Ynone on:
[Wikipedia]
[Google]
[Amazon]
In
An alternative is the direct coupling of an 
Other methods utilize an oxidative cleavage of an
In organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...
, an ynone is an organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
containing a ketone
In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...
() functional group
In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...
and a triple bond
A triple bond in chemistry is a chemical bond between two atoms involving six Electron pair bond, bonding electrons instead of the usual two in a covalent bond, covalent single bond. Triple bonds are stronger than the equivalent covalent bond, sin ...
. Many ynones are α,β-ynones, where the carbonyl
In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double bond, double-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such a ...
and alkyne
\ce
\ce
Acetylene
\ce
\ce
\ce
Propyne
\ce
\ce
\ce
\ce
1-Butyne
In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and n ...
groups are conjugated. Capillin is a naturally occurring example. Some ynones are not conjugated.
Synthesis of α,β-ynones
One method for synthesizing ynones is the acyl substitution reaction of an alkynyldimethylaluminum with anacyl chloride
In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example o ...
. An alkynyldimethylaluminum compound is the reaction product of trimethylaluminum
Trimethylaluminium or TMA is one of the simplest examples of an organoaluminium compound. Despite its name it has the formula (abbreviated as , where Me stands for methyl), as it exists as a dimer. This colorless liquid is pyrophoric. It is an i ...
and a terminal alkyne
\ce
\ce
Acetylene
\ce
\ce
\ce
Propyne
\ce
\ce
\ce
\ce
1-Butyne
In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and n ...
.
An alternative is the direct coupling of an acyl chloride
In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example o ...
with a terminal alkyne, using a copper-based nanocatalyst:
Other methods utilize an oxidative cleavage of an aldehyde
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...
, followed by reaction with a hypervalent alkynyl iodide, using a gold catalyst.
An alternative but longer synthetic method involves the reaction of an alkynyllithium compound with an aldehyde. The reaction produces a secondary alcohol that then can be oxidized via the Swern oxidation
In organic chemistry, the Swern oxidation also known as Moffatt-Swern, named after Daniel Swern, is a chemical reaction whereby a primary or secondary Alcohol (chemistry), alcohol () is redox, oxidized to an aldehyde () or ketone () using oxalyl ...
.
Synthesis of β,γ- and γ,δ-ynones
Terminal alkynes add across α,β-unsaturated ketones in the presence of palladium catalysts. The reaction affords γ,δ-ynones. Terminal alkynes add across epoxides to given yneols, which can be oxidized to give β,γ-ynones.Further reading
*Bis-ynones can undergo an intramolecularcycloaddition
In organic chemistry, a cycloaddition is a chemical reaction in which "two or more Unsaturated hydrocarbon, unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of th ...
to form furan
Furan is a Heterocyclic compound, heterocyclic organic compound, consisting of a five-membered aromatic Ring (chemistry), ring with four carbon Atom, atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as f ...
derivatives.
See also
*Diketone
In organic chemistry, a dicarbonyl is a molecule containing two carbonyl () groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls ...
References
External links
* {{Functional group Functional groups Ketones Alkyne derivatives