N,N-dimethyl-1-naphthyl-4[(E)-2-phenyldiazen-1-yl]aniline

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-dimethyl-1-naphthyl-4[(E)-2-phenyldiazen-1-yl]aniline
• 英文别名: trans-naphthalene-1-azo-(4'-dimethylaminobenzene)；Naphthalene-1-azo-(4'-(dimethylamino)benzene)
• 化学式: C₁₈H₁₇N₃
• 分子量: 275.353
• InChiKey: RKGIHRYVFSZPKN-FMQUCBEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  27.96
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  Naphthalene-1-azo-(4'-(dimethylamino)benzene) 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 N,N-dimethyl-1-naphthyl-4[(E)-2-phenyldiazen-1-yl]aniline
  参考文献：
  名称：

  Effect of Hydroxide Ion on the Cis-Trans Thermal Isomerization of Azobenzene Derivatives

  摘要：

  Azobenzenes can be photochemically transformed from the trans (E) form, which is thermodynamically more stable, to the cis (Z) form. In the dark, the latter reverts to the former. We report here a kinetic study of the thermal isomerization ion of methyl orange (1), 4-(dimethylamino)-4'-methoxyazobenzene (2), and naphthalene-1-azo-(4'-(dimethylamino)benzene) (3) in water or in water/cosolvent solution measured at different hydroxide ion concentrations. It was found that the reaction is strongly dependent on the hydroxide ion concentration. The observed rate constant for 2 changes from 1.43 x 10(-2) s(-1) at NaOH(1.0 x 10(-3) M) to 7.7 x 10(-4) s(-1) at NaOH (0.10 M). These results can be interpreted in terms of the isomerization rate constant of the protonated substrates which is at least 10(8) times faster than that of the neutral compound.

  DOI：

  10.1021/jo00115a010

文献信息

• 一种高立体选择性制备反式芳香叔胺偶氮类 化合物的方法
  申请人：湖南理工学院

  公开号：CN107935882B

  公开（公告）日：2020-11-13

  本发明提供了一种高效、高选择性对有机芳香叔胺芳环对位C‑H键选择性活化制备偶氮化合物的方法，其采用布朗斯特酸作为催化剂，以芳基重氮四氟硼酸盐类化合物与有机芳香叔胺类化合物作为反应底物，反应体系加入了有机溶剂。该方法的优点：催化剂廉价易得；底物适用性高；反应条件温和，安全可靠；所得目标产物的选择性接近100%，E/Z选择性大于99:1，产率较高。该方法解决了传统合成不同芳基官能团取代有机芳香叔胺偶氮类化合物的反应条件苛刻、反应选择性差、实验步骤繁琐、产率低以及需要用到对环境有害试剂等不足，具有良好的工业应用前景。本发明同时还提供了对应的含不同芳基取代官能团的有机芳香叔胺偶联类化合物。
• Effect of Hydroxide Ion on the Cis-Trans Thermal Isomerization of Azobenzene Derivatives
  作者：Ana M. Sanchez、Rita H. Rossi

  DOI：10.1021/jo00115a010

  日期：1995.5

  Azobenzenes can be photochemically transformed from the trans (E) form, which is thermodynamically more stable, to the cis (Z) form. In the dark, the latter reverts to the former. We report here a kinetic study of the thermal isomerization ion of methyl orange (1), 4-(dimethylamino)-4'-methoxyazobenzene (2), and naphthalene-1-azo-(4'-(dimethylamino)benzene) (3) in water or in water/cosolvent solution measured at different hydroxide ion concentrations. It was found that the reaction is strongly dependent on the hydroxide ion concentration. The observed rate constant for 2 changes from 1.43 x 10(-2) s(-1) at NaOH(1.0 x 10(-3) M) to 7.7 x 10(-4) s(-1) at NaOH (0.10 M). These results can be interpreted in terms of the isomerization rate constant of the protonated substrates which is at least 10(8) times faster than that of the neutral compound.
• Effect of β-Cyclodextrin on the Thermal Cis−Trans Isomerization of Azobenzenes
  作者：Ana M. Sanchez、Rita H. de Rossi

  DOI：10.1021/jo951028+

  日期：1996.1.1

  The cis-trans thermal isomerization of p-methyl red (1), o-methyl red (2), and methyl orange (3) was inhibited by beta-cyclodextrin (beta-CD) at constant pH. Their isomerization rate decreased 4, 8, and 1.67 times, respectively, in a solution containing 0.01 M beta-CD. This effect can be attributed to the formation of an inclusion complex between the substrate and beta-CD which hinders the rotation of the N=N bond. The isomerization rate of methyl yellow (4), 4-(dimethylamino)-4'-methoxy-azobenzene (5), and naphthalene-1-azo[4'-(dimethylamino)benzene] (6) was not affected by beta-CD due to the presence of an organic cosolvent in the solution which displaces the azobenzene from the cavity, and the complex formed is probably equatorial. In addition, the transition state for the isomerization of compounds 1-3 involves rotation and that of 4-6, which have only electron-donating groups, inversion. This latter process brings about less volume change than rotation so it is less hindered by the complexation with beta-CD.