4166-61-4Relevant academic research and scientific papers
Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940
Huffman, John W.,Thompson, Alicia L.S.,Wiley, Jenny L.,Martin, Billy R.
, p. 322 - 335 (2008/04/05)
A series of 1-deoxy analogs of CP-47,497 (8 and 13, n = 0-7) and 1-deoxy analogs of CP-55,940 (9, n = 0-7) have been synthesized and their affinities for the cannabinoid CB1 and CB2 receptors have been determined. Although the majori
Ring Opening of Cyclopropylketones Induced by Photochemical Electron Transfer
Cossy, Janine,Furet, Nathalie,BouzBouz, Samir
, p. 11751 - 11764 (2007/10/02)
Depending on the substitution pattern of cyclopropylketones, the photochemically induced electron transfer of tertiary amines to cyclopropylketones leads either to the formation of 3-substituted cycloalkanones or to ring expanded products.
Iron(III) mediated transformations of trimethylsilyloxy cyclopropyl ethers. Part 2: A new 4-substituted-2-cyclohexenone synthesis
Booker-Milburn,Thompson
, p. 12955 - 12962 (2007/10/02)
Conjugate addition of a variety of Grignard reagents to 2-cyclopentenone gave a number of silyl enol ethers (1) which were treated with Et2Zn/CH2I2 to give the corresponding cyclopropyl silyl ethers (2) in good yield. Ferric chloride ring expansion followed by base elimination of the resulting β-chloro ketones gave the 4-substituted-2-cyclohexenones (4) in moderate to good overall yield. The overall process provides a convenient three step route to these enones from 2-cyclopentenone.
A new 4-substituted-2-cyclohexenone synthesis
Booker-Milburn, Kevin I.,Thompson, David F.
, p. 7291 - 7294 (2007/10/02)
Conjugate addition of a variety of Grignard reagents to 2-cyclopentenone followed by cyclopropanation of the resulting enol ethers gave a range of substituted cyclopropyl silyl ethers in good yield. Treatment of these cyclopropyl silyl ethers with ferric chloride in DMF gave the one carbon ring expanded β-chloro ketones which were eliminated to the corresponding 4-substituted-2-cyclohexenones.
Regiocontrolled Synthesis of Mono-, Di, and Trisubstituted Cyclohexenones by Cycloaddition of Vinyl Sulfones to 1-Methoxy-3--1,3-butadienes. Conversion of Alkenes into Effective Dienophilic Reagents
Kinney, William A.,Crouse, Gary D.,Paquette, Leo A.
, p. 4986 - 5000 (2007/10/02)
Cycloaddition of phenyl vinyl sulfone to Danishefky's diene followed by direct ketalization provided 7, a synthon for the 4-(2-cyclohexenyl) anion.Thus, 7 readily undergoes regiospecific γ-alkylation.Ensuing reductive desulfonylation and hydrolysis provides 2-(and 3-)-cyclohexenones efficiently.Zingiberenol, a monocyclic sesquiterpene, was prepared by means of this methodology.Terminal alkenes and cyclic olefins enter into comparable regiocontrolled Diels-Alder addition if they are first subjected to selenosulfonation and oxidation to the vinyl sulfone.Removal of the phenylsulfonyl substituent after condensation provides the adducts which are formally derived from alkylation of the hypothetical C5 anion of 2-cyclohexenone.The scheme can be expanded to include γ-alkylation prior to desulfonylation.By this means, one is able to prepare 4,5-disubstituted 2-(and 3-)cyclohexenones where the nature of the pendant side chains can be widely varied.
A NEW SYNTHON FOR THE REGIOSPECIFIC γ-ALKYLATION OF 2-CYCLOHEXENONES. APPLICATION TO THE SYNTHESIS OF ZINGIBERENOL AND OXYGENATED BICYCLONONANES
Paquette, Leo A.,Kinney, William A.
, p. 131 - 134 (2007/10/02)
The regiospecific γ-alkylation of γ-sulfonylcyclohexenone ketals is described and applied to various synthetic objectives.
ORGANOMETALLIC COMPOUNDS IN ORGANIC SYNTHESIS-PART 17; REACTIONS OF TRICARBONYLCYCLOHEXADIENYLIRON SALTS WITH O-SILYLATED ENOLATES, ALLYL SILANES AND ASPECTS OF THEIR SYNTHETIC EQUIVALENTS
Birch, Arthur J.,Kelly, Lawrence F.,Narula, Acharan S.
, p. 1813 - 1824 (2007/10/02)
Efficient C-C bond formation results during reactions of O-silylated enolates and allyltrialkylsilanes with a range of tricarbonylcyclohexadienyliron salts to give tricarbonylcyclohexadieneiron complexes in good to excellent yields.This represents a new a
ORGANOMETALLIC COMPOUNDS IN ORGANIC SYNTHESIS. AN EQUIVALENT OF AROMATIC NUCLEOPHILIC SUBSTITUTION BY REACTIONS OF TRICARBONYLCYCLOHEXADIENYLIUMIRON SALTS WITH O-SILYLATED ENOLATES: A NOVEL ARYLATION IN THE 2-POSITION OF CARBONYL COMPOUNDS.
Kelly, Lawrence F.,Narula, Acharan S.,Birch, Arthur J.
, p. 2455 - 2458 (2007/10/02)
Tricarbonylcyclohexadienyliumiron salts are synthetically equivalent to specifically substituted phenyl cations.
