Category: Benzisoxazole

Name: cis-Cyclohexane-1,2-dicarboxylic acid. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: cis-Cyclohexane-1,2-dicarboxylic acid, is researched, Molecular C8H12O4, CAS is 610-09-3, about Organic ligand binding by a hydrophobic cavity in a designed tetrameric coiled-coil protein. Author is Mizuno, Toshihisa; Hasegawa, Chinatsu; Tanabe, Yoichi; Hamajima, Kenta; Muto, Takashi; Nishi, Yoshinori; Oda, Masayuki; Kobayashi, Yuji; Tanaka, Toshiki.

The design and characterization of a hydrophobic cavity in de novo designed proteins provides a wide range of information about the functions of de novo proteins. We designed a de novo tetrameric coiled-coil protein with a hydrophobic pocketlike cavity. Tetrameric coiled coils with hydrophobic cavities have previously been reported. By replacing one Leu residue at the a position with Ala, hydrophobic cavities that did not flatten out due to loose peptide chains were reliably created. To perform a detailed examination of the ligand-binding characteristics of the cavities, we originally designed two other coiled-coil proteins: AM2, with eight Ala substitutions at the adjacent a and d positions at the center of a bundled structure, and AM2W, with one Trp and seven Ala substitutions at the same positions. To increase the association of the helical peptides, each helical peptide was connected with flexible linkers, which resulted in a single peptide chain. These proteins exhibited CD spectra corresponding to superhelical structures, despite weakened hydrophobic packing. AM2W exhibited binding affinity for size-complementary organic compounds The dissociation constants, Kd, of AM2W were 220 nM for adamantane, 81 μM for 1-adamantanol, and 294 μM for 1-adamantane acetic acid, as measured by fluorescence titration analyses. Although it was contrary to expectations, AM2 did not exhibit any binding affinity, probably due to structural defects around the designed hydrophobic cavity. Interestingly, AM2W exhibited incremental structure stability through ligand binding. Plugging of structural defects with organic ligands would be expected to facilitate protein folding.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-Furoic hydrazide(SMILESS: O=C(C1=CC=CO1)NN,cas:3326-71-4) is researched.SDS of cas: 39901-94-5. The article 《Systematic approach of chromone skeleton for detecting Mg2+, ion: Applications for sustainable cytotoxicity and cell imaging possibilities》 in relation to this compound, is published in Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy. Let’s take a look at the latest research on this compound (cas:3326-71-4).

The systematic studies of chromone appended novel chemosensors, favored to Mg2+ ion detection, these were analyzed and characterized by different spectroscopic techniques such as NMR, mass spectroscopy, FTIR and optical techniques. The binding demeanor of the ligands was executed with the library of metal ions and shown the good coordination with Mg2+ ion to the ligand′s cavity. Both ligands demonstrated good binding behavior with Mg2+ ion. The ligands represented 1: 1 stoichiometry with Mg2+ ions through Job′s plot. The low limit of detection of Mg2+ ion was determined as 2.56 × 10-6 and 1.28 × 10-6 for La and Lb, resp. No interference was occurred in Inference study by foreign metal ions that supported the specific detection of Mg2+ ion among the other metal ions. Further, the cytotoxicity assay test of these chromone appended ligands revealed that both ligands and their resp. compound with Mg2+ ion shown negligible toxicity with HeLa cancer cell line. Further, due to the fluorescence properties of the ligands, with or without Mg2+ ion was successfully tested in bioimaging experiment of HeLa cancer cell lines and found that ligands with Mg2+ ions represented good imaging with HeLa cancer cell.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 3326-71-4, is researched, Molecular C5H6N2O2, about Catalyst-free, aza-Michael polymerization of hydrazides: polymerizability, kinetics, and mechanistic origin of an α-effect, the main research direction is aza Michael polymerization divinylsulfone diacrylate hydrazide alpha effect.SDS of cas: 3326-71-4.

Despite the powerful nature of the aza-Michael reaction for generating C-N linkages and bioactive moieties, the bis-Michael addition of 1° amines remains ineffective for the synthesis of functional, step-growth polymers due to the drastic reduction in reactivity of the resulting 2° amine mono-addition adduct. In this study, a wide range of com. hydrazides are shown to effectively undergo the bis-Michael reaction with divinyl sulfone (DVS) and 1,6-hexanediol diacrylate (HDA) under catalyst-free, thermal conditions to afford moderate to high mol. weight polymers with Mn = 3.8-34.5 kg mol-1. The hydrazide-Michael reactions exhibit two distinctive, conversion-dependent kinetic regimes that are 2nd-order overall, in contrast to the 3rd-order nature of amines previously reported. The mono-addition rate constant was found to be 37-fold greater than that of the bis-addition at 80°C for the reaction between benzhydrazide and DVS. A significant majority (12 of 15) of the hydrazide derivatives used here show excellent bis-Michael reactivity and achieve >97% conversions after 5 days. This behavior is consistent with calculations that show minimal variance of electron d. on the N-nucleophile among the derivatives studied. Reactivity differences between hydrazides and hexylamine are also explored. Overall, the difference in reactivity between hydrazides and amines is attributed to the adjacent nitrogen atom in hydrazides that acts as an efficient hydrogen-bond donor that facilitates intramol. proton-transfer following the formation of the zwitterion intermediate. This effect not only activates the Michael acceptor but also coordinates with addnl. Michael acceptors to form an intermol. reactant complex.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Khimiya Geterotsiklicheskikh Soedinenii called Chlorination of tetrahydrofuran-2-carboxylic acid esters, Author is Zhuk, R. A.; Berzina, A.; Silina, V.; Liepins, E.; Giller, S. A., which mentions a compound: 37443-42-8, SMILESS is O=C(C1OCCC1)OC, Molecular C6H10O3, Application of 37443-42-8.

Photochem. chlorination of Me tetrahydro-2-furancarboxylate in CCl4 at -15 to -20° gave the chlorofurancarboxylate I and small amounts of the dihydrofuran II (8%) and Me 2-furancarboxylate (2%). Et tetrahydro-2-furancarboxylate was similarly chlorinated. The by-products were formed by dehydrochlorination of intermediate x-chlorination products.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Royes, Jordi; Ni, Shaofei; Farre, Albert; La Cascia, Enrico; Carbo, Jorge J.; Cuenca, Ana B.; Maseras, Feliu; Fernandez, Elena published the article 《Copper-Catalyzed Borylative Ring Closing C-C Coupling toward Spiro- and Dispiroheterocycles》. Keywords: copper catalyst borylative ring closing coupling spiro dispiroheterocycle mechanism; crystal structure mol spiroheterocyclic pendant methylene boronate preparation optimized.They researched the compound: Methyl tetrahydrofuran-2-carboxylate( cas:37443-42-8 ).Application In Synthesis of Methyl tetrahydrofuran-2-carboxylate. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:37443-42-8) here.

The synthesis of spiroheterocyclic structures with a pendant methylene boronate substituent has been accomplished to promote further functionalization. A Cu-catalyzed borylative ring closing C-C coupling of an alkenyl halide is the key step toward the synthesis of [m.n]-spirocycles (m,n = 3-5). Computational studies on the mechanism reproduced all the exptl. trends and explain the enhanced reactivity of systems leading to strained smaller rings. The optimized protocol also gives access to dispirocycle scaffolds, fully characterized by x-ray diffraction.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 3326-71-4, is researched, SMILESS is O=C(C1=CC=CO1)NN, Molecular C5H6N2O2Journal, Article, Luminescence called A highly selective aggregation-induced emission fluorogen for sensitive detection of Al3+ in living cells, Author is Xie, Ya; Li, Xueming; Yan, Liqiang; Li, Jianping, the main research direction is A549 cell aggregation induced emission fluorogen aluminum; AIE; Al3+; Schiff’s base; coumarin; fluorescence probe.Computed Properties of C5H6N2O2.

A Schiff’s base derivative was synthesized using a condensation reaction between 8-formyl-7-hydroxy-4-methylcoumarin and furan-2-carbohydrazide that produced marked aggregation-induced emission and had excellent ability to specifically recognize aluminum ions (Al3+). This compound displayed faint fluorescence in the benign solvent DMF, and exhibited obvious green fluorescence following addition of specific amounts of water. Moreover, it exhibited strong blue fluorescence after combination with Al3+ even in the presence of other interfering ions. These exptl. results demonstrated that this derivative could be used as a fluorescence probe for Al3+. The advantages, including significant fluorescence change, high selectivity and sensitivity, and fast response, meant that this probe could be used both to detect Al3+ in water samples and for fluorescence imaging in living cells.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Photochemical transformations. XI. Isomerization of 1,3-cyclooctadiene》. Authors are Dauben, William G.; Cargill, Robert L..The article about the compound:cis-Cyclohexane-1,2-dicarboxylic acidcas:610-09-3,SMILESS:O=C([C@H]1[C@@H](C(O)=O)CCCC1)O).Reference of cis-Cyclohexane-1,2-dicarboxylic acid. Through the article, more information about this compound (cas:610-09-3) is conveyed.

cf. CA 54, 22718a. Com. 1,3-cyclooctadiene (I, n2D0 1.4940, λ 228 mμ (ε 5470, alc.), 22.1 g.) in 2 l. dry Et2O irradiated 200 hrs. with a Hanovia high pressure Hg arc lamp, internal probe, type L with magnetic stirring (He atm.), the progress of irradiation followed by ultraviolet spectroscopy to disappearance of I, the Et2O evaporated at 40-50° through a 1 ft. Vigreux column, and the yellow residue distilled through a Nester-Faust 2 ft. spinning band column gave 36-41% bicyclo[4.2.0]oct-7-ene (II), C8H12, b. 131-2°, n2D0 1.4720, λ205 mμ (ε 700, alc.), nuclear magnetic resonance singlets at 4.04 and complex multiplets at 7.21, 8.47 τ, infrared spectrum identical with that of material prepared from cyclooctatetraene dibromide. NaIO4 (9.78 millimoles), 0.16 millimole KMnO4, and 0.37 millimole K2CO3 in 200 ml. H2O stirred 25 hrs. at 25° with 1.03 millimoles II, the mixture acidified with 15% H2SO4, extracted 20 hrs. with Et2O, the dried extract evaporated, and the residue triturated with petr. ether gave 105 mg. solid, recrystallized from H2O and from Et2O-petr. ether to give cis-1,2-cyclohexanedicarboxylic acid, m. 197.5-8.0°. At no time was the typical spectrum of 1,3,5-hexatriene detected in the ultraviolet absorption spectrum of the irradiated solution

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

HPLC of Formula: 610-09-3. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: cis-Cyclohexane-1,2-dicarboxylic acid, is researched, Molecular C8H12O4, CAS is 610-09-3, about Comparison of aromatic and aliphatic dicarboxylic acid in reactivity using hydrogen-isotope exchange reaction in a gas-solid system. Author is Imaizumi, Hiroshi; Muramatsu, Kazuo.

The hydrogen-isotope exchange reaction between aromatic (alicyclic, or normal chain aliphatic) dicarboxylic acid (solid) and HTO vapor was observed at 40 °C ∼ 80° to reveal the reactivity of the material having the same two functional groups. The A””-McKay plot method was used to determine its rate constant From the rate constants thus determined, the following three findings have been clarified in the reaction. (1) The reactivity of aromatic dicarboxylic acid is similar to that of normal chain aliphatic dicarboxylic acid, and is greater than that of alicyclic acid. (2) With regard to 1,2- or 1,4-cyclohexanedicarboxylic acid, cis-isomer is similar to trans-isomer in reactivity. (3) The reactivity of isophthalic acid is larger than that of benzoic acid, and seems to follow the Hammett LFER.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Related Products of 3326-71-4. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Furoic hydrazide, is researched, Molecular C5H6N2O2, CAS is 3326-71-4, about Nucleophilic catalysis of p-substituted aniline derivatives in acylhydrazone formation and exchange. Author is Canal-Martin, Andrea; Navo, Claudio D.; Saez, Elena; Molero, Dolores; Jimenez-Oses, Gonzalo; Perez-Fernandez, Ruth.

A mechanistic study and superior performance of electron-rich p-substituted aniline derivatives as catalysts for efficient hydrazone formation and exchange in both protic and aprotic solvents was reported. Rigorous kinetic analyses demonstrate that imine formation with 3-hydroxy-4-nitrobenzaldehyde and aniline derivatives proceeds with unprecedented third-order kinetics in which the aldehyde consistently shows a partial order of two. Computational investigations provide insights into the mechanisms of these transformations.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Computed Properties of C8H12O4. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: cis-Cyclohexane-1,2-dicarboxylic acid, is researched, Molecular C8H12O4, CAS is 610-09-3, about FT-IR and FT-Raman spectroscopy study of the cyclic anhydride intermediates for the esterification of cellulose. Part 3. Cyclic anhydrides formed by the isomers of cyclohexanedicarboxylic acid. Author is Yang, Charles Q.; Zhang, Guobao.

Multifunctional carboxylic acids were used as crosslinking agents for cotton and wood pulp cellulose. In the authors’ previous research, the authors found that a polycarboxylic acid esterifies cellulose through the formation of a 5-membered cyclic anhydride intermediate by the dehydration of 2 carboxyl groups. The authors studied the formation of those cyclic anhydride intermediates by different isomers of cyclohexanedicarboxylic acid (CHA) so that the authors can elucidate the effects of mol. structure on the formation of the anhydride intermediates. The authors found that both cis- and trans-1,2-CHA form 5-membered anhydride intermediates when temperature reaches their m.p. and that cis-1,2-CHA forms the cyclic anhydride at temperatures lower than does trans-1,2-CHA. 1,3-CHA forms 6-membered cyclic anhydride at temperatures much higher than its m.p. The formation of a 5-membered cyclic anhydride intermediates takes place at temperatures lower than that of a 6-membered anhydride. This is probably the main reason why those polycarboxylic acids with their carboxylic acid groups bonded to the adjacent carbons of the mol. backbones are more effective crosslinking agents for cellulose than those with their carboxylic groups bonded to the alternative carbons. No formation of cyclic anhydride was found for 1,4-CHA. The formation of a 5-membered cyclic anhydride was accelerated by monosodium phosphate, which is used as a catalyst for the esterification of cotton cellulose by polycarboxylic acids.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics