1-(phenyldiazenyl)naphthalen-2,6-diol | 115440-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(phenyldiazenyl)naphthalen-2,6-diol
• 英文别名: 1-phenylazo-2,6-dihydroxtnaphthalene；1-Phenylazo-2,6-dihydroxynaphthalene；1-phenyldiazenylnaphthalene-2,6-diol
• CAS: 115440-09-0
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: JVWRDWIVNBPMRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,6-萘二酚 、 苯胺 在 盐酸 、 sodium nitrite 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 以31%的产率得到1-(phenyldiazenyl)naphthalen-2,6-diol
  参考文献：
  名称：

  1-（苯基二氮烯基）萘-2-醇中受激质子转移的概念

  摘要：

  一系列萘酚（的芳基偶氮衍生物的1 - 3）通过的UV-Vis和在不同溶剂中，以及通过量子化学计算和X射线分析NMR光谱方法研究。先前的研究表明，苏丹I（1）以互变异构混合物的形式存在。通过现有的分子内氢键使溶剂的影响最小化。因此，已经研究了对结构修饰的1中互变异构状态的影响。结构2包含另外的OH-基团，其易于去质子化并通过改变取代基的电子性质影响互变异构平衡的位置。在3中实施侧臂为来自偶氮基团的氮和来自哌啶单元的氮之间的互变异构质的竞争创造了条件。在这种情况下，实现了使用酸作为刺激来控制互变异构过程。

  DOI：

  10.1016/j.dyepig.2018.03.070

文献信息

• Oxidation of xenobiotics by plant microsomes, a reconstituted cytochrome P450 system and peroxidase: a comparative study
  作者：M Stiborová、H.H Schmeiser、E Frei

  DOI：10.1016/s0031-9422(00)00123-0

  日期：2000.6

  The microsomal fraction from tulip bulbs (Tulipa fosteriana, L.) contains cytochrome P450 (CYP3, EC 1.14.14.1) and peroxidase (EC 1.11.1.7.) enzymes catalyzing the NADPH - and hydrogen peroxide - dependent oxidation of the xenobiotic substrates, N-nitrosodimethylamine (NDMA), Nw-nitrosomethylaniline (NMA), aminopyrine and 1-phenylazo 2-hydroxynaphthalene (Sudan I), respectively. Oxidation of these model xenobiotics has also been assessed in a reconstituted electron-transport chain with a partially purified CYP fraction, phospholipid and isolated tulip NADPH:CYP reductase (EC 1.6.2.4.). Peroxidase isolated from tulip bulbs (isoenzyme C) oxidizes these xenobiotics, too. Values of kinetic parameters (K-m, V-max), requirements for cofactors (NADPH, hydrogen peroxide), the effect of inhibitors and identification of products formed from the xenobiotics by the microsomal fraction, partially purified CYP and peroxidase C were determined. These data were used to estimate the participation of the CYP preparation and peroxidase C in oxidation of two out of the four studied xenobiotics (NMA, Sudan I) in tulip microsomes. Using such detailed study, we found that the CYP-dependent enzyme system is responsible for the oxidation of these xenobiotics in the microsomal fraction of tulip bulbs. The results demonstrate the progress in resolving the role of plant CYP and peroxidase enzymes in oxidation of xenobiotics. (C) 2000 Elsevier Science Ltd. All rights reserved.
• A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols
  作者：S. Hristova、V. Deneva、M. Pittelkow、A. Crochet、F.S. Kamounah、K.M. Fromm、P.E. Hansen、L. Antonov

  DOI：10.1016/j.dyepig.2018.03.070

  日期：2018.9

  shown that Sudan I (1) exists as a tautomeric mixture. The effect of the solvents is minimized by the existing intramolecular hydrogen bond. Therefore, the influence on the tautomeric state in structurally modified 1 has been investigated. Structure 2 contains an additional OH-group, which deprotonates easily and affects the position of the tautomeric equilibrium by changing the electronic properties

  一系列萘酚（的芳基偶氮衍生物的1 - 3）通过的UV-Vis和在不同溶剂中，以及通过量子化学计算和X射线分析NMR光谱方法研究。先前的研究表明，苏丹I（1）以互变异构混合物的形式存在。通过现有的分子内氢键使溶剂的影响最小化。因此，已经研究了对结构修饰的1中互变异构状态的影响。结构2包含另外的OH-基团，其易于去质子化并通过改变取代基的电子性质影响互变异构平衡的位置。在3中实施侧臂为来自偶氮基团的氮和来自哌啶单元的氮之间的互变异构质的竞争创造了条件。在这种情况下，实现了使用酸作为刺激来控制互变异构过程。