5-苯基-1H-四唑乙酸乙酯 | 42606-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 5-苯基-1H-四唑乙酸乙酯
• 英文名称: 7-nitroquinoline-8-amine
• 英文别名: 8-amino-7-nitroquinoline；7-nitroquinolin-8-amine；7-nitro-8-aminoquinoline；7-nitro-quinolin-8-ylamine；7-nitro-[8]quinolylamine；7-Nitro-[8]chinolylamin
• CAS: 42606-35-9
• 化学式: C₉H₇N₃O₂
• 分子量: 189.173
• InChiKey: GKEHJLSFVXBUPA-UHFFFAOYSA-N

物化性质

• 熔点：
  185-185.5 °C
• 沸点：
  409.4±30.0 °C(Predicted)
• 密度：
  1.445±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-苯基-1H-四唑乙酸乙酯 在 肼 作用下， 以 乙醇 为溶剂， 生成 2,3-dimethyl-pyrido[2,3-f]quinoxaline
  参考文献：
  名称：

  Controlling Ground and Excited State Properties through Ligand Changes in Ruthenium Polypyridyl Complexes

  摘要：

  The capture and storage of solar energy requires chromophores that absorb light throughout the solar spectrum. We report here the synthesis, characterization, electrochemical, and photophysical properties of a series of Ru(II) polypyridyl complexes of the type [Ru(bpy)(2)(N-N)](2+) (bpy = 2,2'-bipyridine; N-N is a bidentate polypyridyl ligand). In this series, the nature of the N-N ligand was altered, either through increased conjugation or incorporation of noncoordinating heteroatoms, as a way to use ligand electronic properties to tune redox potentials, absorption spectra, emission spectra, and excited state energies and lifetimes. Electrochemical measurements show that lowering the pi* orbitals on the N-N ligand results in more positive Ru3+/2+ redox potentials and more positive first ligand-based reduction potentials. The metal-to-ligand charge transfer absorptions of all of the new complexes are mostly red-shifted compared to Ru(bpy)(3)(2+) (lambda(max) = 449 nm) with the lowest energy MLCT absorption appearing at lambda(max) = 564 nm. Emission energies decrease from lambda(max) = 650 nm to 885 nm across the series. One-mode Franck-Condon analysis of room-temperature emission spectra are used to calculate key excited state properties, including excited state redox potentials. The impacts of ligand changes on visible light absorption, excited state reduction potentials, and Ru3+/2+ potentials are assessed in the context of preparing low energy light absorbers for application in dye-sensitized photoelectrosynthesis cells.

  DOI：

  10.1021/ic500408j
• 作为产物：
  描述：

  间硝基苯胺 在 氢氧化钾 、 arsenic(V) oxide 、 硫酸 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 5-苯基-1H-四唑乙酸乙酯
  参考文献：
  名称：

  Condensed Heterocycles; Xl. Synthesis of 1,2,5-Thia(selena)diazolo[3,4-b]quinolines and 1,2,5-Thia(selena)diazolo[3,4-h]quinolines

  摘要：

  DOI：

  10.1055/s-1981-29435

文献信息

• A First Example of Cobalt-Catalyzed Remote CH Functionalization of 8-Aminoquinolines Operating through a Single Electron Transfer Mechanism
  作者：Christopher J. Whiteoak、Oriol Planas、Anna Company、Xavi Ribas

  DOI：10.1002/adsc.201600161

  日期：2016.5.19

  through a single electron transfer (SET) mechanism, although requiring elevated reaction temperatures. Herein, we described the first example of a cobalt‐catalyzed remote CH functionalization of 8‐aminoquinoline compounds operating through a SET mechanism, exemplified using a practical and mild nitration protocol. The reaction uses inexpensive cobalt nitrate hexahydrate [Co(NO3)2⋅6 H2O] as catalyst and

  的新的C开发基于廉价的钴催化剂^ h功能化协议，正在引起显著的兴趣。功能化的8-氨基喹啉化合物是有机化学和药物化合物中的高潜力基石，制备它们的新捷径将非常有价值。近年来，铜已被用作8-氨基喹啉化合物功能化的催化剂，尽管需要提高反应温度，但铜仍可通过单电子转移（SET）机理起作用。在这里，我们描述了钴催化的远程C的第一个例子通过SET机制运作的8-氨基喹啉化合物的H功能化，以实用而温和的硝化方案为例。该反应使用硝酸钴六水合物便宜[CO（NO 3）2 ⋅6ħ 2 O]为催化剂和叔亚硝酸叔丁酯（TBN）为硝基源。该方法学为轻松制备许多新的功能化8-氨基喹啉衍生物提供了基础。
• Regioselective C-7 Nitration of 8-Aminoquinoline Amides Using <i>tert</i> -Butyl Nitrite
  作者：Susmita Mondal、Sadhanendu Samanta、Alakananda Hajra

  DOI：10.1002/adsc.201701555

  日期：2018.3.1

  using tert‐butyl nitrite under metal‐free conditions at ambient temperature. The protocol is applicable to various aryl, heteroaryl as well as aliphatic carboxamides, and exhibits high functional group compatibility. The present method provides selective mononitrated quinoline derivatives. Experimental results suggest that the reaction likely proceeds through a radical pathway.

  在环境温度下，在无金属条件下，使用亚硝酸叔丁酯可实现8-氨基喹啉酰胺的区域选择性C-7硝化。该协议适用于各种芳基，杂芳基以及脂肪族羧酰胺，并具有较高的官能团相容性。本方法提供了选择性的单硝化喹啉衍生物。实验结果表明该反应可能通过自由基途径进行。
• Vicarious nucleophilic amination of nitroquinolines by 1,1,1-trimethylhydrazinium iodide
  作者：Maria Grzegożek

  DOI：10.1002/jhet.5570450652

  日期：2008.11

  The amination of 3-, 5-, 6-, 7- and 8-nitroquinoline via the vicarious nucleophilic substitution of hydrogen (VNS) with 1,1,1-trimethylhydrazinium iodide (TMHI) in the presence of t-BuOK in DMSO was studied. The amination occurs regioselectively giving ortho or ortho and para isomers relative to the nitro group with a high yield (95-86%). 2-Nitroquinoline does not undergo vicarious amination but displacement

  在存在t -BuOK的DMSO中，通过1,1,1-三甲基碘化氢碘（TMHI）通过氢（VNS）的取代核亲核取代（VNS）进行了3-，5-，6-，7-和8-硝基喹啉的胺化反应。研究过。胺化以区域选择性地产生相对于硝基的邻，邻，邻和对和对异构体，产率高（95-86％）。2-硝基喹啉不进行取代胺化，但是不稳定的硝基被氨基取代，然后转化为亚胺化合物并水解得到2（1H）-喹啉酮。
• Vicarious nucleophilic amination of nitroquinolines with 4-amino-1,2,4-triazole
  作者：Barbara Szpakiewicz、Maria Grzegożek

  DOI：10.1139/v08-051

  日期：2008.7.1

  3-, 5-, 6-, 7- and 8-Nitroquinolines react with 4-amino-1,2,4-triazole in basic medium (potassium tert-butoxide-dimethyl sulfoxide) giving amino products of the vicarious nucleophilic substitution (VNS) of hydrogen, predominantly at ortho position to the nitro group, except 8-nitroquinoline, which reacts at para position. Additionally, furazano[3,4-f]- and furazano[3,4-h]quinoline were obtained in the case of 5- and 8- nitroquinoline, respectively. 2-Nitroquinoline was aminated to 2-quinolino(1,2,4-triazol-4-yl)amine in these conditions.Key words: nitroquinolines, vicarious nucleophilic substitution (VNS), 4-amino-1,2,4-triazole.

  3-、5-、6-、7-和 8-硝基喹啉与 4-氨基-1,2,4-三唑在碱性介质（叔丁醇钾-二甲亚砜）中发生反应，产生氢的代亲核取代（VNS）氨基产物，主要位于硝基的正位，但 8-硝基喹啉除外，它在对位发生反应。此外，5-硝基喹啉和 8-硝基喹啉分别得到了呋喃并[3,4-f]-喹啉和呋喃并[3,4-h]喹啉。在这些条件下，2-硝基喹啉被胺化为 2-氨基喹啉（1,2,4-三唑-4-基）胺。
• Developing Metal-Binding Isosteres of 8-Hydroxyquinoline as Metalloenzyme Inhibitor Scaffolds
  作者：Hyeonglim Seo、Moritz K. Jackl、Mark Kalaj、Seth M. Cohen

  DOI：10.1021/acs.inorgchem.2c00891

  日期：2022.5.16

  utilized by medicinal chemists to navigate these issues during the drug development process. The quinoline pharmacophore and its bioisosteres, such as quinazoline, are important building blocks in the design of new therapeutics. More relevant to metalloenzyme inhibition, 8-hydroxyquinoline (8-HQ) and its derivatives can serve as MBPs for metalloenzyme inhibition. In this report, 8-HQ isosteres are designed

  在基于片段的药物发现中使用金属结合药效团 (MBP) 已被证明对靶向金属酶药物开发有效。然而，MBPs 仍然会受到药代动力学的影响。生物等排物替代是药物化学家在药物开发过程中解决这些问题的有效策略。喹啉药效团及其生物电子等排体，如喹唑啉，是新疗法设计的重要组成部分。与金属酶抑制作用更相关的是，8-羟基喹啉 (8-HQ) 及其衍生物可作为金属酶抑制作用的 MBP。在本报告中，设计了 8-HQ 等排体，并使用生物无机模型复合物探索了所得金属结合等排体 (MBI) 的配位化学。此外，研究了这些 MBI 的物理化学性质和金属酶抑制活性，以建立药物样特征。本报告提供了一组新的 8-HQ 衍生的 MBI，它们可以作为金属酶抑制剂开发的新型支架，具有可调和可能改善的物理化学特性。