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Structural Modifications on Dopamine Molecules toward Polydopamine Applications 面向多巴胺应用的多巴胺分子结构改造
IF 2.8 3区 化学 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-11-07 DOI: 10.1002/ejoc.202401035
Yoonji Heo, Minseo Ji, Chae Young Ryu, Haein Kim, Isaac Choi, Sung Min Kang, Min Kim
Polydopamine (PDA) is a synthetic material synthesized through the oxidative self‐polymerization of dopamine under alkaline conditions. This material emulates the adhesive properties of mussel foot proteins, allowing the formation of robust and stable organic coatings on various surfaces. Researchers have attempted to identify and improve the surface‐coating properties of PDA by incorporating additional organic functional groups. This review explores the structural modifications of dopamine molecules at the organic chemistry level, with a focus on changes in the catechol moiety and aliphatic amines, and examines their impact on the applications of PDA. The flexibility of these modifications underscores their importance for optimizing PDA coatings for a wide range of applications.
聚多巴胺(PDA)是通过多巴胺在碱性条件下的氧化自聚合反应合成的一种合成材料。这种材料仿效了贻贝足蛋白的粘合特性,可在各种表面形成坚固稳定的有机涂层。研究人员试图通过加入更多的有机官能团来确定和改进 PDA 的表面涂层特性。本综述探讨了多巴胺分子在有机化学层面的结构修饰,重点是儿茶酚分子和脂肪胺的变化,并研究了它们对 PDA 应用的影响。这些改性的灵活性凸显了它们对于优化 PDA 涂层的重要性,使其能广泛应用于各种领域。
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引用次数: 0
An Oxidative SNH Alkylamination of 5(6,7,8)-Nitroquinoline N-Oxides in Aqueous Dioxane Medium 二氧六环水介质中 5(6,7,8)-硝基喹啉 N-氧化物的氧化 SNH 烷基化反应
IF 2.8 3区 化学 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-11-06 DOI: 10.1002/ejoc.202401060
Alexander Nikolaevich Larin, Elena Kimovna Avakyan, Oleg Demidov, Anastasia Alekseevna Borovleva, Alexander A. Zubenko, Diana Yu. Pobedinskaya, Artem Pavlovich Ermolenko, Stepan E. Kolosov, Ivan V. Borovlev
A novel and efficient method for the synthesis of 2-alkylamino and 2-dialkylamino derivatives of N-oxides of 5-, 6-, 7- and 8-nitroquinolines, which can potentially exhibit biological activity, as containing a pharmacophoric quinoline fragment, is described herein. The reactions of 5(6,7,8)-nitroquinoline N-oxides with various primary or secondary amines in the presence of potassium ferricyanide at in aqueous dioxane medium afforded the corresponding secondary and tertiary amines in moderate to excellent yields. This reaction is the first example of a Chichibabin reaction leading to the formation of 2-alkylaminoquinoline derivatives at position 2 under mild conditions. A study of the antibacterial activity of some products was carried out.
本文介绍了一种新颖高效的方法,用于合成 5、6、7 和 8-硝基喹啉 N-氧化物的 2-烷基氨基和 2-二烷基氨基衍生物,这些衍生物含有药效喹啉片段,可能具有生物活性。在铁氰化钾存在下,5(6,7,8)-硝基喹啉 N-氧化物与各种伯胺或仲胺在二噁烷水溶液介质中发生反应,得到相应的仲胺和叔胺,收率中等到极好。该反应是第一个在温和条件下通过 Chichibabin 反应在第 2 位形成 2-烷基氨基喹啉衍生物的实例。对一些产物的抗菌活性进行了研究。
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引用次数: 0
Design and Synthesis of Multipath Compact Cyclophanes for Quantum Interference Studies 设计和合成用于量子干涉研究的多径紧凑环烷
IF 2.8 3区 化学 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-11-06 DOI: 10.1002/ejoc.202400914
Salome L. Heim, Almudena Gallego, Valeria Bertozzi, Sebastiaan van der Poel, Luca Ornago, Alessandro Prescimone, Herre S. J. van der Zant, Marcel Mayor
To investigate interference phenomena and con­duc­tance properties in mechanically controlled break junctions (MCBJs), macrocycles 1 and 2 (BMCs: for BenzeneMacroCycles), containing a meta-substituted benzene moiety with solubilizing tert-butyl groups, as well as structures 3 and 4 (TMCs: for ThiopheneMacroCycles), featuring 2,5-connected 3,4-hexyl-thio­phene corners, were synthesized. Macrocycles 1 and 2 respect­ively 3 and 4 differ in the positions of the acetyl-protected sulfur anchoring groups, which impacts both, the individual transport efficiency of their parallel electronic pathways and their overall molecular wire lengths. All macrocycles were synthesized based on a series of Sonogashira cross-coupling reactions. For 3 and 4, a 2-(4-pyridin­yl)ethyl protecting group for the sulfur atoms was successful, while for macrocycles 1 and 2 the more common tert-butyl protecting group did the job. To our delight, proof-of-concept charge transport studies conducted in an MCBJ setup demon­strated the expected trends regarding improved conductance intensities for the TMCs compared to the BMCs. Furthermore, the corres­ponding molecular plateaus from the breaking experiments were in the expected length range of the S-S distances for all compounds. We also found that the overall conductance seems to follow a more complex transport mechanism than just the sum of contributions from both channels.
为了研究机械控制断裂结(MCBJ)中的干涉现象和传导特性,我们合成了含有元取代苯分子和增溶叔丁基的大环 1 和 2(BMC:代表苯大环),以及具有 2,5 连接的 3,4-hexyl-thiophene 角的结构 3 和 4(TMC:代表噻吩大环)。大环 1 和大环 2、大环 3 和大环 4 在乙酰基保护的硫锚定基团的位置上有所不同,这既影响了平行电子通路的传输效率,也影响了它们的整体分子线长度。所有大环都是通过一系列索诺伽希拉交叉偶联反应合成的。对于 3 号和 4 号大环,硫原子上的 2-(4-吡啶基)乙基保护基团取得了成功,而对于 1 号和 2 号大环,更常见的叔丁基保护基团则发挥了作用。令我们欣喜的是,在 MCBJ 设置中进行的概念验证电荷传输研究表明,与 BMC 相比,TMC 的电导强度出现了预期的改善趋势。此外,所有化合物在断裂实验中产生的相应分子高原都在 S-S 距离的预期长度范围内。我们还发现,整体电导似乎遵循一种更复杂的传输机制,而不仅仅是两个通道的贡献之和。
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引用次数: 0
NHC-Catalyzed, Microwave-Assisted and Base-Dependent Reactions of Substituted Cinnamaldehydes Towards γ-Lactones or Saturated Esters NHC 催化、微波辅助和碱依赖的取代肉桂醛与γ-内酯或饱和酯的反应
IF 2.8 3区 化学 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-11-06 DOI: 10.1002/ejoc.202401047
Victoria Magrioti, Evanthia Papadaki, Antonia Kapoti, Roza Leitourgaki, Aikaterini Vogiatzi
N-Heterocyclic carbenes (NHCs) generated from imidazolium, imidazopyridinium and imidazoquinolinium hydrochlorides in situ using base and microwave irradiation were employed as organocatalysts to yield homoenolates from cinnamaldehyde and its aryl-substituted analogs. Depending on the catalytic base either γ-lactones were prepared when the strong base tBuOK was used or the corresponding saturated ethyl 3-aryl propionates were synthesized with the milder DIPEA base. Novel imidazopyridinium and imidazoquinolinium hydrochlorides were synthesized and were compared to commercially available NHCs IMes and IDip for their catalytic activity. The optimum reaction conditions were established using IMes and the broad scope of both reactions was investigated using the 4 most efficient NHCs.
利用碱和微波辐照从咪唑鎓、咪唑吡啶鎓和咪唑喹啉鎓盐酸盐原位生成的 N-杂环碳烯(NHC)作为有机催化剂,从肉桂醛及其芳基取代的类似物中生成均烯醇酯。根据催化碱的不同,要么使用强碱 tBuOK 制备出 γ-内酯,要么使用较温和的 DIPEA 碱合成相应的饱和 3-芳基丙酸乙酯。合成了新型咪唑吡啶鎓和咪唑喹啉鎓盐酸盐,并与市售的 NHC IMes 和 IDip 进行了催化活性比较。使用 IMes 确定了最佳反应条件,并使用 4 种最有效的 NHC 研究了这两种反应的广泛范围。
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引用次数: 0
First Total Synthesis of Deinococcucin A, a Key Glycolipid Found in Cell Membranes of Extremophilic Bacteria. 嗜极细菌细胞膜中的一种关键糖脂--Deinococcucin A 的首次全合成。
IF 2.8 3区 化学 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-11-06 DOI: 10.1002/ejoc.202400879
Jonathan Martins, Abed Bil, José Kovensky, Sylvestre Toumieux, Sylvain Laclef
Deinococcucin A is a secondary metabolite isolated from a gut bacteria of carpenter ant, member of extremophilic Deinoccocus family. The structure is a glycolipid containing N-acetyl glucosamine, linked in α anomeric position to a chiral 2,3-dihydroxypropanamide moiety. We succeeded a new strategy starting directly from N-acetylglucosamine and transforming in an efficient manner an allyl group to the corresponding chiral α-hydroxyamide. Three key steps were used: the oxidation of primary amine to nitrile using TCCA, as well as its hydrolysis to the corresponding amide using palladium (II) catalyzed conditions. The synthesis was completed in only 10 steps with an overall yield of 3%.
Deinococcucin A 是一种从木匠蚁肠道细菌中分离出来的次级代谢物,木匠蚁是嗜极端细菌 Deinoccocus 家族的成员。其结构是一种含有 N-乙酰葡糖胺的糖脂,在 α 异构体位置与手性 2,3-二羟基丙酰胺分子相连。我们成功地采用了一种新策略,直接从 N-乙酰葡糖胺开始,以高效的方式将烯丙基转化为相应的手性 α-羟基酰胺。其中使用了三个关键步骤:使用 TCCA 将伯胺氧化成腈,以及在钯(II)催化条件下将其水解成相应的酰胺。合成只需 10 个步骤即可完成,总产率为 3%。
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引用次数: 0
Photooxidation of Polystyrene into High-Value Chemicals 将聚苯乙烯光氧化成高价值化学品
IF 2.8 3区 化学 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-11-05 DOI: 10.1002/ejoc.202401109
Shusheng Jiang, Yunhan Chen, Yahao Huang, Peng Hu
Plastics play a crucial role in the survival and advancement of human civilization. However, the increasing challenge of plastic pollution presents significant obstacles. Disposal methods such as incineration and landfilling result in substantial resource wastage and pose potential environmental hazards. The slow progress in recycling and reusing waste plastics hinders their industrial application and effective response to environmental crises. Photocatalysis offers promising solutions for the future of plastic recycling, particularly with the recent increase in photocatalytic degradation methods for polystyrene (PS). This review provides a comprehensive overview of the latest advancements in the photooxidation of PS into high-value chemicals.
塑料在人类文明的生存和进步中发挥着至关重要的作用。然而,日益严峻的塑料污染挑战带来了巨大障碍。焚烧和填埋等处理方法造成大量资源浪费,并对环境造成潜在危害。废塑料的回收和再利用进展缓慢,阻碍了其工业应用和有效应对环境危机。光催化技术为未来的塑料回收利用提供了前景广阔的解决方案,尤其是最近聚苯乙烯(PS)的光催化降解方法不断增加。本综述全面概述了将聚苯乙烯光氧化成高价值化学品的最新进展。
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引用次数: 0
Palladium-Catalyzed Domino Synthesis of Sulfone-Containing 1,3-Enynes from Simple Alkynes and Sulfonyl Iodides 钯催化的由简单炔烃和磺酰基碘化物合成含砜 1,3-Enynes 的多米诺反应
IF 2.8 3区 化学 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-11-05 DOI: 10.1002/ejoc.202401028
Jing Wang, Jianwei Wang, Jun Ying
A palladium-catalyzed domino radical sulfonylation and alkynylation of simple alkynes has been developed for the rapid construction of privileged scaffolds containing sulfone and 1,3-enyne motifs. The reaction of sulfonyl iodide with simple alkynes proceeded smoothly under mild conditions to afford a variety of sulfone-containing 1,3-enynes in good yields and with excellent selectivities.
我们开发了一种钯催化的多米诺自由基磺酰化和简单炔烃的炔烃化方法,用于快速构建含有砜和 1,3-炔基团的特异性支架。磺酰基碘与简单炔烃的反应在温和的条件下顺利进行,以良好的产率和优异的选择性得到了多种含砜的 1,3-炔烃。
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引用次数: 0
Synthesis, Structure, Spectral and Redox Properties of Phenoxazine Embedded Heteroporphyrins 嵌入吩嗪的杂卟啉的合成、结构、光谱和氧化还原特性
IF 2.8 3区 化学 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-11-05 DOI: 10.1002/ejoc.202401068
Neha Tripathi, Mangalampalli Ravikanth
A series of phenoxazine embedded heteroporphyrins containing one phenoxazine, two pyrroles and one heterocycle, such as furan, thiophene, selenophene and telluorophene, connected through four meso carbon atoms were synthesized by condensing one equivalent of phenoxazine-based tripyrrane with one equivalent of the appropriate 2,5-bis(hydroxymethyl-p-tolyl) heterocycle under acid-catalyzed conditions, and their structure, spectral and electrochemical properties were compared with those of previously reported phenothiazine embedded heteroporphyrins. The X-ray crystal structure of the phenoxazine embedded selenoporphyrin revealed that the selenophene ring, which is opposite phenoxazine moiety, points outward from the macrocyclic core, and the phenoxazine unit deviated by an angle of 39.47° from the mean plane defined by the four meso carbons atoms. The replacement of the phenothiazine unit in phenothiazine embedded heteroporphyrins with a phenoxazine unit led to significant alteration of the electronic properties of the macrocycles, as reflected in their spectral and electrochemical properties. The absorption spectra of phenoxazine embedded heteroporphyrins showed bathochromically shifted absorption bands, hypsochromically shifted fluorescence bands with decent quantum yields, more facile oxidation and more difficult reduction as compared to the corresponding phenothiazine embedded heteroporphyrins. DFT and TD-DFT studies were in support of the experimental observations.
在酸催化条件下,将一个等效的吩嗪基三吡喃与一个等效的适当的 2.5-双(羟甲基-对甲苯基)杂环缩合,合成了一系列含有一个吩嗪、两个吡咯和一个杂环(如呋喃、噻吩、硒吩和碲吩)的吩嗪内嵌杂卟啉,并将它们的结构、光谱和电化学性质与之前报道的吩噻嗪内嵌杂卟啉进行了比较、在酸催化条件下,将一个等量的吩嗪基三吡喃与一个等量的适当的 2、5-双(羟甲基-对甲苯基)杂环缩合合成了吩嗪基三吡喃和碲吩,并将它们的结构、光谱和电化学性质与之前报道的吩噻嗪嵌入杂卟啉进行了比较。嵌入吩噁嗪的硒卟啉的 X 射线晶体结构显示,与吩噁嗪分子相对的硒吩环指向大环核心的外侧,吩噁嗪单元与四个中碳原子定义的平均平面偏离 39.47° 角。用吩噁嗪单元取代吩噻嗪嵌入杂卟啉中的吩噻嗪单元会显著改变大环的电子特性,这反映在它们的光谱和电化学特性上。与相应的吩噻嗪内嵌杂卟啉相比,吩嗪内嵌杂卟啉的吸收光谱显示了浴色偏移的吸收带和次浴色偏移的荧光带,量子产率较高,更容易氧化和更难还原。DFT 和 TD-DFT 研究证实了实验观察结果。
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引用次数: 0
Palladium-Catalyzed C4,C5-Diarylation of Isoxazole-3-carboxylate by Double C–H Bond Functionalization 钯催化双 C-H 键官能化异恶唑-3-羧酸酯的 C4、C5-二芳基化反应
IF 2.8 3区 化学 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-11-04 DOI: 10.1002/ejoc.202401036
Rabeb Ben Romdhane, Linhao Liu, Ridha Ben Salem, Henri Doucet
The Pd-catalyzed C4-arylation of 3,5-disubstituted isoxazoles via C-H bond functionalization has been largely described. By contrast, the reactivity of isoxazoles in C-H bond functionalization with both unsubstituted C4 and C5 positions remains largely unexplored. Herein, we report on the reactivity in Pd-catalyzed double C-H bond arylation of an isoxazole with unsubstituted C4 and C5 positions. Conditions for the palladium-catalyzed direct C4,C5-diarylation of ethyl isoxazole-3-carboxylate using aryl bromides as the aryl source are reported. This procedure tolerates several useful substituents on the aryl bromide such as nitrile, acetyl, formyl, benzoyl, alkoxycarbonyl, chloro, fluoro, trifluoromethyl, trifluoromethoxy, cyanomethyl,tertbutyl and methoxy at para- and meta-positions. Conversely, with ortho-substituted aryl bromides, mixtures of mono- and di-arylated isoxazoles were generally obtained. This methodology provides a simple one pot access to a wide variety of C4,C5-diarylated isoxazoles from commercially available substrates allowing to modify easily their biological properties.
通过 C-H 键官能化,Pd 催化 3,5 二甲基异噁唑的 C4 芳基化反应已被广泛描述。相比之下,异噁唑与未取代的 C4 和 C5 位的 C-H 键官能化反应性在很大程度上仍未得到探索。在此,我们报告了钯催化未取代 C4 和 C5 位的异噁唑双 C-H 键芳基化的反应性。报告了以芳基溴化物为芳基源,钯催化异噁唑-3-羧酸乙酯直接发生 C4、C5-二芳基化反应的条件。该过程可容忍芳基溴上的几个有用取代基,如腈、乙酰基、甲酰基、苯甲酰基、烷氧羰基、氯、氟、三氟甲基、三氟甲氧基、氰甲基、叔丁基和对位和偏位的甲氧基。相反,使用正交取代的芳基溴,通常会得到单芳基和二芳基异噁唑的混合物。这种方法提供了一种简单的一锅式方法,可从市售底物中获得多种 C4、C5-二芳基化异噁唑,从而轻松改变它们的生物特性。
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引用次数: 0
Chiral Secondary Phosphine Oxide Ligands in Asymmetric Ni–Al Bimetallic Catalysis 不对称 Ni-Al 双金属催化中的手性仲膦氧化物配体
IF 2.8 3区 化学 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-11-02 DOI: 10.1002/ejoc.202401000
Mengying Xu, Weiwei Xu, Mengchun Ye
Ligands play a key role in asymmetric transition-metal catalysis. Among reported chiral ligands, readily available and air-stable secondary phosphine oxide ligands are unique and have aroused wide interest in Ni–Al bimetallic catalysis, since they can act as bifunctional ligands to ligate two metals for stronger bimetallic synergism, greatly enhancing reactivity and selectivity. Hence, in this mini review we will focus on secondary phosphine oxides and their applications in asymmetric Ni-Al bimetallic catalysis.
配体在不对称过渡金属催化中起着关键作用。在已报道的手性配体中,易于获得且在空气中稳定的仲膦氧化物配体是独一无二的,并在镍铝双金属催化中引起了广泛的兴趣,因为它们可以作为双功能配体连接两种金属,从而产生更强的双金属协同作用,大大提高反应活性和选择性。因此,在这篇小型综述中,我们将重点介绍仲膦氧化物及其在不对称镍铝双金属催化中的应用。
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引用次数: 0
期刊
European Journal of Organic Chemistry
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