/sub 6/). Since neither NO nor the SbF/sub 6//sup -/ anion can fit under the cap, this result establishes that oxygen transfer from NO to the iron(III) center can occur without the intermediate iron(IV)-oxo porphyrin ..pi..-cation being hexacoordinated. The products of NO decomposition

  对氰基-N,N-二甲基苯胺 N-氧化物 (NO) 的分解由 SbF/sub 6//sup 催化 (CH/sub 2/Cl/sub 2/ 溶剂 at 25 /sup 0/C) /鲍德温的 C/sub 2/-封端（内消旋四苯基卟啉）铁（III）的盐（（TPPC/sub 2/cap）Fe/sup III/SbF/sub 6/）。由于 NO 和 SbF/sub 6//sup -/ 阴离子都不能容纳在帽盖下，因此该结果表明，在没有中间体铁 (IV)-氧代卟啉的情况下，可以发生从 NO 到铁 (III) 中心的氧转移。 pi..-阳离子被六配位。NO分解产物（对氰基-N,N-二甲基苯胺（DA）68%，对氰基-N-甲基苯胺（MA）12%，对氰基苯胺（A）1%，N-甲酰基-对氰基） -N-甲基苯胺（FA）6%，N,N'-二甲基-N,N'-双（对氰基苯基）肼（H）7%，CH/sub 2/O 3%）占100%
• Kinetics and mechanism of oxygen transfer in the reaction of p-cyano-N,N-dimethylaniline N-oxide with metalloporphyrin salts. 7. Oxygen atom transfer to and from [meso-tetrakis(pentafluorophenylporphinato]iron(III) chloride
  作者：Drazen Ostovic、Carolyn B. Knobler、Thomas C. Bruice

  DOI：10.1021/ja00245a041

  日期：1987.5

  The authors report herein an investigation of the reaction of NO with (meso-tetrakis(pentafluorophenyl)porphinato)iron(III) chloride ((F/sub 20/TPP)Fe/sup III/Cl). The salt (F/sub 20/TPP)Fe/sup III/Cl represents the most electron-deficient iron(III) porphyrin which has been examined. The authors findings include the observations that a large portion of DA oxidation occurs prior to the diffusion apart

  作者在此报告了对 NO 与（内消旋四（五氟苯基）卟吩合）氯化铁（III）（（F/sub 20/TPP）Fe/sup III/Cl）反应的研究。盐 (F/sub 20/TPP)Fe/sup III/Cl 代表已检测到的最缺电子的铁 (III) 卟啉。作者的发现包括观察到大部分 DA 氧化发生在 DA 和 ((/sup +/F/sub 20/TPP)Fe/sup IV/O)Cl 扩散之前。此外，他们发现在溶剂笼/((/sup +/F/sub 20/TPP)Fe/sup IV/O)Cl x DA/DA 的芳环羟基化的两个反应（以前没有的特征）在 NO 与其他取代的四苯基卟啉的反应中观察到）和 DA 的去甲基化同等竞争。
• Kinetics and mechanisms of oxygen transfer in the reaction of p-cyano-N,N-dimethylaniline N-oxide with metalloporphyrin salts. 2. Amine oxidation and oxygen transfer to hydrocarbon substrates accompanying the reaction of p-cyano-N,N-dimethylaniline N-oxide with meso-(tetraphenylporphinato)iron(III) chloride
  作者：C. Michael Dicken、Fu Lung Lu、Michael W. Nee、Thomas C. Bruice

  DOI：10.1021/ja00306a027

  日期：1985.10
• Kinetics and mechanism of oxygen transfer in the reaction of p-cyano-N,N-dimethylaniline N-oxide with metalloporphyrin salts. 5. The influence of imidazole ligation of (meso-tetrakis(2,6-dimethylphenyl)porphinato)manganese(III) chloride on the rates of oxygen transfer from N-oxide to metalloporphyrin salt and the efficiency of oxidations by the intermediate higher valent manganese-oxo species
  作者：Wah Hun Wong、Drazen Ostovic、Thomas C. Bruice

  DOI：10.1021/ja00245a039

  日期：1987.5