102-25-0Relevant academic research and scientific papers
Preparation of 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene from two versatile 1,3,5-tri(halosubstituted) 2,4,6-triethylbenzene derivatives
Wallace, Karl J.,Hanes, Robert,Anslyn, Eric,Morey, Jeroni,Kilway, Kathleen V.,Siegel, Jay
, p. 2080 - 2083 (2005)
The use of 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene and the intermediates 1,3,5-tris(halomethyl)-2,4,6-triethylbenzene (halo = bromo and chloro) compounds, have been utilized as scaffolds for many molecular receptors. We report here for the first time a detailed practical synthetic procedure, starting from benzene, and in four straightforward steps, to prepare 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene, a very versatile molecular scaffold. The added advantage is the limited chromatography in the purification procedure. Georg Thieme Verlag Stuttgart.
Supramolecular Alloys from Fluorinated Hybrid Tri4Di6 Imine Cages
Kunde, Tom,Pausch, Tobias,Schmidt, Bernd M.
, p. 8457 - 8460 (2021)
To create innovative materials, efficient control and engineering of pore sizes and their characteristics, crystallinity and stability is required. Eight hybrid Tri4Di6 imine cages with a tunable degree of fluorination and one fully fluorinated Tri4Di6 imine cage are investigated. Although the fluorinated and the non-fluorinated building blocks used herein differ vastly in reactivity, it was possible to gain control over the outcome of the self-assembly process, by carefully controlling the feed ratio. This represents the first hybrid material based on fluorinated/hydrogenated porous organic cages (POCs). These cages with unlimited miscibility in the solid state were obtained as highly crystalline samples after recrystallization and even showed retention of the crystal lattice, forming alloys. All mixtures and the fully fluorinated Tri4Di6 imine cage were analyzed by MALDI-MS, single-crystal XRD, powder XRD and in regard to thermal stability (TGA).
Regioselective synthesis of 1,3,5-substituted benzenes via the InCl 3/2-iodophenol-catalyzed cyclotrimerization of alkynes
Xu, Yan-Li,Pan, Ying-Ming,Wu, Qiang,Wang, Heng-Shan,Liu, Pei-Zhen
, p. 8472 - 8476 (2011)
A novel indium(III)-catalyzed cyclotrimerization of alkynes in the presence of 2-iodophenol gave 1,3,5-substituted benzenes in excellent yields with complete regioselectivity. The reaction condition is tolerant to air, and atom economical, in accordance with the concept of modern green chemistry. This method provides a rapid and efficient access to 1,3,5-substituted benzenes.
Guaiacol demethoxylation catalyzed by Re2O7 in ethanol
Yan, Fei,Sang, Yushuai,Bai, Yunfei,Wu, Kai,Cui, Kai,Wen, Zhe,Mai, Fuhang,Ma, Zewei,Yu, Linhao,Chen, Hong,Li, Yongdan
, p. 231 - 237 (2019/08/12)
Re2O7 is used to convert guaiacol in alcohols at 280–320 °C. In ethanol, guaiacol is deoxygenated and alkylated, and the major products are phenol and alkylphenols (including ethylphenol, diethylphenol, diisopropylphenol, di-tert-butylphenol and 2,6-di-tert-butyl-4-ethylphenol), accounting for 97 mol% of all products after 6 hour reaction at 320 °C. Both catechol and phenol are the intermediates of guaiacol demethoxylation. Among the substituents, ethyl is directly provided by ethanol while isopropyl and tert-butyl are formed by the addition of methyl to ethyl step by step. In addition, Re2O7 has negligible activity for the saturation of benzene ring so it does not cause considerable over-consumption of reductant. The actual catalyst for guaiacol demethoxylation is likely a ReIV?VI species.
Unraveling the Homologation Reaction Sequence of the Zeolite-Catalyzed Ethanol-to-Hydrocarbons Process
Chowdhury, Abhishek Dutta,Lucini Paioni, Alessandra,Whiting, Gareth T.,Fu, Donglong,Baldus, Marc,Weckhuysen, Bert M.
supporting information, p. 3908 - 3912 (2019/02/20)
Although industrialized, the mechanism for catalytic upgrading of bioethanol over solid-acid catalysts (that is, the ethanol-to-hydrocarbons (ETH) reaction) has not yet been fully resolved. Moreover, mechanistic understanding of the ETH reaction relies heavily on its well-known “sister-reaction” the methanol-to-hydrocarbons (MTH) process. However, the MTH process possesses a C1-entity reactant and cannot, therefore, shed any light on the homologation reaction sequence. The reaction and deactivation mechanism of the zeolite H-ZSM-5-catalyzed ETH process was elucidated using a combination of complementary solid-state NMR and operando UV/Vis diffuse reflectance spectroscopy, coupled with on-line mass spectrometry. This approach establishes the existence of a homologation reaction sequence through analysis of the pattern of the identified reactive and deactivated species. Furthermore, and in contrast to the MTH process, the deficiency of any olefinic-hydrocarbon pool species (that is, the olefin cycle) during the ETH process is also noted.
Synthesis, characterization and application of MCM-22 zeolites via a conventional HMI route and temperature-controlled phase transfer hydrothermal synthesis
Xing, Enhui,Shi, Yanchun,Xie, Wenhua,Zhang, Fengmei,Mu, Xuhong,Shu, Xingtian
, p. 8514 - 8522 (2015/03/05)
With less environmental and economical impact, temperature-controlled phase transfer hydrothermal synthesis of MWW zeolites was realized with hexamethyleneimine as a structure-directing agent and aniline as a structure-promoting agent. MCM-22 zeolite, synthesized via temperature-controlled phase transfer hydrothermal synthesis, is nearly identical concerning chemical composition and structure, and possesses nearly identical properties with respect to porosity, Si/Al ratio, thermal behavior and catalytic activity at 200°C, compared with that made from conventional synthesis with hexamethyleneimine as the only template.
Silica-supported tripod triarylphosphines: Application to palladium-catalyzed borylation of chloroarenes
Iwai, Tomohiro,Harada, Tomoya,Tanaka, Ryotaro,Sawamura, Masaya
supporting information, p. 584 - 586 (2014/05/20)
Silica-supported tripod triarylphosphines that have a Ph3Ptype core tripodally immobilized on a silica surface enabled the Pd-catalyzed borylation of chloroarenes with bis(pinacolato)diboron under mild conditions. The immobilization in tripod was crucial for the excellent performance of the Ph3P-based ligands.
An efficient approach to the cyclotrimerisation of alkynes: Solvent-free synthesis of 1,3,5-trisubstituted benzenes using p-toluenesulfonic acid monohydrate
Gao, Qi,Bao, Fang-Ping,Feng, Xiao-Jing,Pan, Ying-Ming,Wang, Heng-Shan,Li, Dian-Peng
, p. 49 - 60 (2013/04/24)
An environmentally friendly, efficient method for transforming alkynes into substituted benzenes catalyzed by p-toluenesulfonic acid monohydrate (p-TsOH·H2O) under solvent-free conditions has been developed, which conforms to the principles of "green" chemistry and overcomes the shortcomings of previous methods for the synthesis of substituted benzenes. The reaction is quite general and provides good to excellent yields. ARKAT-USA, Inc.
Isopropylamino and isobutylamino groups as recognition sites for carbohydrates: Acyclic receptors with enhanced binding affinity toward β-galactosides
Mazik, Monika,Sonnenberg, Claudia
scheme or table, p. 6416 - 6423 (2010/12/20)
Binding motifs observed in the crystal structures of protein-carbohydrate complexes, in particular the participation of the isopropyl/isobutyl side chain of valine/leucine in the formation of van der Waals contacts, have inspired the design of new artificial carbohydrate receptors. The new compounds, containing a trisubstituted triethylbenzene core, were expected to recognize sugar molecules through a combination of NH→O and OH→N hydrogen bonds, CH→π interactions, and numerous van der Waals contacts. 1H NMR spectroscopic titrations in competitive and noncompetitive media, as well as binding studies in two-phase systems, such as dissolution of solid carbohydrates in apolar media and phase transfer of sugars from aqueous into organic solvents, revealed effective recognition of neutral carbohydrates and β- vs α-anomer binding preferences in the recognition o' glycosides as well as significantly increased binding affinity of the receptors toward β-galactoside in comparison with the previously described receptors.
Molybdenum(III) chloride-tetrahydrothiophene (tht) complexes in the catalytic polymerization and cyclotrimerization of alkynes: Structures and reactivities of the possible intermediates [MoCl3(tht)2(PhC≡CR)] (R = Me or Et)
Boorman, P. Michael,Wang, Meiping,Parvez, Masood
, p. 4533 - 4542 (2007/10/03)
The binuclear complexes [Mo2Cl6(tht)3] (both the C2r and Cs isomers, tht = tetrahydrothiophene) have been found to be active catalysts for the selective polymerization and cyclotrimerization of a variety of alkynes. The mononuclear complex [MoCl3(tht)3] shows similar behaviour, leading to the postulate that the active species in all cases is mononuclear. Two unique molybdenum(III) alkyne complexes, [MoCl3(tht)2L] (L = PhC≡CMe or PhC≡CEt) have been isolated and structurally characterized. The structural parameters for these complexes suggest that the alkynes behave as four-electron donors. These complexes are also catalytically active, and the alkyne L is incorporated into the product cyclotrimers and polymers suggesting they are the first intermediates in the formation of active catalysts from the original thioether complexes.
