70120-12-6Relevant articles and documents
A visible-light mediated ring opening reaction of alkylidenecyclopropanes for the generation of homopropargyl radicals
Mao, Ben,Ning, Chao,Shi, Min,Wei, Yin,Zhang, Xiao-Yu
, p. 9088 - 9095 (2021/07/12)
Classical cyclopropylcarbinyl radical clock reactions have been widely applied to conduct mechanistic studies for probing radical processes for a long time; however, alkylidenecyclopropanes, which have a similar molecular structure to methylcyclopropanes, surprisingly have not yet attracted researcher's attention for similar ring opening radical clock processes. In recent years, photocatalytic NHPI ester activation chemistry has witnessed significant blooming developments and provided new synthetic routes for cross-coupling reactions. Herein, we wish to report a non-classical ring opening radical clock reaction using innovative NHPI esters bearing alkylidenecyclopropanes upon photoredox catalysis, providing a brand-new synthetic approach for the direct preparation of a variety of alkynyl derivatives. The potential synthetic utility of this protocol is demonstrated in the diverse transformations and facile synthesis of bioactive molecules or their derivatives and medicinal substances.
A Cannabinoid Derived Prototypical Analgesic
Melvin, Lawrence S.,Johnson, M. Ross,Harbert, Charles A.,Milne, George M.,Weissman, Albert
, p. 67 - 71 (2007/10/02)
The synthesis and analgesic testing of 3-cyclohexanol (1) are described.Prior (SAR) studies led us to conclude that the pyran ring of 9-nor-9β-hydroxyhexahydrocannabinol (HHC) was not necessary for the expression of biological activity in this series of cannabinoids.Analysis of models and the use of molecular mechanics calculations suggested that a simpler compound, such as 1, would possess the biological activity of HHC.Compound 1 was prepared in nine steps from acetonitrile (2).Biological testing in five models of pain shows that compound 1 and morphine are equally potent as analgesics and demonstrates that the pyran ring of HHC is not necessary for biological activity.Further simplification of 1 was pursued by the synthesis of 4--2-pentanol (17), but this derivative exhibits significantly reduced analgesic activity.
3-[2-Hydroxy-4-(substituted)phenyl]-cycloalkanol analgesic agents
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, (2008/06/13)
Cycloalkanones, cycloalkanols and unsaturated analogs thereof, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.