94112-78-4

Upstream product

• 2947-60-6 3-methylbenzyl cyanide 
• 5256-74-6 1,3-diethyl 2-diazopropanedioate 
• 108-88-3 toluene 
• 621-36-3 m-methylphenylacetic acid 
• 40061-55-0 ethyl m-methylphenylacetate 
• 105-58-8 Diethyl carbonate 
• 105-53-3 diethyl malonate 
• 591-17-3 meta-bromotoluene 
• 625-95-6 3-Iodotoluene 
• 620-19-9 1-chloromethyl-3-methyl-benzene 
• 108-41-8 1-chloro-3-methylbenzene 
• 95-92-1 oxalic acid diethyl ester 

Downstream Products

• 53519-82-7 2-amino-2-(3-methylphenyl)acetic acid 
• 1196521-09-1 6-(2-(thiophen-2-yl)propan-2-yl)-3-m-tolylpyridine-2,4-diol 

Relevant academic research and scientific papers

Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chairlike six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed "methyl blocker"on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodology affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

Preparation method and application of 2-aryl malonic acid derivative

The invention provides a preparation method and application of 2-aryl malonic acid derivative. The preparation method includes: using a cyclohexenone derivative as a raw material to be in condensationreaction with a malonic acid derivative at the presence of a catalyst A to obtain a 2-(cyclohexenylene) malonic acid derivative; enabling the 2-(cyclohexenylene) malonic acid derivative to be in aromatization reaction under action of a catalyst B to obtain the 2-aryl malonic acid derivative. Compared with the prior art, the preparation method is totally different from existing methods in synthesis strategy and used raw materials and has the advantages that reaction raw materials are easy to obtain; no solvent is needed during reaction, and yield is high; the catalyst B can be recycled, so that cost is lowered; the preparation method is high in yield, few in three wastes, environment-friendly and conducive to industrial production.

Mesoionic Compound

The purpose of the present invention is to provide a mesoionic compound or a salt thereof that exhibits excellent control activity against various pests. Provided is a mesoionic compound represented by formula (1). (In the formula, Ra represents a hydrogen atom or a methyl group, R1 represents a phenyl group or pyridyl group which is optionally substituted with up to two substituents selected independently from R2, and R2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a c-propyl group, an n-butyl group, an i-butyl group, an s-butyl group, a t-butyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a methyloxy group, an ethyloxy group, an n-propyloxy group, an i-propyloxy group, a c-propyloxy group, an n-butyloxy group, an i-butyloxy group, a s-butyloxy group, a t-butyloxy group, an n-pentyloxy group, a trifluoromethyloxy group, a 2,2,2-trifluoroethyloxy group, a methylthio group, a methylsulfoxy group, a methylsulfonyl group, a vinyl group, an ethynyl group, etc.)

Protonation and transformations of α-diazo-β-dicarbonyl compounds in superacids: generation of the strongest carbon-centered cationic electrophiles at the protonation of diazomalonates in Friedel–Crafts reactions

Protonation of diazodiketones N2C(COR)2in Br?nsted superacids (TfOH, FSO3H, TfOH–SbF5) gives rise to stable and non-reactive O,O-diprotonated at carbonyl oxygens species N2C(C(=OH+)R)2, which were studied by means of1H and13C NMR. Diazomalonates N2C(CO2Alk)2, contrary to diazodiketones, react with TfOH or HF, releasing nitrogen and producing triflates of oxymalonates TfOCH(CO2Alk)2or fluoromalonates FCH(CO2Alk)2, respectively. Diazoketoesters N2C(COR)(CO2Alk) react in the same way only with TfOH, but not with HF. The reactions of diazomalonates with arenes ArH (benzene, toluene, xylenes) in TfOH solution yield corresponding Friedel–Crafts reaction products ArCH(CO2Alk)2. According to performed DFT calculations, trication+CH(C(=OH+)OMe)2, a possible intermediate, which is derived from protonation of dimethyl diazomalonate, should be the strongest cationic carbon-centered electrophile known up to date.

New efficient ligand-free, copper nanoparticle catalyzed coupling reactions of aryl halides with diethyl malonate to produce α-arylation of malonates

Recently synthesized copper nanoparticles (Cu NP) were used to catalyze coupling of aryl halides with diethyl malonates to produce α-aryl malonates. Synthetic conditions, including solvents, relative amounts of reactants, catalyst, and temperature, etc. h

Copper(I)-catalyzed C-C and C-O coupling reactions using hydrazone ligands

Copper-catalyzed C-C coupling reaction of aryl iodides with diethylmalonate in toluene at 90C gave arylated malonates using 5 mol% of CuI with hydrazone 1a as a ligand in good yields under an aerobic atmosphere. We also found CuI/hydrazone 1b in toluene to be an efficient catalytic system for C-O coupling reactions of aryl bromides with phenols to give aryl ethers in good yields at 110C under an aerobic atmosphere.

Pyrimidine Non-Classical Cannabinoid Compounds and Related Methods of Use

Disclosed are compounds of the formula I: wherein R1, R2, V, W, X, Y and Z can be as defined herein. The compounds can be used in the treatment of disorders mediated by the cannabinoid receptors.

Pyridine Non-Classical Cannabinoid Compounds and Related Methods of Use

wherein R1, R2, V, W, X, Y and Z can be as defined herein. The compounds can be used in the treatment of disorders mediated by the cannabinoid receptors.

ARYLATION OF DIETHYL MALONATE VIA NUCLEOPHILIC SUBSTITUTION REACTIONS WITH CYCLOPENTADIENYLIRON COMPLEXES OF CHLOROARENES

Reaction of an η6-chloroarene-η5-cyclopentadienyliron hexafluorophosphate with diethyl malonate in the presence of K2CO3 in THF/DMSO gave a corresponding SNAr product, η6-diethyl arylmalonate-η5-cyclopentadienyliron hexafluorophosphate, which, upon pyrolic sublimation, resulted in the liberation of the arylated malonic ester.Such esters prepared in the present work included RPhCH(COOEt)2, with R = o-, m- or p-CH3, 2,6-(CH3)2, or o-, m- or p-Cl.