6619-58-5

Upstream product

• 996-82-7 sodium diethylmalonate 
• 104-82-5 4-Methylbenzyl chloride 
• 104-81-4 4-Methylbenzyl bromide 
• 105-53-3 diethyl malonate 
• 95-47-6 o-xylene 
• 104-87-0 4-methyl-benzaldehyde 
• 104-84-7 para-methylbenzylamine 
• 14111-33-2 diethyl 2-(4-methylbenzylidene)malonate 

Downstream Products

• 94853-59-5 ethyl 2-carbethoxy-2-(p-methylbenzyl)-4-formylbutanoate 
• 1049796-79-3 diethyl 2-(4-methylbenzyl)-2-(prop-2-ynyl)malonate 
• 14111-33-2 diethyl 2-(4-methylbenzylidene)malonate 
• 1608506-11-1 C₁₈H₂₃NO₄ 
• 1608506-57-5 C₁₃H₁₇N₃O₂ 
• 1608506-47-3 C₁₃H₁₆N₄ 
• 1608506-27-9 C₁₃H₁₇NO 
• 1608506-19-9 C₁₅H₁₉NO₂ 
• 1608506-67-7 C₁₃H₁₆ClN₃O 

Relevant academic research and scientific papers

Programmed Sequential Additions to Halogenated Mucononitriles

Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,1,3-benzothiadiazole and undergo conjugate addition/elimination reactions with both nitrogen (40-95% yield) and carbon nucleophiles (72-93% yield). Secondary amines undergo monosubstitutions, while carbon nucleophiles are added twice. The sequence of addition of the nucleophiles could be controlled to give mixed addition products. The multicomponent coupling products could then be converted to natural product like motifs using intramolecular cyclization reactions.

Environmentally benign nucleophilic substitution reaction of arylalkyl halides in water using CTAB as the inverse phase transfer catalyst

An environmentally benign, practically scalable and highly selective C-arylalkylation of active methylene compounds is developed using CTAB as the inverse phase transfer catalyst in water. The methodology developed is elaborated into the one-pot synthesis of quinoline derivatives and also applicable to the regioselective N-aralkyl of 2-pyridones.

Aryltrifluoromethylative cyclization of unactivated alkenes by the use of PhICF3Cl under catalyst-free conditions

A concise and catalyst-free aryltrifluoromethylative cyclization of unactivated alkenes has been developed herein. The use of PhICF3Cl as a powerful trifluoromethylating agent allows easy transformations. A set of trifluoroethylated carbocycles and aza-hereocycles were efficiently synthesized in good yield and selectivity. A broad substrate scope, mild reaction conditions, and easy operation would make this method well-suited for applications.

Synthesis and insecticidal activity of mesoionic pyrido[1,2-α]pyrimidinone derivatives containing a neonicotinoid moiety

Mesoionic pyrido[1,2-α]pyrimidinone derivatives containing a neonicotinoid moiety were designed, synthesized, and evaluated for their insecticidal activity. Some of the title compounds showed remarkable insecticidal properties against Aphis craccivora. Compound I13 exhibited satisfactory insecticidal activity against A. craccivora. Meanwhile, label-free proteomics analysis of compound I13 treatment identified a total of 821 proteins. Of these, 35 proteins were up-regulated, whereas 108 proteins were down-regulated. Differential expressions of these proteins reflected a change in cellular structure and metabolism.

Biocatalytic Desymmetrization of Prochiral 3-Aryl and 3-Arylmethyl Glutaramides: Different Remote Substituent Effect on Catalytic Efficiency and Enantioselectivity

Catalyzed by an amidase-containing Rhodococcus erythropolis AJ270 microbial whole cell catalyst in neutral phosphate buffer at 30 °C, desymmetric hydrolysis of a series of prochiral 3-aryl and 3-arylmethylglutaramides efficiently afforded 3-substituted glutaric acid monoamides in up to 95% yield and >99.5% ee. Even far away from the reaction site, the substituents on the aryl still have a significant effect on the catalytic activity and enantioselectivity and different remote substituent effect was observed for the two types of substrates. The synthetic application of biocatalytic desymmetrization was demonstrated by the facile transformation of the obtained enantiopure (R)-3-substituted 4-carbamoylbutanoic acid products to chiral dihydroquinolinone and δ-lactone compounds. (Figure presented.).

Highly efficient synthesis of functionalized dihydronaphthalenes, tetrahydronaphthalenes, and tetrahydroisoquinolines by iron-catalyzed intramolecular Friedel-Crafts reaction of aryl-containing propargylic alcohols

An efficient, convenient, and one-pot procedure for the synthesis of a series of new dihydro- and tetrahydronaphthalenes as well as tetrahydroisoquinolines has been established through Lewis acid-catalyzed intramolecular Friedel-Crafts reaction of aryl-substituted propargylic alcohols.

Controllable one-step synthesis of spirocycles, polycycles, and di- and tetrahydronaphthalenes from aryl-substituted propargylic alcohols

(Chemical Equation Presented) A novel, convenient, and efficient method has been developed for selective synthesis of spirocycle, polycycle, and di-and tetrahydronaphthalene systems from aryl-substituted propargylic alcohols by FeCl3- or TsOH-catalyzed multiple activations of unsaturated C-C bonds and C-H bonds.

A facile experimental method to determine the hydride affinity of polarized olefins in acetonitrile

(Chemical Equation Presented) Choosing a suitable hydride reducing agent and thermodynamic analysis of reduction mechanisms is facilitated by experimental hydride affinities ΔHH-A, which are reported herein for 28 polarized olefins 1 in acetonitrile (see scheme). The method should also be applicable to ketones, aldehydes, and imines.

Structure-activity relationships of dimethindene derivatives as new M2-selective muscarinic receptor antagonists

A series of 2,3-disubstituted indenes, which are analogues of the widely used histamine H1 receptor antagonist dimethindene, have been synthesized and studied as muscarinic and histamine receptor antagonists. The affinities of these compounds for the five human muscarinic receptor subtypes (M1-M5) and for human histamine H1 receptors were determined in radioligand binding studies using membranes from transfected Chinese hamster ovary (CHO) cells and [3H]N-methylscopolamine ([3H]NMS). The results demonstrate that the diisopropyl analogue 19 has a similar high affinity as (S)-dimethindene at M2 receptors ((S)-dimethindene: pKi = 7.52; (-)-19: pKi = 7.37) with an improved selectivity pattern ((S)-dimethindene: M2/M1 = 6-fold, M2/M3 = 5-fold, M2/M4 = 10-fold, M2/M5 = 25-fold; (-)-19: M2/M1 = 36-fold, M2/M3 = 96-fold, M2/M4 = 42-fold, M2/M5 = 275-fold). In addition, compound (-)-19 showed 35-fold lower affinity at histamine H1 receptors (pKi = 5.61) than (S)-dimethindene (pKi = 7.16). Another interesting compound is the fluoroethyl derivative 20 (pKi/M2 = 7.49), which also exhibits a higher M2 selectivity (M2/M1 = 19-fold; M2/M3 = 22-fold; M2/M4 13-fold; M2/M5 = 62-fold) than (S)-dimethindene. Unfortunately, compound 20 also shows a high affinity for histamine H1 receptors (pKi = 8.14). The compound with the highest affinity for M2 receptors (pKi = 7.91), the dimethylaminomethylene analogue 31, displayed only a small preference for M2 receptors. In conclusion, compound (-)-19 might be useful to test the hypothesis that blockade of muscarinic M2 receptors in the brain is a viable mechanism by which to produce improved cognition. This second-generation dimethindene analogue might also be the starting point for the development of M2-selective muscarinic antagonists useful for quantifying M2 receptors in the central nervous system with positron emission tomography imaging.

The effect of vinyl esters on the enantioselectivity of the lipase-catalysed transesterification of alcohols

The enantioselectivity of the lipase from Pseudomonas cepacia (PCL) in the transesterification of 2-phenyl-1-propanol 1 was studied using a series of vinyl 3-arylpropanoates as acyl donors. The most enantioselective transesterification reaction of the alcohol was attained by using vinyl 3-(p-iodophenyl)- or 3-(p-trifluoromethylphenyl)propanoates, with enantiomer ratios, E, of 116 and 138, respectively. Vinyl 3-phenylpropanoate was also effective for the resolution of 1 mediated by lipases from P. fluorescens and porcine pancreas and for the PCL-catalysed transesterification of several 2-phenyl-1-alkanols. The enantiomeric resolution of 1 was practically carried out by the first enantioselective transesterification using PCL and vinyl 3-(p-iodophenyl)propanoate to afford (R)-1 and then the enantioselective hydrolysis of the resultant ester to afford (S)-1.