5-bromo-1-butylindoline-2,3-dione | 332929-55-2

• 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: 5-bromo-1-butylindoline-2,3-dione
• 英文别名: 5-Bromo-1-butyl-1H-indole-2,3-dione；5-bromo-1-butylindole-2,3-dione
• CAS: 332929-55-2
• 化学式: C₁₂H₁₂BrNO₂
• mdl: MFCD02108042
• 分子量: 282.137
• InChiKey: OQHCOYLIOZLIKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  5-bromo-1-butylindoline-2,3-dione 在 bis-triphenylphosphine-palladium(II) chloride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 4-(5-(6-butyl-6H-indolo[2,3-b]quinoxalin-9-yl)thiophen-2-yl)-N,N-diphenylaniline
  参考文献：
  名称：

  Synthesis, Spectra, and Theoretical Investigations of the Triarylamines Based on 6H-Indolo[2,3-b]quinoxaline

  摘要：

  Triarylamines containing a 6H-indolo[2,3-b]quinoxaline core and aromatic units such as phenyl, naphthyl, pyrene, anthracene, or fluorene have been synthesized by employing palladium-catalyzed C-N and C-C coupling reactions and characterized by optical absorption and emission spectra, electrochemical behavior, and thermal studies. Even though the electronic absorption spectra of the compounds were influenced by the nature of the peripheral amines, the emission spectra indicated close similarity for the excited states in these compounds. For the derivatives in which the amines were directly anchored on the 6H-indolo[2,3-b]quinoxaline nucleus, the emission appeared to be dominated by the state localized on the 6H-indolo[2,3-b]quinoxaline chromophore, while in the compounds containing the extended conjugation the fluorescence originated from the polyaromatic linker. The compounds displayed green or yellow emission depending on the nature of the amine segment. All of the dyes displayed one-electron quasi-reversible oxidation couple in the cyclic voltammograms, which is attributable to the oxidation of the peripheral amines at the 6H-indolo[2,3-b]-quinoxaline core. An additional one-electron oxidation process observable at the high positive potentials for the compounds 7 and 8 probably arises from the oxidation of the arylthiophene segment. The enhanced thermal stability and relatively higher glass transition temperatures observed for these compounds were attributed to the presence of dipolar 6H-indolo[2,3-b]quinox. aline segment. The origin of the optical spectra and the trends observed therein were rationalized using TDDFT simulations.

  DOI：

  10.1021/jo1016663
• 作为产物：
  描述：

  N-(4-bromophenyl)-2-(hydroxyimino) acetamide 在 硫酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-bromo-1-butylindoline-2,3-dione
  参考文献：
  名称：

  Design and Synthesis of 3-Substituted Indolin-2-one Derivatives with Methyl (E)-2-(3-Methoxy)acrylate Moiety

  摘要：

  本文设计并合成了15种含甲基（E）-2-（3-甲氧基）丙烯酸酯基团的吲哚-2-酮衍生物，并通过1H NMR、IR和HR-MS谱图分析确证了目标化合物的结构。

  DOI：

  10.14233/ajchem.2015.18286

文献信息

• Mild and efficient synthesis of isoindigo derivatives catalyzed by Lewis acid
  作者：Meilin Liu、Shaozhong Qiu、Yu Ye、Guodong Yin

  DOI：10.1016/j.tetlet.2016.11.053

  日期：2016.12

  A mild and efficient ZrCl4-catalyzed synthesis of isoindigo derivatives from isatins and indolin-2-ones in refluxing ethanol is described. A variety of new functionalized isoindigo derivatives are obtained by simple filtration. Lewis acid was first used as catalyst in the synthesis of isoindigo derivatives.

  描述了在回流的乙醇中温和且有效的ZrCl 4催化从靛红和吲哚-2-酮合成异靛蓝衍生物的方法。通过简单的过滤就可以得到许多新的功能化的异靛蓝衍生物。路易斯酸首先在异靛蓝衍生物的合成中用作催化剂。
• Copper-catalyzed aerobic oxidative intramolecular amidation of 2-aminophenylacetylenes: a domino process for the synthesis of isatin
  作者：N. Salvanna、Perla Ramesh、K. Santosh Kumar、Biswanath Das

  DOI：10.1039/c7nj02441j

  日期：——

  A novel CuI-catalyzed oxidative amidation of 2-aminophenylacetylenes leading to the formation of isatins by using open air as an oxygen source has been developed. The reaction proceeded smoothly and provided a variety of isatin derivatives in good yields. The advantages of this one-pot reaction protocol include the use of a green oxidant, low-price catalyst and facile conditions, and easy handling

  已经开发出一种新颖的CuI催化的2-氨基苯基乙炔的氧化酰胺化反应，该反应通过使用露天作为氧气源导致靛红的形成。反应进行得很顺利，并以高收率提供了各种靛红衍生物。这种一锅法反应方案的优点包括使用绿色氧化剂，价格低廉的催化剂和便利的条件，并且易于处理。
• Sulfamic acid promoted expeditious and column chromatography free synthesis of functionalized spiro [indoline-3, 7′-pyrano [3, 2-c: 5, 6-c'] dichromene]-2, 6′, 8′-trione derivatives under reflux conditions
  作者：Kajal Mal、Chhanda Mukhopadhyay

  DOI：10.1016/j.molstruc.2021.132213

  日期：2022.4

  been accomplished based on a pseudo three-component reaction between isatins and 4-hydroxycoumarin in presence of a low-cost and eco-friendly solid sulfamic acid catalyst in aqueous ethanol (1:1, v/v) under reflux condition. The significant features of this newly developed method are metal-free one pot synthesis, use of eco-friendly and cost-effective solvent and catalyst, no column chromatography involvement

  开发一个快速和绿色的协议来获取与药学相关和多样化的功能化支架，Spiro [indoline-3,7'-pyrano[3,2- c : 5,6- c ']dichromene]-2,6',8' -trione，基于靛红和 4-羟基香豆素之间的假三组分反应在低成本和环保的固体氨基磺酸催化剂存在下在乙醇水溶液（1:1，v/v）回流条件下完成. 这种新开发的方法的显着特点是无金属一锅合成，使用环保且具有成本效益的溶剂和催化剂，无需柱色谱分离产物，收率高至极好，反应介质和克数可重复使用。规模综合适用性。
• Diisobutylaluminium hydride mediated efficient synthesis of Morita–Baylis–Hilman adducts through α‐functionalization of alkyl propiolates
  作者：Sailam Sri Gogula、Ramakrishna Konakalla、Kamalaker Reddy Kamireddy、Muralidar Reddy Puchakayala、Ch. Abraham Lincoln、Venkata Subba Reddy Basireddy

  DOI：10.1002/jhet.4602

  日期：2023.3

  Generally, oxindole derivatives are biologically important molecules and valuable building blocks in organic synthesis. Herein, we report a diisobutylaluminium hydride mediated efficient one-pot synthesis of oxindole derivatives using N-substituted isatins with methyl or ethyl propiolates at lower temperature (−78°C) through Morita-Baylis-Hillman (MBH) reaction. Within a short reaction time, a wide

  通常，羟吲哚衍生物是生物学上重要的分子和有机合成中有价值的组成部分。在此，我们报道了一种二异丁基氢化铝介导的羟吲哚衍生物的高效一锅法合成，使用N-取代靛红与丙炔酸甲酯或乙酯在较低温度 (-78°C) 下通过 Morita-Baylis-Hillman (MBH) 反应。在较短的反应时间内，可以在温和的反应条件下以优异的产率轻松获得各种N-烷基或N-芳基 3-羟基羟吲哚衍生物（MBH 加合物）。
• Thiazolyl hydrazineylidenyl indolones as unique potential multitargeting broad-spectrum antimicrobial agents
  作者：Wen-Hao Zhao、Jia-He Xu、Vijai Kumar Reddy Tangadanchu、Cheng-He Zhou

  DOI：10.1016/j.ejmech.2023.115452

  日期：2023.8

  bactericidal ability, good antibiofilm activity and promising pharmacokinetic properties, but also could significantly impede the development of bacterial resistance. Preliminary exploration of antibacterial mechanism revealed that THI 6c could effectively penetrate the cell membrane of MRSA and embed DNA to form 6c‒DNA supramolecular complex and thus hinder DNA replication. Moreover, THI 6c could reduce

  致病微生物和耐药微生物的出现严重威胁着公共安全。这项工作构建了一种独特的噻唑基亚肼基吲哚酮(THIs) 来对抗全球微生物的多重耐药性。生物活性评估发现，一些目标 THIs对测试菌株显示出比临床氯霉素、诺氟沙星、头孢地尼或氟康唑更优越的抗菌效果。值得注意的是，丁基 THI 6c显示出广泛的抗菌谱，MIC 仅为 0.25–1 μg/mL。高活性的THI 6c不仅表现出低细胞毒性和溶血性、快速杀菌能力、良好的抗生物膜活性和良好的药代动力学。特性，但也可能显着阻碍细菌耐药性的发展。抗菌机制初步探索表明，THI 6c可有效穿透MRSA细胞膜嵌入DNA，形成6c-DNA超分子复合物，从而阻碍DNA复制。此外，THI6c可以降低细胞代谢活性，这可能是由于 THI6c可以靶向 MRSA 的丙酮酸激酶并干扰酶的功能。这些结果为进一步开发噻唑基亚肼基吲哚酮作为新型广谱抗菌剂提供了有力的信息。