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Search for "solubility" in Full Text gives 944 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Recent advances in amidyl radical-mediated photocatalytic direct intermolecular hydrogen atom transfer
Beilstein J. Org. Chem. 2025, 21, 1306–1323, doi:10.3762/bjoc.21.100
- structurally diversified target molecules 65–68 under optimized reaction conditions. In these cases, the high polarity of the radical intermediates of CF3CH2OH and 4-methylbenzonitrile, combined with the poor solubility of adamantane, may explain the possible reasons behind the reaction process [91]. Amidyl
Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents
Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98
Optimized synthesis of aroyl-S,N-ketene acetals by omission of solubilizing alcohol cosolvents
Beilstein J. Org. Chem. 2025, 21, 1201–1206, doi:10.3762/bjoc.21.97
- of an amine base in a binary 1,4-dioxane/ethanol mixture. Ethanol was used as a cosolvent to ensure solubility of the polar intermediate according to the mechanistic rationale (Scheme 2) [5][6]. Although, a broad scope of diversely substituted (hetero)aroyl-S,N-ketene acetals 8 was obtained (111
Selective monoformylation of naphthalene-fused propellanes for methylene-alternating copolymers
Beilstein J. Org. Chem. 2025, 21, 1183–1191, doi:10.3762/bjoc.21.95
- followed by acid-mediated condensation. The linear copolymers show good solubility and carbon dioxide adsorption. Keywords: alternating copolymer; building block; formylation; gas adsorption; propellane; Introduction Combination of sp2- and sp3-hybridized atoms in core π-skeletons [1][2][3] is a key to
- go beyond common organic functional materials composed of rigid π-conjugated planes and flexible peripheral substituents. Because larger π-conjugated planes mostly display low solubility and dense packing due to the π–π stacking and CH–π interactions, surrounding alkyl and other flexible moieties are
- widely adopted to improve the solubility and modulate the molecular assemblies [4][5][6][7][8][9]. By contrast, the presence of sp3-hybridized atoms in core π-skeletons can lead to three-dimensional (3D) structures with appropriate rigidity, thereby giving macrocyclic arenes [10][11], molecule-based
Gold extraction at the molecular level using α- and β-cyclodextrins
Beilstein J. Org. Chem. 2025, 21, 1116–1125, doi:10.3762/bjoc.21.89
- that resembles a truncated cone. Secondary hydroxy groups of the glucose residues are directed towards the wider rim of the cone, and primary hydroxy groups, bound to C6, face the narrower rim, which overall conveys them with good aqueous solubility. The inner cavity of the cone is, in turn, lined with
- protons, which makes it sufficiently hydrophobic to host apolar guest molecules, forming particular adducts called inclusion compounds. One obvious consequence of inclusion is increased solubility, with another important action being the protection of the included guests against degradation from light
- that contributes to the overall aqueous solubility and stability of AuCl4−. The precipitation method, according to the authors, is postulated to involve acid hydrolysis of the acetal group of thiolated β-CD to form a reactive aldehyde that takes part in the reduction of the Au3+ cations that get bound
Biobased carbon dots as photoreductants – an investigation by using triarylsulfonium salts
Beilstein J. Org. Chem. 2025, 21, 1024–1030, doi:10.3762/bjoc.21.84
- solution was examined, for solubility reasons. a) CDs-mediated 1,2-difunctionalization of alkenes by alkyl halides R–Y and b) light-driven reduction of triarylsulfonium salts in the presence of CDs. Carbon dots tested in this project and their main (photo)physical characteristics. Emission parameters for
Recent advances in controllable/divergent synthesis
Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73
- in chloroform or dichloromethane (DCM), converting entirely into the thermodynamically stable [1 + 1] isomer 39. This work demonstrates a solvent-driven approach for dynamically interconverting macrocycle sizes, governed by thermodynamic stability and solubility differences. In the same year, Chauhan
Unraveling cooperative interactions between complexed ions in dual-host strategy for cesium salt separation
Beilstein J. Org. Chem. 2025, 21, 845–853, doi:10.3762/bjoc.21.68
- extraction efficiency was seen for the dual-host strategy. Additionally, the use of 18-crown-6 alone displays better extraction efficiency than that of hexaurea receptor (Table 1), which is attributed to the relatively poor solubility of the hexaurea receptor in CHCl3. For cesium salts with various oxyanions
Substituent effects in N-acetylated phenylazopyrazole photoswitches
Beilstein J. Org. Chem. 2025, 21, 830–838, doi:10.3762/bjoc.21.66
- classical azobenzenes. Heterocyclic rings offer, for example, enhanced polarity, electron pairs for metal coordination [27], better water-solubility, and variable pKa [28][29]. Special attention has been given to 5-membered N-heterocyclic azobenzenes, which not only maintain the azobenzenes properties but
Recent advances in the electrochemical synthesis of organophosphorus compounds
Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61
- have shown that the choice of solvent significantly impacts the reaction. CH₃CN exhibits better than CH₃OH, with a wider electrochemical window and better reactant solubility. When the reaction was conducted in CH₃CN using n-Bu₄NPF₆ and n-Bu₄NBF₄ as electrolytes but without iodide salt and in the
- were obtained using platinum electrodes as the anode and cathode (Scheme 25). Studies showed that CH₃CN performed better than CH₃OH due to its wider electrochemical window and better solubility. The results indicated that the electronic properties of substituents had no significant effect on the yield
- ). Although using other solvents improved the solubility, it reduced the reaction yield. Ammonium thiocyanate is used as a sulfur source in the presence of DBU as a base and n-Bu4NBF4 as an electrolyte. When electron-donating groups were present at the C2-benzene ring, the reaction yield was higher than when
Orthogonal photoswitching of heterobivalent azobenzene glycoclusters: the effect of glycoligand orientation in bacterial adhesion
Beilstein J. Org. Chem. 2025, 21, 736–748, doi:10.3762/bjoc.21.57
- α-ᴅ-mannoside (MeMan) measured on the same plate as reference. This leads to relative inhibitory potencies, so-called RIP values. Because of limited water solubility, the samples had to be dissolved in DMSO and therefore, the effect of pure DMSO was also tested in every individual assay (cf
- , Figures S13–S16), the analysis of the testing results shows that determination of the inhibitory potencies of the various isomers is indeed valid in spite of the limited water solubility of the samples. Looking over the measured inhibitory potentials, it can be concluded that (i) the isomeric state of the
- like glycoclusters 1 and 2 are capable of many conformational alternatives and therefore, the control of molecular shape by photoisomerization of azobenzene linkers has its limitations. In addition, water solubility requires improvement. Furthermore, our study, combining synthesis, analysis of
Synthesis of HBC fluorophores with an electrophilic handle for covalent attachment to Pepper RNA
Beilstein J. Org. Chem. 2025, 21, 727–735, doi:10.3762/bjoc.21.56
- better solubility in the reaction buffer and did not require DMSO as co-solvent, making it a very promising candidate for in vivo applications. To complete the study, and given that the mesyloxy group has shown superior efficacy over all other functional groups tested for Pepper alkylation, we
- fluorophores also exhibited favorable solubility compared to the other functionalizations which is a critical aspect for applications in the cell. We also note that primary alkyl halides, and in particular, the mesyloxy alkyl handles presented here, are relatively underexplored for covalent labeling of nucleic
Acyclic cucurbit[n]uril bearing alkyl sulfate ionic groups
Beilstein J. Org. Chem. 2025, 21, 717–726, doi:10.3762/bjoc.21.55
- spectroscopic characterization of C1 along with determination of its inherent aqueous solubility and self-association properties. Next, we present the X-ray crystal structure of C1 as its C1·Me6CHDA complex. Subsequently, we describe a qualitative investigation of C1·guest and M1·guest complexation by 1H NMR
- shows an ion at m/z = 751.13 which corresponds to [C1 − 2Na]2−. Inherent aqueous solubility of C1 After having firmly established the structure of C1 we decided to determine its inherent aqueous solubility. For this purpose, we added an excess of solid C1 to D2O and stirred the solution at room
- spectrum using a delay time between pulses of 20 seconds to ensure accurate integration. The inherent aqueous solubility of C1 was determined to be 3.97 mM by comparison of the integrals for Ha of C1 with that of the CH3-resonance for dimethyl malonic acid (Figure S5 in Supporting Information File 1
Origami with small molecules: exploiting the C–F bond as a conformational tool
Beilstein J. Org. Chem. 2025, 21, 680–716, doi:10.3762/bjoc.21.54
- valuable property in the context of drug design, because chameleonic fluorinated molecules such as compounds 2 and 3 might be expected to pass more easily through cell membranes, a manoeuvre which requires some level of solubility in both aqueous and organic environments. Another consequence of introducing
- be altered, too [44]. For example, consider compounds 26 and 27 (Figure 4), which are fluorinated analogues of the multiple sclerosis drug gilenya (25) [45]. The syn,anti-fluorinated stereoisomer 26 has a much higher water solubility than gilenya (25), attributable to the presence of new polar bonds
- in 26 (although the different alkyl chain lengths in 25 and 26 should also be acknowledged). Notably, the all-syn fluorinated stereoisomer 27 displays a further increase in water solubility, even compared to the syn,anti-stereoisomer 26, highlighting the dramatic impact that a seemingly minor
Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra
Beilstein J. Org. Chem. 2025, 21, 670–679, doi:10.3762/bjoc.21.53
- was obtained by a Migita–Kosugi–Stille coupling between bromophenanthrene 15 and (E)-1,2-bis(tributylstannyl)ethene to afford diarylethene 18 followed by Mallory photoreaction. The obtained intermediate 18 contained residual palladium and isolation was not successful due to its poor solubility in
Entry to 2-aminoprolines via electrochemical decarboxylative amidation of N‑acetylamino malonic acid monoesters
Beilstein J. Org. Chem. 2025, 21, 630–638, doi:10.3762/bjoc.21.50
- amount of water was reduced from 33% to 17% (Table 1, entry 8 vs entry 7), an observation that might be useful for substrates of low aqueous solubility. However, further reduction of water amount to 5 equivalents completely inhibited the anodic oxidation of 9a, and only traces of the desired 6a were
Photocatalyzed elaboration of antibody-based bioconjugates
Beilstein J. Org. Chem. 2025, 21, 616–629, doi:10.3762/bjoc.21.49
- facilitated a site-specific covalent linkage to the antibody, resulting in the formation of a DAR 2 ADC precursor. For their ADC design strategy, the group selected a polyethylene glycol (PEG) linker, as it enhances the water solubility of the ADC, while the payload consists of the cytotoxic agent DM1, which
Formaldehyde surrogates in multicomponent reactions
Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45
- carbon atom, due to the readiness for losing a water molecule. Formaldehyde is commonly used in its polymeric form (paraformaldehyde) or in a 37% aqueous solution (formalin). The exceptional solubility of formaldehyde in water or biobased solvents, such as ethanol and glycerol, enhances the feasibility
- ]. They argued that organic bases such as DBU are superior than inorganic bases in improving the yields, probably because of the low solubility of the last ones in the reaction system. In the same way, other bases such as DABCO [64], DBU [66], and TMG (1,1,3,3-tetramethylguanidine) [65][67] were shown to
- well for a wide variety of solvents and under mild basic conditions, since the solubility of the reagents and ease of product isolation are the factors that govern the choice. Sisko et al. used DMF/K2CO3 as the best conditions to carry out the cycloaddition of a wide variety of amines, aldehydes, and
Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles
Beilstein J. Org. Chem. 2025, 21, 556–563, doi:10.3762/bjoc.21.44
- conditions and the obtained results are summarized in Table 1. It should be mentioned that all experiments were carried out at reflux due to low solubility of the starting compound 1a in all used solvents. At first, we carried out the process under conditions developed above for the synthesis of enamines 4
Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction
Beilstein J. Org. Chem. 2025, 21, 490–499, doi:10.3762/bjoc.21.36
- azobenzene is that the switching efficiency decreases sharply with increasing water content in the solvent. In a recently published paper, we reported that replacing one CH2 group in the bridge with NCOCH3 not only confers intrinsic water solubility, but also largely eliminates the problem of reduced
- ]. Moreover, the parent diazocine is insoluble in water (precipitation in water/DMSO > 9:1). Substitution with polar substituents such as CH2NH2 provides water solubility, however, it does not restore the high Z → E conversion rates of the parent system in organic solvents, which is a disadvantage, since
- biochemical reactions usually take place in aqueous environments [13]. The substitution of one CH2 group in the CH2CH2 bridge by N–C(=O)–CH3 leads to an intrinsic water solubility of the N-acetyl diazocine 1 (Figure 1) [3]. Furthermore the photoconversion of 1 shows no significant drop in pure water in
Synthesis of electrophile-tethered preQ1 analogs for covalent attachment to preQ1 RNA
Beilstein J. Org. Chem. 2025, 21, 483–489, doi:10.3762/bjoc.21.35
- derivatives have been reported [22][23][24][25][26]. Among these reports, various silylation and protection strategies have been employed to address the poor solubility of preQ1 (and analogs) in organic solvents [9][22][23][25][26][27][28][29]. Herein, we report an optimized three-step protocol, free of
- -step synthesis of O6-methyl preQ1 (16, m6preQ1) [28]. The direct reduction of the precursor O6-methyl preQ0 (15, m6preQ0) was possible, eliminating the need for the previously introduced protection/solubility concept, which shortened the synthetic route to only four steps (Supporting Information File 1
Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions
Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33
- simplifies experimental procedures. Moreover, it often leads to shorter reaction times [43][44] and can overcome solubility limitations [45]. Similar to the effect of photons in light-mediated synthesis, mechanical forces generated during ball milling can induce unconventional reaction pathways [46] enabling
Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages
Beilstein J. Org. Chem. 2025, 21, 421–443, doi:10.3762/bjoc.21.30
- self-directing and self-correcting, and the term “self-assembly” [290][291][292] often used [286][293][294][295][296]. Products can be thermodynamic or kinetic, but are often isolated by precipitation due to low solubility [297], though many have useful solubility [288][298]. Since POCs typically have
- the past few years [20][70][235][315], and true organocatalysis is exceedingly rare [316]. Instead, catalytic systems tend to be composed of cavities that increase substrate solubility [317], or host nanoparticles [318][319][320][321][322][323][324][325][326], metals [44][327][328], photoactive groups
- , which can act as an oxidation catalyst (Figure 7C) [44]. The long-standing challenges of synthesis, stability, solubility and internal functionalization are beginning to be tackled, and the remainder of this Perspective will discuss specifics of these hard-earned advances and the opportunities they
Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones
Beilstein J. Org. Chem. 2025, 21, 358–368, doi:10.3762/bjoc.21.26
- represent molecular switches of optical and fluorescent properties under sequential addition of CN− and Hg2+ ions and the transformation cycle presented in Scheme 3 can be repeated at least 5–6 times. The resulting compounds 7b and 8a,b have extremely low water solubility, which makes it impossible to
- prepare concentrations sufficient for studying cellular cytotoxicity. In this regard, 1,3-tropolone 7a, which has an acceptable level of solubility in water, was used for biological testing. The in vitro cytotoxic activity was investigated with A431 skin cancer and H1299 lung cancer cell lines. A standard
Synthesis of disulfides and 3-sulfenylchromones from sodium sulfinates catalyzed by TBAI
Beilstein J. Org. Chem. 2025, 21, 253–261, doi:10.3762/bjoc.21.17
- been further decreased, in the end, 0.5 mL of DMF was used because of the solubility of the reagents. Increasing the amount of catalyst to 20 mol % resulted in a significant increase in the yield, but further increases did not significantly change the yield (Table 1, entries 14 and 15). A decrease in
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