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A Michael reaction is used as a mechanistic step by many covalent inhibitor drugs. Cancer drugs such as ibrutinib, osimertinib, and rociletinib have an acrylamide functional group as a Michael acceptor. The Michael donor on the drug reacts with a Michael acceptor in the active site of an enzyme. This is a viable cancer treatment because the ...
NEM is a Michael acceptor in the Michael reaction, which means that it adds nucleophiles such as thiols. The resulting thioether features a strong C-S bond and the reaction is virtually irreversible. Reaction with thiols occur in the pH range 6.5–7.5, NEM may react with amines or undergo hydrolysis at a more alkaline pH.
Methyl acrylate is a classic Michael acceptor, which means that it adds nucleophiles at its terminus. For example, in the presence of a base catalyst, it adds hydrogen sulfide to give the thioether: [21] 2 CH 2 CHCO 2 CH 3 + H 2 S → S(CH 2 CH 2 CO 2 CH 3) 2. It is also a good dienophile.
The Stork enamine alkylation involves the addition of an enamine to a Michael acceptor (e.g., an α,β -unsaturated carbonyl compound) or another electrophilic alkylation reagent to give an alkylated iminium product, which is hydrolyzed by dilute aqueous acid to give the alkylated ketone or aldehyde. [1]
In the Michael reaction, the ketone is deprotonated by a base to form an enolate nucleophile which attacks the electron acceptor (in red). This acceptor is generally an α,β-unsaturated ketone, although aldehydes, acid derivatives and similar compounds can work as well (see scope). In the example shown here, regioselectivity is dictated by the ...
The sp 2 lone pair acts as an electron donor, whereas the empty p-orbital is capable as acting as an electron acceptor. In this example, the β-carbon of the α,β-unsaturated ester 1 formally acts as a nucleophile, [4] whereas normally it would be expected to be a Michael acceptor. Scheme 3. Umpolung of Michael Acceptors
Keegan-Michael Key has a ton of options when it comes to picking a favorite Key & Peele sketch. But he has a clear winner — and Halloween is the time to revisit it. “It's such a silly sketch ...
In addition to standard nucleophilic addition reactions on the C=C bond, nitroethylene can serve as a Michael acceptor in a Michael addition reaction. A typical Michael donor (i.e. ketone or aldehyde) can be used. [8] Like most nitro compounds, a platinum/palladium catalyzed reaction with hydrogen gas can reduce the nitro group to an amine group.