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The chronic toxicity of hexane is attributed to hexane-2,5-dione. The symptoms are tingling and cramps in the arms and legs, followed by general muscular weakness. In severe cases, atrophy of the skeletal muscles is observed, along with a loss of coordination and vision problems. [2] Similar symptoms are observed in animal models.
Amarnath's work showed that the diastereomers of 3,4-disubstituted-2,5-hexane diones react at different rates. In the commonly accepted mechanism, these diones would go through a common enol intermediate, meaning that the meso and d,l -racemic isomers would cyclize at the same rate as they form from a common intermediate.
This reaction is an important approach to the formation of carbon-carbon bonds in organic molecules containing ring systems. As an example, under strong basic conditions (e.g. sodium hydroxide), hexane-2,5-dione (compound A in Figure 1) can cyclize via intramolecular aldol reaction to form the 3-methylcyclopent-2-en-1-one (compound B).
Hexane-2,5-dione; Hydromadinone; Hydromadinone acetate; 2-Hydroxy-3-methyl-2-cyclopenten-1-one; Hydroxydione; Hydroxyprogesterone caproate; Hydroxyprogesterone heptanoate; 11α-Hydroxyprogesterone; 11β-Hydroxyprogesterone; 16α-Hydroxyprogesterone; 17α-Hydroxyprogesterone
The compound is prepared by base-catalyzed condensation of 1-hydroxyhexane-2,5-dione, a derivative of hydroxymethylfurfural. [2] The structure has been confirmed by X-ray crystallography. [2] Quantum calculations also indicate that the enol is strongly favored relative to the diketo tautomer.
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2,5-Dimethylthiophene is an organosulfur compound with the formula C 4 H 2 (CH 3) 2 S. It is one of four isomers of dimethylthiophene. A colorless liquid, it is prepared by sulfurization of hexane-2,5-dione. [1] It is approved as a food flavouring additive in Europe. [2]
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