760-97-4Relevant articles and documents
PROCESS FOR MANUFACTURING A SUBSTITUTED CYCLOHEXANECARBONITRILE
-
, (2021/03/19)
A process for manufacturing a substituted cyclohexanecarbonitrile said process comprising the following steps: - reacting the corresponding substituted cyclohexanecarboxylic acid with thionyl chloride to make the corresponding acyl chloride; and simultaneously or subsequently - reacting the chloride with sulfonamide in sulfolane as solvent to make the substituted cyclohexanecarbonitrile.
Prenylated β-diketones, two new additions to the family of biologically active Hypericum perforatum L. (Hypericaceae) secondary metabolites
Radulovi?, Niko S.,Gen?i?, Marija S.,Stojanovi?, Nikola M.,Randjelovi?, Pavle J.,Baldovini, Nicolas,Kurteva, Vanya
, p. 505 - 513 (2018/06/06)
Two novel β-diketones, 2,6,9-trimethyl-8-decene-3,5-dione (A) and 3,7,10-trimethyl-9-undecene-4,6-dione (B), were identified from the renowned medicinal plant Hypericum perforatum L. The structures of β-diketones A and B were corroborated by syntheses (4 steps starting from methyl acetoacetate, overall yields 30% and 23%, respectively). In solution, these β-diketones predominantly exist as two rapidly interconverting β-keto-enol tautomers. The structures of A and B show some common fragments with the molecules of hyperforin and adhyperforin, respectively, the acknowledged multi-target secondary metabolites from St. John's wort. It is therefore not surprising that A displayed a noteworthy biological activity profile as well (including brine shrimp toxicity, antinociceptive, antidepressant and acetylcholinesterase inhibitory activity). β-Diketone A manifested the most outstanding potency as an acetylcholinesterase inhibitor with IC50 value of 1.51 μM pointing again to the β-keto-enol moiety as a promising lead structure for the development of drugs that could lessen symptoms of Alzheimer's disease (such as dementia, depression and pain).
66. β-Cleavage of Potassium bicyclooct-5-en-2-olates. Stereoselective Synthesis of (+-)-Trichodiene
Snowden, Roger L.,Brauchli, Robert,Sonnay, Philippe
, p. 570 - 593 (2007/10/02)
The transformation of 12 bicyclooct-5-en-2-ols (V or VI) to 3-(cyclohex-3-enyl)-2-alkanones (III or IV), via β-cleavage of their potassium alkoxides in HMPA, has been investigated (cf. table I).As an illustration of this synthetic methodology, a stereoselective synthesis of (+)-trichodiene ((+)-1) is described wich involves the β-cleavage of the tricyclic potassium alkoxides 46a and 47a to cyclopentanone 4 (cf.Scheme 7).