17356-28-4

Usage

Use

Synthesis of pharmaceutical drugs and natural products

Structure

Cyclic amide with a six-membered ring containing nitrogen and oxygen

Physical Properties

Colorless to pale yellow liquid with a slightly sweet and nutty odor

Applications

Potential use in the pharmaceutical industry, of interest to researchers for its chemical and biological properties

Upstream product

• 105-60-2 caprolactam 
• 106-95-6 allyl bromide 
• 92954-34-2 O-allyl-N,N'-dicyclohexyl isourea 
• 1606141-55-2 2-(anthracen-9-yl)ethyl 6-(allylamino)hexanoate 
• 1606141-51-8 2-(anthracen-9-yl)ethyl 6-(allyl(tert-butoxycarbonyl)amino)hexanoate 
• 1606141-48-3 6-(allyl(tert-butoxycarbonyl)amino)hexanoic acid 

Downstream Products

• 105-60-2 caprolactam 
• 222048-38-6 2-[1-Allyl-azepan-(2E)-ylidene]-1-(4-chloro-phenyl)-ethanone 

Relevant academic research and scientific papers

Thermally induced substrate release via intramolecular cyclizations of Amino esters and Amino carbonates

The relative cleavage of an alcohol from a panel of amino esters and amino carbonates via intramolecular cyclization was examined as a mechanism for substrate release. Thermal stability at 37 °C was observed only for the seven-membered ring progenitors. Applicability of the approach was illustrated by δ-lactam formation within a poly(dimethylsiloxane) microchannel for release of a captured fluorescent probe.

Hydrolytic deallylation of N-allyl amides catalyzed by PdII complexes

Hydrolytic deallylation of N-allyl amides to give amides and propanal can be achieved with PdII catalysts. The optimized catalyst consists of Pd(OCOCF3)2 and 1,3-bis(diphenylphosphanyl) propane (DPPP). Several kinds of open-chain N-allyl amides and N-allyl lactams undergo hydrolytic deallylation to give the corresponding amides and lactams in good to high yield. A mechanism which includes isomerization to enamides and subsequent hydrolysis is proposed. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congeners

A convenient methodology for the deprotection of N-allylic amide-like moieties was developed. The first examples accounting for the ruthenium-catalyzed deallylation of amides, lactams, imides, pyrazolidones, hydantoins, and oxazolidinones have been achieved by the sequential use of Grubbs carbene (isomerization step) and RuCl3 (oxidation step). A variety of substrates, including enantiopure multifunctional β- and γ-lactams, can be employed.

Direct N-Allylation of Amides with 2-Allylisourea Catalyzed by Palladium(0)

Direct N-allylation of amides catalyzed by palladium(0) complexes took place under neutral conditions by the use of 2-allylisourea as the allylating agent.