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Squaric acid (dihydroxycyclobutenedione), the dianion of which may be regarded as a novel aromatic system, has recently become readily accessible by simple syntheses. The acidic character of squaric acid manifests itself in the formation of salts and of lower alkyl esters, which can be converted into the amides. Squaric acid dichloride shows in its reactions typical acyl chloride behavior. Condensation of squaric acid with pyrrole, phenol, and azulene derivatives yields cyclotrimethine dyes. 相似文献
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N-芳基氮氧方酸的活性羟基能够被芳伯胺取代。利用这一特性,可在方酸四碳环上引入另一不同的芳胺基,即可获得不对称芳基取代的方酰胺或异方酰胺。以乙醇等为介质,芳伯胺与7种N-芳基氮方酸反应,制得25个不对称的方酰胺和24个不对称的异方酰胺。该合成方法优点突出,反应简便有效,通用性强。 相似文献
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Charton J Charruault L Deprez-Poulain R Deprez B 《Combinatorial chemistry & high throughput screening》2008,11(4):294-303
Many natural privileged scaffolds contain a basic nitrogen atom, which often is a key element of pharmacophore and a chemically reactive centre as well. In our ongoing research program devoted to the design of targeted libraries based on acidic templates, we developed methods to convert privileged basic compounds -like natural alkaloids or drugs into acidic compounds. This conversion led to a profound alteration of the pharmacophore, without changing the overall shape and lipophilicity of the molecule. We expect such modifications to generate unexpected biological activities. Recently, we focused on derivatives of squaric acid, a vinylogous carboxylic acid. Two series were studied. First we describe a new, selective parallel synthesis of squaramic acids from a dissymmetric diester (3-tert-butoxy-4-ethoxy-cyclobut-3-en-1,2-dione). This efficient procedure avoids the synthesis of the undesired squaramides. Secondly we describe a microplate parallel synthesis (15 micromol-scale) of squaric acid hydroxamate amides from a squaric hydroxamate ester. 相似文献
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N-方酰麻黄碱配体的合成及催化前手性芳酮的不对称还原反应 总被引:2,自引:0,他引:2
方酸与醇反应成方酸二酯,后者与天然麻黄碱反应得到N-方酰麻黄碱或N-方酰双麻黄碱。单N-方酰麻黄碱与脂肪胺及硫氢化钠等反应合成了C-3位含氮和含硫的系列配体。首次将这些方酰麻黄碱配体经原位制备手性恶唑硼烷催化前手性芳酮及二酮的不对称还原反应,得到化学产率和e.e.值分别为85%-98%和52.5%-87.4%的手性仲醇。新化合物的结构已IR,^1H NMR,MS和元素分析所证实,化合物4b的晶体结构用X射线射确认。 相似文献
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L. Schneider 《Helvetica chimica acta》1968,51(1):67-74
Disazo dyes from 6-amino-1-hydroxy-naphthalene-3-sulfonic acid (J acid) were synthesized by coupling ortho-hydroxy monoazo dyes with different diazonium compounds in acid medium (dyes No 3 – 14 . A second coupling to the ortho position of the amino group was also possible with the copper complexes of o,o' -dihydroxy monoazo dyes from 8-amino-1-hydroxynaphthalene-3,6-disulfonic acid (H acid) dyes No 19 – 22 ). This is a reversal of the well known rule that the formation of disazo dyes with aminonaphthol-sulfonic acids is only practicable when an acid coupling is followed by an alkaline one. 5-Amino-1-hydroxy-naphthalene-3-sulfonic acid (M acid), which is said to form no disazo dyes, could be coupled twice with several diazonium compounds to yield disazo dyes (dyes No 24 , 26 , 27 , 29 ). 相似文献
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[reaction: see text] Condensation of squaric acid with quinaldinium salts containing electron-donating substituents gave only the semisquaraines. However, with salts possessing electronegative and electron-withdrawing groups, the squaraine dyes were isolated in quantitative yields. The semisquaraines formed undergo condensation with highly nucleophilic salts yielding the unsymmetrical squaraine dyes. These results demonstrate the role of electronic factors and provide valuable information for the design of efficient squaraine-based sensitizers that can have potential applications in photodynamic therapy. 相似文献
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Parag G. Mehta 《合成通讯》2013,43(17):2497-2502
A new procedure for the synthesis of the benzylic ester of the squaric acid is described. A first example of the reaction silyl ‘enol ether’ of the squaric acid with an electrophile in the presence of a fluoride source to give an O-alkylated product is described. 相似文献
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曾合成并研究了以1,3-双苯氨基方酸内翁盐为骨架,在苯环的2-位对称引入多甘醇醚链的双臂型方酰胺多齿配体,其中某些化合物既能作为配体对UO~2^2^+及ZγO^2^+等刚性离子配位,又能与配体NH~3发生作用,以它作为中性载体的氨选择性电极可望用于NH~3的测定。在脂肪胺的方酸内翁盐型多齿配体中,因无芳环的共轭,四碳环及其上氧之电荷状态将有所不同,这必将影响整个分子的性质。本文对这类化合物的合成进行探索,找到了行之有效的合成方法,并由此制得了九个方酰胺配体5(a~i),其中5i可作为聚酰胺等的稳定剂,其余均未见文献报道。 相似文献
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研究了环方铂三种立体异构体(SS,RS和RR)与小牛胸腺DNA的作用。差示扫描量热法(DSC)测得的数据显示出三种经合物与DNA作用的结果分别使其熔融温度下降了0.6,1.4和2.2K,有无DNA存在时三种化合物及方酸。的^13C核磁共振谱表明,当三种化合物DNA作用时,先释放出方酸根生成水铂,而后再与DNA结合。综述上述实验结果,对三种化合物与DNA的作用强度、方式及机理进行了讨论。 相似文献
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Ab Initio and Density Functional Study on the First Hyperpolarizabilities of Squaric Acid Homologues
The first hyperpolarizabilities of four squaric acid homologues: squaric acid, 1,2-dithiosquaric acid,1,2-diselenosquaric acid and 1,2-ditellurosquaric acid have been calculated using ab initio and DFT methods. The effects of equilibrium geometries, basis set and electron correlation on the first hyperpolarizabilties of these molecules were investigated. The frequency dispersion effect and solvent effect, which are essential to get reliable outputs in comparison to the experimental results, have also been explored. On the basis of these investigations, it is worthy to point out that the heavy atom effect takes effect for these squaric acid homologues. 相似文献
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Benniston AC Winstanley TP Lemmetyinen H Tkachenko NV Harrington RW Wills C 《Organic letters》2012,14(6):1374-1377
The synthesis of dyes based on a highly substituted terephthalic acid core is described, starting from readily available 2,5-dihydroxy-terephthalic acid diethyl ester. The dyes are highly colored, soluble in organic solvents and reasonably fluorescent in solution and in the solid state. The maxima for absorption and emission are around 402 and 502 nm, respectively. The fluorophores are readily cyclized to generate compounds which comprise the basic 6,13-dihydroxy-chromeno[2,3-b]xanthene-7,14-dione unit. These new derivatives are nonfluorescent. 相似文献
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Corsi DM Elst LV Muller RN van Bekkum H Peters JA 《Chemistry (Weinheim an der Bergstrasse, Germany)》2001,7(1):64-71
Magnetic resonance angiography (MRA) has put forth an impetus for the development of macromolecular GdIII complexes that have a prolonged lifetime in the vascular system. Herein, we report the synthesis and GdIII complexation of a new sugar conjugate based on inulin and the DO3A ligand (DO3A = 1,4,7,10-tetraazacyclododecan-1,4,7-triacetic acid). Two API-DO3ASQ conjugates (API = O-(aminopropyl)inulin, SQ = squaric acid = 3,4-dihydroxy-3-cyclobutene-1,2-dione) with different degrees of substitution (ds = 0.7 and ds = 1.5) were prepared from API by using the diethyl ester of squaric acid as a linking agent for the DO3A chelate. The efficacies of the resulting GdIII compounds were evaluated by investigation of their water 1H longitudinal-relaxation-rate enhancements at variable field (NMRD). A dramatic increase in relaxivity was observed in the more highly substituted conjugate (ds = 1.5); this prompted us to do a variable-temperature (17)O study in order to further characterize the relaxation parameters involved in this system. [Gd(API-DO3ASQ)] shows promising properties for application as a contrast agent for MRI. 相似文献
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双臂型方酰胺多齿配体的合成(三) 总被引:1,自引:0,他引:1
Six new multidentates, chromogenic squaraine ligands, 3 ~8 are synthesized. In butanol-toluene couple medium, o-aminophenol reacts with squaric acid to give 1, 3-bissubstituted product 2 and monosubstituted product 3. It is noteworthy that reactions of N- hydroxyethyl-(2-amino-4-chloro) aniline and N-hydroxyethyl-(4-chloro-2- nitro) aniline with squaric acid do not give isosquaramide, 1, 3- substituted derivate but squaramide, 3, 4-substituted derivates 7 and 8. 相似文献
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Ornelas C Lodescar R Durandin A Canary JW Pennell R Liebes LF Weck M 《Chemistry (Weinheim an der Bergstrasse, Germany)》2011,17(13):3619-3629
Cyanine dyes are known for their fluorescence in the near-IR (NIR) region, which is desirable for biological applications. We report the synthesis of a series of aminocyanine dyes containing terminal functional groups such as acid, azide, and cyclooctyne groups for further functionalization through, for example, click chemistry. These aminocyanine dyes can be attached to polyfunctional dendrons by copper-catalyzed azide alkyne cycloaddition (CuAAC), strain-promoted azide alkyne cycloaddition (SPAAC), peptide coupling, or direct S(NR)1 reactions. The resulting dendron-dye conjugates were obtained in high yields and displayed high chemical stability and photostability. The optical properties of the new compounds were studied by UV/Vis and fluorescence spectroscopy. All compounds show large Stokes shifts and strong fluorescence in the NIR region with high quantum yields, which are optimal properties for in vivo optical imaging. 相似文献
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Karen Aknin Marion Gauriot Jane Totobenazara Noemie Deguine Rebecca Deprez-Poulain Benoit Deprez Julie Charton 《Tetrahedron letters》2012,53(4):458-461
The 4C-Ugi reaction requires an acidic component as one of the building-blocks. We report here the first use of squaric acid for this reaction to access original symmetrical compounds. The scope and conditions of the reaction were explored. 相似文献