HOME

TheInfoList



Click Here for Items Related To - 1,3-Cyclohexanedione
OR:
1,3-Cyclohexanedione on:   [Wikipedia]   [Google]   [Amazon]

1,3-Cyclohexanedione 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 ...
with the formula (CH2)4(CO)2. It is one of three isomeric cyclohexanediones. It is a colorless compound that occurs naturally. It is the substrate for cyclohexanedione hydrolase. The compound exists mainly as the
enol In organic chemistry, enols are a type of functional group or intermediate in organic chemistry containing a group with the formula (R = many substituents). The term ''enol'' is an abbreviation of ''alkenol'', a portmanteau deriving from "-ene ...
tautomer In chemistry, tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the reloca ...
.


Synthesis, structure, and reactivity

1,3-Cyclohexanedione is produced by semi-
hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...
of
resorcinol Resorcinol (or resorcin) is a phenolic compound. It is an organic compound with the formula C6H4(OH)2. It is one of three isomeric benzenediols, the 1,3-isomer (or ''meta- (chemistry), meta''-isomer). Resorcinol crystallizes from benzene as co ...
: :C6H4(OH)2 + H2 → C6H8O2 1,3-Cyclohexanedione exists in solution predominantly as the
enol In organic chemistry, enols are a type of functional group or intermediate in organic chemistry containing a group with the formula (R = many substituents). The term ''enol'' is an abbreviation of ''alkenol'', a portmanteau deriving from "-ene ...
tautomer In chemistry, tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the reloca ...
. : It reacts under acid catalysis with alcohols to 3-alkoxyenones. Its pKa is 5.26. Treatment of the sodium salt of the enolate with
methyl iodide Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one h ...
gives 2-methyl-1,3-cyclohexanedione, which also exists predominantly as the enol.


Derivatives

Dimedone (5,5-dimethyl-1,3-cyclohexanedione) is a well established reagent. Several herbicides against grasses are formal derivatives of 1,3-cyclohexanedione. Examples of commercial products include cycloxydim, clethodim, tralkoxydim, butroxydim, sethoxydim, profoxydim, and
mesotrione Mesotrione is a herbicide, selective herbicide used mainly in maize crops and has also been shown to have weak insecticidal properties. It is a synthetic compound inspired by the natural substance leptospermone found in the bottlebrush tree ''Cal ...
. 1,3-Cyclohexanedione is also used in the manufacture of
Ondansetron Ondansetron, sold under the brand name Zofran among others, is a medication used to prevent nausea and vomiting caused by chemotherapy, radiation therapy, migraines, or surgery. It is also effective for treating gastroenteritis. It can be giv ...
.


References

{{DEFAULTSORT:Cyclohexanedione, 1,3- Diketones