454203-57-7

Upstream product

• 108-91-8 cyclohexylamine 
• 23165-29-9 3,5-bistrifluoromethylphenylisothiocyanate 

Downstream Products

• 1404310-25-3 C₁₅H₁₆F₆N₂S*C₅H₈O₂ 

Relevant academic research and scientific papers

γ-Butyrolactone Copolymerization with the Well-Documented Polymer Drug Carrier Poly(ethylene oxide)-block-poly(ε-caprolactone) to Fine-Tune Its Biorelevant Properties

Polymeric drug carriers exhibit excellent properties that advance drug delivery systems. In particular, carriers based on poly(ethylene oxide)-block-poly(ε-caprolactone) are very useful in pharmacokinetics. In addition to their proven biocompatibility, there are several requirements for the efficacy of the polymeric drug carriers after internalization, e.g., nanoparticle behavior, cellular uptake, the rate of degradation, and cellular localization. The introduction of γ-butyrolactone units into the hydrophobic block enables the tuning of the abovementioned properties over a wide range. In this study, a relatively high content of γ-butyrolactone units with a reasonable yield of ≈60% is achieved by anionic ring-opening copolymerization using 1,5,7-triazabicyclo[4.4.0]dec-5-ene as a very efficient catalyst in the nonpolar environment of toluene with an incorporated γ-butyrolactone content of ≈30%. The content of γ-butyrolactone units can be easily modulated according to the feed ratio of the monomers. This method enables control over the rate of degradation so that when the content of γ-butyrolactone increases, the rate of degradation increases. These findings broaden the application possibilities of polyester-polyether-based nanoparticles for biomedical applications, such as drug delivery systems.

Hydrogen-bonding catalysts based on fluorinated alcohol derivatives for living polymerization

Recognize this! A hydrogen-bonding motif based on hexafluorinated alcohol derivatives (see picture; O red, F yellow) activates electrophilic substrates. The catalytic activity of the hydrogen-bonded systems was demonstrated for the ring-opening polymeriza

Squaramide–Quaternary Ammonium Salt as an Effective Binary Organocatalytic System for Oxazolidinone Synthesis from Isocyanates and Epoxides

Squaramide–quaternary ammonium salt is illustrated as a simple, tunable, and competent metal-free binary catalytic platform for the atom-economic conversion of epoxides and isocyanates into oxazolidinones. Although, various metal catalysts have been employed for the title reaction, application of organocatalysis is scarce. At first, a rational survey of catalytic activity of several air-stable and architecturally distinct squaramides was undertaken. Thereafter, the impact on catalytic capability of different parameters, such as temperature, catalyst loading, and nature of nucleophiles, was examined. This binary organocatalytic system for the oxazolidinone synthesis, composed of a squaramide entity along with a suitable halide anion, was applied to the challenging conversion of a plethora of alkyl- and aryl-substituted epoxides– including disubstituted and enantioenriched ones– and isocyanates into the corresponding oxazolidinones in high-to-excellent yields. The time-dependent formation of oxazolidinone from epoxide and isocyanate was monitored by FTIR-ATR and 1H NMR spectroscopy and the scalability of this process was also described. In light of 1H NMR experiment, a hydrogen-bonding/anion-binding mechanism was proposed wherein the nucleophilic ring-opening operation, and oxo- and carbamate-anions stabilization occur cooperatively towards isocyanate fixation.

Synergetic Organocatalysis for Eliminating Epimerization in Ring-Opening Polymerizations Enables Synthesis of Stereoregular Isotactic Polyester

Ring-opening polymerization of O-carboxyanhydrides (OCAs) can furnish polyesters with a diversity of functional groups that are traditionally hard to harvest by polymerization of lactones. Typical ring-opening catalysts are subject to unavoidable racemization of most OCA monomers, which hampers the synthesis of highly isotactic crystalline polymers. Here, we describe an effective bifunctional single-molecule organocatalysis for selective ring-opening polymerization of OCAs without epimerization. The close vicinity of both activating groups in the same molecule engenders an amplified synergetic effect and thus allows for the use of mild bases, thereby leading to minimal epimerization for polymerization. Ring-opening polymerization of manOCA monomer (OCA from mandelic acid) mediated by the bifunctional single-molecule organocatalyst yields highly isotactic poly(mandelic acid) (PMA) with controlled molecular weights (up to 19.8 kg mol-1). Mixing of the two enantiomers of PMA generates the first example of a crystalline stereocomplex in this area, which displayed distinct Tm values around 150 °C. Remarkably, the bifunctional catalysts are moisture-stable, recyclable, and easy to use, allowing sustainable and scalable synthesis of a stereoregular functional polyester.

METHOD FOR PRODUCING 5-HYDROXYMETHYLFURFURAL IN THE PRESENCE OF A LEWIS ACID CATALYST AND/OR A HETEROGENEOUS BASE CATALYST AND A HOMOGENEOUS ORGANIC BR?NSTED ACID CATALYST IN THE PRESENCE OF AT LEAST ONE APROTIC POLAR SOLVENT

The invention relates to a process for the production of 5-hydroxymethylfurfural from a feedstock comprising at least one sugar using a combination of at least one catalyst selected from the homogeneous Lewis acids, the heterogeneous Lewis acids and the h

PROCESS FOR THE PRODUCTION OF 5-HYDROXYMETHYLFURFURAL IN THE PRESENCE OF ORGANIC CATALYSTS FROM THE THIOUREA FAMILY

A process for the transformation of a feed of at least one sugar into 5-hydroxymethylfurfural, contacting the feed with one or more organic catalysts in the presence of at least one solvent, said solvent being water or an organic solvent, alone or as a mi

Synthesis, antibacterial and anti-MRSA activity, in vivo toxicity and a structure-activity relationship study of a quinoline thiourea

We report the synthesis, antibacterial evaluation of a series of thiourea-containing compounds. 1-(3,5-Bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)-((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea 5, was the most active against a rang

ANTIBACTERIAL AND/OR ANTIFOULING POLYMERS

The present disclosure provides a copolymer comprising monomer units represented by formulas (I) and/or (II) as disclosed and defined herein which are useful in antibacterial and/or antifouling coatings. The present disclosure further provides methods of

Application of "hydrogen bonding interaction" in new drug development: Design, synthesis, antiviral activity, and sars of thiourea derivatives

A series of simple thiourea derivatives were designed based on the structure of natural product harmine and lead compound and synthesized from amines in one step. The antiviral activity of these thiourea derivatives was evaluated. Most of them exhibited significantly higher anti-TMV activity than commercial plant virucides ribavirin, harmine, and lead compound. The hydrogen bond was found to be important but not the more the better. The optimal compound (R,R)-20 showed the best anti-TMV activity in vitro and in vivo (in vitro activity, 75%/500 a??g/mL and 39%/100 a??g/mL; inactivation activity, 71%/500 a??g/mL and 35%/100 a??g/mL; curative activity, 73%/500 a??g/mL and 37%/100 a??g/mL; protection activity, 69%/500 a??g/mL and 33%/100 a??g/mL), which is significantly higher than that of Ningnanmycin. The systematic study provides strong evidence that these simple thiourea derivatives could become potential TMV inhibitors.

Rational investigations in the ring opening of cyclic carbonates by amines

Non-isocyanate polyurethanes (NIPUs) constitute a promising alternative for more classical polyurethanes (PUs) as they may display mechanical properties that can match those of PUs and their synthesis does not involve the use of toxic isocyanates. Yet, because of the lower reactivity of carbonates versus isocyanates, the synthesis of NIPUs is not straightforward and generally requires the use of a catalyst. Recently, several groups have reported on the use of different ranges of catalysts for promoting the nucleophilic attack of the amine on the carbonate. However, many of these studies involve the use of highly reactive amine and/or carbonate proscribing a complete panorama of the potentialities of the reaction. Herein, we propose a rational study of the catalyzed aminolysis of four representative cyclic carbonates that reveals that the thiourea organocatalyst 1 outperforms in many aspects, classical inorganic or other organic catalysts. the Partner Organisations 2014.