3045-98-5Relevant academic research and scientific papers
Potential antitumor agents. Synthesis, reactivity, and cytoxicity of alpha-methylene carbonyl compounds.
Cassady et al.
, p. 815,818 (1978)
The alpha-methylene lactones 9, 12, 21, and 24 were prepared by a mild, convenient alpha-methylenation process using the alpha-ethyloxalyl derivatives in nonoptimized yields ranging from 23 to 90%. The rates of reaction of these and several other lactones with cysteine at pH 7.4 and their KB toxicities were measured. These studies showed that neither the strained trans-fused alpha-methylene lactone 12 nor the hydroxy-alpha-methylene lactones 5 and 6 reacted with cysteine with rates comparable to elephantopin. Based on these limited studies, the rate of cysteine addition appears to be relatively insensitive to changes in strain energy and neighboring groups. In addition, the rate constant for reaction with cysteine did not correlate with cytotoxicity.
Spiro-compound, and preparation method and application thereof
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Paragraph 0111; 0122, (2017/02/17)
The invention relates to the fields of medicinal chemistry and pharmacotherapeutics, and discloses a spiro-compound as shown in the following general formula, and a preparation method and application thereof. A bioactivity screening result shows that the
Diastereoconvergent negishi cross-coupling using functionalized cyclohexylzinc reagents
Moriya, Kohei,Knochel, Paul
supporting information, p. 924 - 927 (2014/03/21)
Highly diastereoselective Pd-catalyzed cross-coupling reactions of functionalized 2-, 3-, and 4-substituted cyclohexylzinc reagents with aryl, heteroaryl, and alkenyl iodides have been performed under mild conditions. The use of Ruphos (2-dicyclohexylphos
The enantioselective synthesis of tetracyclic methyllycaconitine analogues
Sparrow, Kevin,Barker, David,Brimble, Margaret A.
experimental part, p. 7989 - 7999 (2011/11/07)
A new enantioselective synthesis of ABEF ring analogues of methyllycaconitine has been developed using a chiral cobalt(III) salen-catalyzed Diels-Alder reaction to form the B ring. Subsequent elaboration to form the A, E and F rings was achieved by sequential Dieckmann, Mannich and Wacker-type cyclizations to afford tetracyclic analogues in 97.5% ee.
Cascade synthesis of (E)-2-alkylidenecyclobutanols
Falck,Bandyopadhyay, Anish,Puli, Narender,Kundu, Abhijit,Reddy, L. Manmohan,Barma, Deb K.,He, Anyu,Zhang, Hongming,Kashinath, Dhurke,Baati, Rachid
supporting information; experimental part, p. 4764 - 4766 (2009/12/27)
A facile, one-pot reaction cascade condenses 1,1,1-trichloroalkanes with α,β-unsaturated ketones to unexpectedly furnish moderate to good yields of (E)-2-alkylidenecyclobutanols.
Efficient α-methylenation of carbonyl compounds in ionic liquids at room temperature
Vale, Juliana A.,Zanchetta, Daniel F.,Moran, Paulo J. S.,Rodrigues, J. Augusto R.
experimental part, p. 75 - 78 (2009/05/30)
The application of several 1-butyl-3-methylimidazolium (BMIM) salt ionic liquids as solvent in the α-methylenation of carbonyl compounds at room temperature is reported. The ionic liquid [BMIM][NTf2] gave a clean reaction in a short time and good yields of several α-methylene carbonyl compounds. This ionic liquid was reused without affecting the reaction rates or yields over seven runs. Georg Thieme Verlag Stuttgart.
Oxidation of silyl enol ethers by using IBX and IBX·N-oxide complexes: A mild and selective reaction for the synthesis of enones
Nicolaou,Gray, David L. F.,Montagnon, Tamsyn,Harrison, Scott T.
, p. 996 - 1000 (2007/10/03)
α,β-Unsaturated carbonyl compounds can be prepared by the oxidation of trimethylsilyl enol ethers with IBX (1) or IBX·MPO (2). A diverse set of carbonyl compounds can be dehydrogenated with ease by using this method. Trimethylsilyl enol ethers such as 4, which are formed in situ by the addition of an organometallic species to an enone, can be dehydrogenated with 1 or 2 to give a functionalized enone (e. g. 3 → 5). IBX = iodoxybenzoic acid; MPO = 4-methoxypyridine-N-oxide.
Effect of cyclohexenonic long chain fatty alcohols on neurite outgrowth. Study on structure-activity relationship
Girlanda-Junges, Celine,Keyling-Bilger, Florence,Schmitt, Gaby,Luu, Bang
, p. 7735 - 7748 (2007/10/03)
Four series of long chain fatty alcohols bearing a cyclohexenone moiety in addition to a ω-alkanol side chain were synthesized using 'Umpolung' reactivity strategy. Their effect on neurite outgrowth was evaluated by means of fetal rat neurons in culture. The length of the ω-hydroxy side chain is a crucial factor for biological activity.
Metal-Catalyzed Oxidations with Pinane Hydroperoxide: A Mechanistic Probe to Distinguish between Oxometal and Peroxometal Pathways
Lempers,Ripolles i Garcia,Sheldon
, p. 1408 - 1413 (2007/10/03)
The relative reactivities of tert-butyl hydroperoxide (TBHP) and pinane hydroperoxide (PHP) in metal (Cr, Mo, Ru, Se, V, and Zr)-catalyzed oxidations were compared. When these oxidations involve rate-limiting oxygen transfer from a peroxometal species to the substrate huge differences between TBHP and PHP were observed, e.g., molybdenum-catalyzed epoxidation of cyclohexene with TBHP gave a 98% yield while PHP gave 0%. When the reaction involves reaction of an oxometal species with the substrate as the rate-limiting step, little or no difference is observed, e.g., the selenium-catalyzed allylic oxidation of β-pinene gave a 96% and 99% yield with TBHP and PHP, respectively. Small but significant differences are observed when reoxidation of the catalyst by the hydroperoxide to the active oxometal species is the rate-limiting step; e.g., the chromium-catalyzed oxidation of carveol gave carvone in 89% and 24% yield with TBHP and PHP, respectively. Hence, the effect of RO2H structure on rate is dependent on the rate-limiting step.
Regioselectivity of the Singlet Oxygen Ene Reaction (Schenck Reaction) with Vinylsilanes
Adam, Waldemar,Richter, Markus J.
, p. 3335 - 3340 (2007/10/02)
The ene reaction of singlet oxygen and vinylsilanes 1 with various substitution patterns and double-bond geometry has been studied. β-Silyl allylic hydroperoxides 2 were the major products of the photooxygenation, accompanied by smaller amounts of α,β-unsaturated ketones 3.The latter derive from decomposition of the regioisomeric α-hydroperoxy silanes 4 by elimination of silanol.Regioselectivities up to 97:3 were observed for vinylsilanes with a methyl group geminal to the silyl group and with cyclic derivatives.Z-Configurated substrates showed lower regioselectivity and reactivity.Elongation of the carbon chain at the geminal position also increased the amount enone formed.These results are rationalized in terms of stereoelectronic effects imposed by the silyl group on the ring-opening of the perepoxide intermediate.
