20299-80-3

Usage

Type of compound

Ketone

Presence of heterocyclic ring

Pyrrolidine ring

Explanation

A five-membered heterocyclic ring containing one nitrogen atom.

Explanation

Due to its pleasant odor.

Explanation

As a precursor for the synthesis of various biologically active compounds.

Application in perfumes and fragrances

Commonly used

Application in the food industry

Used as a flavoring agent

Pharmaceutical potential

Studied for its potential pharmaceutical applications

Upstream product

• 123-75-1 pyrrolidine 
• 6304-39-8 caprylic hydrazide 
• 111-64-8 n-octanoic acid chloride 
• 1119-57-9 N-methyloctanoylamide 
• 15567-46-1 N-methyl-N-nitrosooctanoylamide 
• 124-07-2 Octanoic acid 

Downstream Products

• 111-87-5 octanol 
• 140172-39-0 1-Butylamino-5-methyl-2,4,6,8-tetraoxo-3,7-dioxa-2λ⁵,4λ⁵,6λ⁵,8λ⁵-tetraphospha-bicyclo[3.3.1]nonane-2,4,6,8-tetraol 
• 145336-44-3 Bicyclic 1-butylaminodecane-1,1,3,3-tetrayl-tetrakis-phosphonic anhydride aniline salt 
• 30711-41-2 1-(thiophen-2-yl)octan-1-one 

Relevant academic research and scientific papers

Method for preparing amide compound by photocatalysis of nitrogen-containing heterocyclic compound

The invention provides a method for preparing an amide compound by photocatalysis of a nitrogen-containing heterocyclic compound. The method comprises the following steps: mixing the nitrogen-containing heterocyclic compound, organic carboxylic acid and tetrahalomethane in a solvent, adding a catalyst, and reacting under the illumination condition to prepare the amide compound. According to the invention, the organic carboxylic acid, the nitrogen-containing heterocyclic compound containing reactive hydrogen on nitrogen atoms and the tetrahalomethane are used as raw materials, so the raw materials are wide in source, low in cost and high in safety, and large-scale production is facilitated; the halogen simple substance is co-produced in the reaction process, the added value is high, a large amount of waste is prevented from being generated, and the method has high atom economy and environmental friendliness; light conditions are adopted to replace traditional heating and high-pressure conditions, the reaction conditions are mild, environmental pollution is reduced, and the reaction cost is reduced; the method has the advantages of good substrate applicability, mild process conditions, environmental protection, simple process, simple and feasible operation method, and facilitation of popularization and application.

A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects

We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.

Tert -Butyl nitrite promoted transamidation of secondary amides under metal and catalyst free conditions

A mild and efficient method is demonstrated for the transamidation of secondary amides with various amines including primary, secondary, cyclic and acyclic amines in the presence of tert-butyl nitrite. The reaction proceeds through the N-nitrosamide intermediate and provides the transamidation products in good to excellent yields at room temperature. Moreover, the developed methodology does not require any catalyst or additives.

Synthesis and biological evaluation of new analogues of the active fungal metabolites N-(2-methyl-3-oxodecanoyl)-2-pyrroline and N-(2-methyl-3- oxodec-8-enoyl)-2-pyrroline

To evaluate the effect of simplifying the β-ketoamide system present in active isolated metabolites from Penicillium brevicompactum (2 and 3) on the activity, new analogues with a monocarbonylic amide functionality have been obtained. In this way, the insecticidal and fungicidal activities have been improved in relation to the natural products taken as lead molecules. Thus, two of the synthetic analogues (5a and 5b) showed very important insecticidal activities against third-instar nymphs of Oncopeltus fasciatus Dallas, with acute LD50 values of 3.0 and 1.5 μg/cm2, respectively. Moreover, some analogues showed good levels of fungicidal activity against a wide range of commercially important and taxonomically diverse fungi; remarkably, compound 7c has proved to be highly active against Colletotrichum gloesporoides and Colletotrichum coccodes, with ED50 values of 2.04 and 11.7 μg/mL, respectively.

Dermal penetration enhancement profile of hexamethylenelauramide and its homologues: In vitro versus in vivo behavior of enhancers in the penetration of hydrocortisone

Several amides of cyclic amines were prepared and tested as penetration enhancers in the diffusion of various drugs through hairless mouse skin in vitro. Hexamethylenelauramide (hexahydro-1-lauroyl-1H-azepine) was selected as a broad spectrum penetration enhancer worthy of further study. Later, the duration of the effect of various enhancers on the penetration barrier in vivo was determined by evaluating the in vitro diffusion of hyrocortisone through skins that had been pretreated in vivo. We found that the longer the pretreatment, the smaller the amount of penetrated hydrocortisone. Furthermore, our results suggested that differences exist in the retention of various enhancers in living mouse skin. The in vitro pretreatment experiments revealed that the penetration through dead skin is slow compared with the penetration through living skin. Neither the nature of the receptor phase, nor the increased temperature of the in vitro experiments, explain the striking differences between the in vivo and the in vitro experiments. Finally, the penetration of hydrocortisone through the stratum corneum in the presence of enhancers, as well as the penetration of 1-dodecylhexahydro-2H-azepin-2-one (laurocapram), hexamethylenelauramide, and oleic acid, were determined using a stratum corneum stripping technique. More hydrocortisone penetrated through the stratum corneum during the first 3 h in the presence of hexamethylenelauramide than in the presence of laurocapram or oleic acid.

FACILE OXIDATIVE CONVERSION OF HYDRAZIDES OF CARBOXYLIC ACIDS TO CORRESPONDING ACIDS, ESTERS AND AMIDES USING COPPER COMPOUNDS

Oxidative conversion of hydrazides of carboxylic acids to acids, esters and amides using Cu salts was studied.Acids were obtained in high yields by using a catalytic amount of Cu(OAc)2 at room temperature by bubbling oxygen.Hydrazides were converted to esters by the treatment with Cu(OR)Cl or Cu(OR)2 formed in situ from CuCl2 and sodium alkoxide.Amides were obtained in high yields by the oxidation of hydrazides with CuCl2 in the presence of amines.