138647-53-7

Basic information

• Product Name: 1(2H)-Pyridinecarboxylic acid, 3,6-dihydro-4-(4-methylphenyl)-, 1,1-dimethylethyl ester
• CAS NO: 138647-53-7
• Molecular Formula: C17H23NO2
• Molecular Weight: 273.375
• Mol File: 138647-53-7.mol

Chemical Properties

• CAS DataBase Reference: 1(2H)-Pyridinecarboxylic acid, 3,6-dihydro-4-(4-methylphenyl)-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1(2H)-Pyridinecarboxylic acid, 3,6-dihydro-4-(4-methylphenyl)-, 1,1-dimethylethyl ester(138647-53-7)
• EPA Substance Registry System: 1(2H)-Pyridinecarboxylic acid, 3,6-dihydro-4-(4-methylphenyl)-, 1,1-dimethylethyl ester(138647-53-7)

Safety Data

• Hazardous Substances Data: 138647-53-7(Hazardous Substances Data)

Upstream product

• 106-38-7 para-bromotoluene 
• 108-88-3 toluene 
• 375853-82-0 tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate 
• 138647-49-1 4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 162046-38-0 1-tert-butyloxycarbonyl-4-trimethylstannyl-1,2,5,6-tetrahydropyridine 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 59084-09-2 4-(4-methylphenyl)-1,2,3,6-tetrahydropyridine 

Relevant articles and documents

20-HETE FORMATION INHIBITORS

This disclosure provides novel heterocyclic compounds and methods for inhibiting the enzyme CYP4. Further disclosed methods include: a method of inhibiting the biosynthesis of 20-hydroxyeicosatetraenoic acid (20-HETE) in a subject in need thereof and a method of producing neuroprotection and decreased brain damage by preventing cerebral microvascular blood flow impairment and anti-oxidant mechanisms in a subject experiencing or having experienced an ischemic event.

para-Selective arylation and alkenylation of monosubstituted arenes using thianthreneS-oxide as a transient mediator

Using thianthreneS-oxide (TTSO) as a transient mediator,para-arylation and alkenylation of mono-substituted arenes have been demonstratedviaapara-selective thianthrenation/Pd-catalyzed thio-Suzuki-Miyaura coupling sequence under mild conditions. This reaction features a broad substrate scope, and functional group and heterocycle tolerance. The versatility of this approach was further demonstrated by late-stage functionalization of complex bioactive scaffolds, and direct synthesis of some pharmaceuticals, including Tetriprofen, Ibuprofen, Bifonazole, and LJ570.

Preparation method of para-substituted aryl compound

The invention discloses a preparation method of a para-substituted aryl compound shown as a formula (I) which is described in the specfication. The preparation method is characterized by comprising the following step of: subjecting an aryl sulfonium salt shown as a formula (II) which is described in the specfication and boride to a coupling reaction in a solvent in an inert atmosphere under the action of alkali and a palladium catalyst to obtain the para-substituted aryl compound. According to the method, mono-substituted aromatic hydrocarbon is taken as a substrate, the aryl sulfonium salt isconstructed in situ, and the palladium catalyst catalyzes the aryl sulfonium salt constructed in situ to undergo the Suzuki-Miyaura coupling reaction, so a mono-substituted aromatic hydrocarbon para-arylation or alkenylation product is constructed quickly and efficiently. The method is mild in conditions, high in substrate universality and wide in tolerance of a heterocyclic coupling substrate.

Cyrene as a Bio-Based Solvent for the Suzuki-Miyaura Cross-Coupling

The Suzuki-Miyaura (SM) cross-coupling is the most broadly utilized Pd-catalyzed C-C bond-forming reaction in the chemical industry. A large proportion of SM couplings employ dipolar aprotic solvents; however, current sustainability initiatives and increasingly stringent regulations advocate the use of alternatives that exhibit more desirable properties. Here we describe the scope and utility of the bio-derived solvent Cyrene in SM cross-couplings and evaluate its suitability as a reaction medium for this benchmark transformation from discovery to gram scale.

Dimethylisosorbide (DMI) as a Bio-Derived Solvent for Pd-Catalyzed Cross-Coupling Reactions

Palladium-catalyzed bond-forming reactions, such as the ?-Suzuki-Miyaura and Mizoroki-Heck reactions, are some of the most broadly utilized reactions within the chemical industry. These reactions frequently employ hazardous solvents; however, to adhere to increasing sustainability pressures and restrictions regarding the use of such solvents, alternatives are highly sought after. Here we demonstrate the utility of dimethyl isosorbide (DMI) as a bio-derived solvent in several benchmark Pd-catalyzed reactions: Suzuki-Miyaura (13 examples, 62-100% yield), Mizoroki-Heck (13 examples, 47-91% yield), and Sonogashira (12 examples, 65-98% yield).

GLYCOSIDASE INHIBITORS

Compounds of formula (I) wherein X1, X2, W, R1 to R5, L and m have the meaning according to the claims, are glucosidase inhibitors, and can be employed, inter alia, for the treatment of Alzheimer's disease.

Pd-catalyzed cross-coupling reactions with carbonyls: Application in a very efficient synthesis of 4-aryltetrahydropyridines

A method is proposed to prepare 4-aryltetrahydropyridines by a Pd-catalyzed cross-coupling reaction by using tosylhydrazone as the nucleophilic coupling agent without stoichiometric organometallic reagent. Palladium-catalyzed couplings can be used for the formation of C-C linkages. It was observed during study that tosylhydrazone can be generated by employing 4-piperidones directly in the cross-coupling reaction with tetrahydropyridines in very high yields. It was also found during study that the ketones and aldehydes can be employed as nucleophilic coupling partners in a reaction without using stoichiometric organometallic reagent. The study concluded that the method can be used to prepare different types of di- and trisubstituted olefins at large scale.

Synthesis of 4-substituted tetrahydropyridines by cross-coupling of enol phosphates

Enol phosphates, synthesized from 4-piperidone, react by palladium catalyzed cross-coupling with arylboronic acids and by iron and palladium catalyzed cross-coupling with Grignard reagents to give 4-substituted tetrahydropyridines.

Coupling of arylboronic acids with a partially reduced pyridine derivative

tert-Butylcarbonyl 1,2,3,6-tetrahydro-4-[(trifluoromethyl)sulfonyloxy]pyridine-1-carboxyla te (2) was prepared and underwent palladium-catalyzed coupling reactions with a variety of substituted arylboronic acids 3 to produce a series of tert-butyl-4-aryl-