3-formyl-2-(phenylazo)-1H-indol | 1207105-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-formyl-2-(phenylazo)-1H-indol
• 英文别名: 2-phenyldiazenyl-1H-indole-3-carbaldehyde
• CAS: 1207105-96-1
• 化学式: C₁₅H₁₁N₃O
• 分子量: 249.272
• InChiKey: QGSDFXRAESSDSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  aniline hydrochloride 在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.09h， 生成 3-formyl-2-(phenylazo)-1H-indol
  参考文献：
  名称：

  固定在二氧化硅上的有机硅烷基亚硝酸盐离子液体的纳米颗粒，用于苯胺衍生物的重氮化和随后的偶氮染料的合成

  摘要：

  由N-甲基咪唑与（3-氯丙基）三甲氧基硅烷的反应制备含三甲氧基甲硅烷基的咪唑基亚硝酸盐离子液体。将该离子液体共价固定在二氧化硅上，得到亚硝酸咪唑鎓部分保持完整的纳米颗粒。进行重氮化反应作为模型反应，以检查这些纳米粒子作为硝鎓源的活性。在温和的非均相条件下（室温和较短的反应时间），在HCl存在下，各种苯胺衍生物的重氮化反应均表现出优异的性能。使用标准实验程序，将重氮盐与一系列叔苯胺，苯酚和萘酚进行原位偶联，以高收率提供了必要的偶氮染料。

  DOI：

  10.1016/j.dyepig.2011.09.013

文献信息

• Synthesis of a nitrite functionalized star-like poly ionic compound as a highly efficient nitrosonium source and catalyst for the diazotization of anilines and subsequent facile synthesis of azo dyes under solvent-free conditions
  作者：Hassan Valizadeh、Ashkan Shomali、Jalal Ghorbani、Saeideh Noorshargh

  DOI：10.1016/j.dyepig.2015.02.007

  日期：2015.6

  star-like poly ionic (NFSPI) compound was synthesized and used as a highly efficient nitrosonium source and catalyst for the conversion of aniline derivatives to diazonium salts. Azo dyes were prepared via in situ azo-coupling reaction of these diazoniums with active aromatic compounds under solvent-free conditions in very short reaction time in excellent yields. NFSPI plays dual role as a three-dimensional

  合成了亚硝酸盐官能化的星形聚离子（NFSPI）化合物，并将其用作高效的硝态氮源和催化剂，用于将苯胺衍生物转化为重氮盐。偶氮染料是通过在没有溶剂的条件下，这些重氮鎓与活性芳香族化合物在非常短的反应时间内以极高的收率进行原位偶氮偶合反应而制备的。NFSPI由于具有多离子特性，因此可作为三维硝态氮源和催化剂发挥双重作用。分离出的产物经FT-IR光谱，1 H-NMR，13确证。C-NMR光谱和CHNSO分析。通过FT-IR光谱，SEM图像，EDX和CHNSO分析确认了非均相试剂和催化剂的结构。通过该程序合成各种产物的产率和反应时间与文献报道的值进行了比较。
• New Generation of Nitrite Functionalized Star-like Polyvinyl Imidazolium Compound: Application as a Nitrosonium Source and Three Dimensional Nanocatalyst for the Synthesis of Azo Dyes
  作者：Ashkan Shomali、Hassan Valizadeh、Saeideh Noorshargh

  DOI：10.2174/1570178614666170321125216

  日期：2017.6.14

  Background: The compounds with three-dimensional and ionic structures have attracted considerable attentions because of their unique characteristics as a drug carrier and catalyst. Star-like poly ionic compounds are a new generation of three-dimensional structures which have both; the exclusive ionic features and three-dimensional structures. Recently, we reported the synthesis of diazonium salts from aniline derivatives using carboxyl and nitrite functionalized graphene quantum dots. Methods: Nitrite-functionalized star-like polyionic (NFSP) compound was synthesized as a new generation of three-dimensional nanocatalyst. Herein, the use of NFSP as an efficient reagent and nanocatalyst for the diazotization of aniline derivatives and subsequent synthesis of azo dyes via the reaction with active phenolates under solvent-free conditions was reported. Results: In order to demonstrate the positive impact of NFSP efficiency, the reaction times and yields of the products were compared with other methods and catalysts which have been reported previously. The brilliant performance of NFSP can be ascribed to multifunctional reagent and also trapping the ingredient within catalyst cavities. Conclusion: A highly effective and cost-effective method has been developed for the preparation of azo dyes. In reported method, new three-dimensional catalyst with highly ionic characteristic and multifunctional nitrosonium source is available. These special features reduced the required amount of catalyst, reaction time and also increased the efficiency of catalyst.

  背景：具有三维和离子结构的化合物因其作为药物载体和催化剂的独特特性而备受关注。星状多离子化合物是新一代的三维结构化合物，同时具有独特的离子特性和三维结构。最近，我们报道了利用羧基和亚硝基功能化石墨烯量子点从苯胺衍生物中合成重氮盐的方法：合成了亚硝酸盐功能化星状多离子（NFSP）化合物，作为新一代三维纳米催化剂。结果：为了证明 NFSP 效率的积极影响，将反应时间和产物产率与之前报道过的其他方法和催化剂进行了比较。 NFSP 的出色性能可归因于多功能试剂以及催化剂空腔内成分的捕获。 结论：已开发出一种高效、经济的偶氮染料制备方法。在报告的方法中，新型三维催化剂具有高离子特性和多功能硝基锍源。这些特点不仅减少了催化剂的用量，缩短了反应时间，还提高了催化剂的效率。
• Carboxyl and nitrite functionalized graphene quantum dots as a highly active reagent and catalyst for rapid diazotization reaction and synthesis of azo-dyes under solvent-free conditions
  作者：Hassan Valizadeh、Ashkan Shomali、Saideh Nourshargh、Rahim Mohammad-Rezaei

  DOI：10.1016/j.dyepig.2014.09.023

  日期：2015.2

  Carboxyl and nitrite functionalized graphene quantum dots was prepared from carboxyl and hydroxyl functionalized graphene quantum dots using NaNO2 in the absence of mineral acids. This functional group conversion was confirmed by FT-IR spectroscopy, photoluminescence and X-ray diffraction. The carboxyl and nitrite functionalized graphene quantum dots was used as an effective nitrosonium ion source and reusable catalyst for the efficient diazotization of a variety of arylamines without using any additional acid. Subsequent azo-coupling of these freshly prepared diazonium salts with a range of active aromatic compounds led to the requisite azo-dyes in excellent yields in very short reaction times with a simple experimental procedure. (C) 2014 Elsevier Ltd. All rights reserved.