51220-06-5

Upstream product

• 141-97-9 ethyl acetoacetate 
• 105-07-7 4-cyanobenzaldehyde 
• 67-64-1 acetone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 

Downstream Products

• 82323-88-4 α-(4-cyanophenyl)-4-oxopentanenitrile 
• 1115878-79-9 C₁₅H₁₉NOS 
• 1195190-89-6 4-((3aR,4R,7aS)-2-benzyl-1,3,6-trioxooctahydro-1H-isoindol-4-yl)benzonitrile 
• 1195191-03-7 4-((3aS,4S,7aR)-2-benzyl-1,3,6-trioxooctahydro-1H-isoindol-4-yl)benzonitrile 
• 1195190-78-3 ethyl (1S,2S,6S)-1-cyano-2-(4-cyanophenyl)-4-oxo-6-phenylcyclohexanecarboxylate 
• 1194653-82-1 4-((1S,2S,6S)-2',4-dioxo-2-phenylspiro[cyclohexane-1,3'-indoline]-6-yl)benzonitrile 
• 1338577-23-3 3-O-[(E)-4-(4-cyanophenyl)-2-oxobut-3-en-1-yl]kaempferol 
• 558644-29-4 4-(5-methyl-1H-pyrazol-3-yl)benzonitrile 

Relevant academic research and scientific papers

Organocatalytic diastereo- And enantioselective oxa-hetero-Diels-Alder reactions of enones with aryl trifluoromethyl ketones for the synthesis of trifluoromethyl-substituted tetrahydropyrans

Tetrahydropyran derivatives are found in bioactives, and introduction of the trifluoromethyl group into molecules often improves biofunctions. Here we report diastereo- and enantioselective oxa-hetero-Diels-Alder reactions catalyzed by amine-based catalyst systems that afford trifluoromethyl-substituted tetrahydropyranones. Catalyst systems and conditions suitable for the reactions to provide the desired diastereomer products with high enantioselectivities were identified, and various trifluoromethyl-substituted tetrahydropyranones were synthesized with high diastereo- and enantioselectivities. Mechanistic investigation suggested that the reactions involve a [4 + 2] cycloaddition pathway, in which the enamine of the enone acts as the diene and the ketone carbonyl group of the aryl trifluoromethyl ketone acts as the dienophile. In this study, tetrahydropyran derivatives with the desired stereochemistry that are difficult to synthesize by previously reported methods were concisely obtained, and the range of tetrahydropyran derivatives that can be synthesized was expanded. This journal is

1,3-disubstituted pyrazole derivative as well as preparation method and application thereof

The invention discloses a 1,3-disubstituted pyrazole derivative as well as a preparation method and application thereof. The compound has a structure shown as a general formula (I). The invention further provides a preparation method of the compounds and

Application of Deep Eutectic Solvents in Promiscuous Lipase-Catalysed Aldol Reactions

The application of deep eutectic solvents has been demonstrated for the first time in promiscuous lipase-catalysed aldol reactions. The model reaction between 4-nitrobenzaldehyde and acetone was examined in depth, with excellent compatibility being found between porcine pancreas lipase and choline chloride/glycerol mixtures for the formation of the aldol product in high yields. The system was compatible with a series of aromatic aldehydes and ketones including acetone, cyclopentanone and cyclohexanone. In some cases, the corresponding α,β-unsaturated carbonyl compounds were found as minor products. Control experiments demonstrate that the enzymatic preparation was also responsible for a collateral dehydration reaction once the aldol product is formed. Deep eutectic solvents are used for the first time in promiscuous lipase-catalysed aldol reactions. The reaction between substituted benzaldehydes and aliphatic ketones has excellent compatibility with porcine pancreas lipase (PPL) and choline chloride/glycerol mixtures and gives the aldol product in high yields. PPL was also responsible for a collateral dehydration reaction.

Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy

An efficient strategy for the one-pot synthesis of polysubstituted pyridines via a cascade reaction from aldehydes, phosphorus ylides, and propargyl azide is reported. The reaction sequence involves a Wittig reaction, a Staudinger reaction, an aza-Wittig reaction, a 6π-3-azatriene electrocyclization, and a 1,3-H shift. This protocol provides quick access to the polysubstituted pyridines from readily available substrates in good to excellent yields.

Carbon quantum dots with photoenhanced hydrogen-bond catalytic activity in aldol condensations

Carbon quantum dots (CQDs) were synthesized by an electrochemical etching method. The CQDs are well-dispersed with uniform size about 5 nm. FT-IR spectra suggest the presence of many hydroxyl groups on the surface of CQDs. Here, CQDs with diameter approximately 5 nm, directly used as effective heterogeneous nanocatalysts for H-bond catalysis in aldol condensations, show excellent photoenhanced catalytic ability (89% yields when 4-cyanobenzaldehyde is used). It demonstrated that aldol condensation between acetone and aromatic aldehydes resulted in higher yields with visible light irradiation than in the dark, confirming visible light is necessary for good conversion. The H-bond catalytic activities of CQDs can be significantly enhanced with visible light irradiation. The high catalytic activities of CQDs are due to highly efficient electron-accepting capabilities. Repeated catalytic experiments suggest that the CQD catalyst can be easily recycled as a heterogeneous catalyst with a long catalyst life.

FLAVONE DERIVATIVES AND THEIR PREPARATIVE METHOD AND MEDICAL USE

Flavone derivatives, preparative method of the derivatives and use thereof as medicaments for treating diabetes. The structure of the derivatives is presented by formula 1: In the structure, R1 and R2, which are identical or not, represent hydrogen atom, halogen, cyano, hydroxyl, trifluoromethyl, thio-methyl, benzyloxy, C1-C8 linear chain or branch chain alkyl, C1-C8 linear chain or branch chain alkoxy. The pharmacological test indicates that the flavone derivatives can significantly increase the glucose consumption of Hep-G2 cell with insulin resistance activity, promote translocation of glucose transporter 4 of skeletal muscle cells (L6GLUT4myc) at different level, and significantly increase glucose intake and utilization by cells. The test proves the fact for the first time that the flavone derivatives can significantly promote translocation of glucose transporter 4 of skeletal muscle cells, and one of the mechanisms for treating diabetes is activating the cell AMPK phosphorylation and phosphorylating the downstream ACC.

Novel diarylheptanoids as inhibitors of TNF-α production

Synthesis and anti-inflammatory activity of novel diarylheptanoids [5-hydroxy-1-phenyl-7-(pyridin-3-yl)-heptan-3-ones and 1-phenyl-7-(pyridin-3-yl) hept-4-en-3-ones] as inhibitors of tumor necrosis factor-α (TNF-α) production is described in the present article. The key reactions involve the formation of a β-hydroxyketone by the reaction of substituted 4-phenyl butan-2-ones with pyridine-3-carboxaldehyde in presence of LDA and the subsequent dehydration of the same to obtain the α,β-unsaturated ketones. Compounds 4i, 5b, 5d, and 5g significantly inhibit lipopolysaccharide (LPS)-induced TNF-α production from human peripheral blood mononuclear cells in a dose-dependent manner. Of note, the in vitro TNF-α inhibition potential of 5b and 5d is comparable to that of curcumin (a naturally occurring diarylheptanoid). Most importantly, oral administration of 4i, 5b, 5d, and 5g (each at 100 mg/kg) but not curcumin (at 100 mg/kg) significantly inhibits LPS-induced TNF-α production in BALB/c mice. Collectively, our findings indicate that these compounds may have potential therapeutic implications for TNF-α-mediated auto-immune/inflammatory disorders.

Synthesis and biological activity of novel tiliroside derivants

A series of new tiliroside derivatives were synthesized and characterized by analytical 1H NMR, 13C NMR and mass spectrometry. All of the compounds were evaluated for anti-diabetic properties in vitro using HepG2 cells. Compounds 3c, 3d, and 3i-l caused significant enhancements in glucose consumption by insulin-resistant HepG2 cells compared with control cells and cells that were exposed to metformin (an anti-diabetic drug). Moreover, compound 3l significantly activated adenosine 5′-monophosphate-activated protein kinase activity and reduced acetyl-CoA carboxylase activity. Thus, the tiliroside derivative 3l offers potential to be developed as a new approach for treating type II diabetes.

A simple and efficient synthesis of pyrazoles in water

A simple, highly efficient, and environmentally friendly method for the synthesis of substituted 1H-pyrazoles by one-pot condensation reaction of α,β-unsaturated carbonyl compounds with tosyl hydrazide in water was developed. The reaction system exhibited tolerance with various functional groups, Aromatic moiety with both electron-rich and electron-deficient substituents could give desired products in good to excellent yields.

Synthesis of acid-base bifunctional mesoporous materials by oxidation and thermolysis

A novel and efficient method has been developed for the synthesis of acid-base bifunctional catalyst SO3H-MCM-41-NH2. This method was achieved by co-condensation of tetraethylorthosilicate (TEOS), 3-mercaptopropyltrimethoxysilane (MPTMS) and (3-triethoxysilylpropyl) carbamicacid-1-methylcyclohexylester (3TAME) in the presence of cetyltrimethylammonium bromide (CTAB), followed by oxidation and then thermolysis to generate acidic site and basic site. X-ray diffraction (XRD) and transmission electron micrographs (TEM) show that the resultant materials keep mesoporous structure. Thermogravimetric analysis (TGA), X-ray photoelectron spectra (XPS), back titration, solid-state 13C CP/MAS NMR and solid-state 29Si MAS NMR confirm that the organosiloxanes were condensed as a part of the silica framework. The bifunctional sample (SO 3H-MCM-41-NH2) containing amine and sulfonic acids exhibits excellent acid-basic properties, which make it possess high activity in aldol condensation reaction between acetone and various aldehydes.