112422-44-3Relevant academic research and scientific papers
Polylithiumorganic compounds. Part 29: C,C Bond cleavage of phenyl substituted and strained carbocycles using lithium metal
Maercker, Adalbert,Oeffner, Kristian S.,Girreser, Ulrich
, p. 8245 - 8256 (2007/10/03)
The reaction of phenyl substituted cyclopropanes phenylcyclopropane and 1,1-diphenylcyclopropane, phenyl substituted bicyclobutanes 1- phenylbicyclobutane, 1-methyl-3-phenylbicyclobutane, 1-methyl-2,2- diphenylbicyclobutane, as well as phenyl substituted spiropentanes phenylspiropentane and 1,1-diphenylspiropentane with lithium metal or lithium di-t-butylbiphenyl (LiDBB) was investigated. Under suitable reaction conditions and choice of solvent in all cases cleavage of the single bond next to the activating phenyl group was observed. The dilithiumorganic compounds thus obtained are sufficiently stable and can be trapped with electrophiles. Lithium hydride elimination is observed as follow-up reaction only in a few cases. The corresponding anions of the strained ring systems 1-lithio-2,2- diphenylcyclopropane, 1-lithio-3-phenylbicyclobutane, 1-lithio-3-methyl-2,2- diphenylbicyclobutane, and 1-lithio-4-phenylspiropentane, which can be obtained by lithium bromine exchange or by metalation of the unsubstituted carbocycle, do not show any cleavage upon reaction with lithium metal. The reaction of phenyl substituted cyclopropanes, bicyclobutanes as well as spiropentanes with lithium metal with formation of highly reactive dilithiumorganic compounds was investigated. In all cases cleavage of the bond next to the phenyl substituent(s) was observed.
Piperazinebenzylamines as potent and selective antagonists of the human melanocortin-4 receptor
Pontillo, Joseph,Tran, Joseph A.,Fleck, Beth A.,Marinkovic, Dragan,Arellano, Melissa,Tucci, Fabio C.,Lanier, Marion,Nelson, Jodie,Parker, Jessica,Saunders, John,Murphy, Brian,Foster, Alan C.,Chen, Chen
, p. 5605 - 5609 (2007/10/03)
SAR studies of a series of piperazinebenzylamines resulted in the discovery of potent antagonists of the human melanocortin-4 receptor. Compounds 11c, 11d, and 11l, which had Ki values of 21, 14, and 15 nM, respectively, possessed low efficacy
CYCLOBUTANEDIYLS: A NEW CLASS OF LOCALIZED BIRADICALS. SYNTHESIS AND EPR SPECTROSCOPY.
Jain,Sponsler,Coms,Dougherty
, p. 1356 - 1366 (2007/10/11)
Nine triplet cyclobutanediyls (1) have been synthesized and observed by matrix isolation EPR spectroscopy. The zero-field splitting (zfs) parameters provide detailed information on the spin densities in these structures. The observed zfs values can be quantitatively modeled by using a straightforward semiempirical scheme, as long as one explicitly incorporates the spin polarization effects known to be important in radicals such as allyl and benzyl. In addition, interpretable hyperfine coupling (hfc) has been observed in many cyclobutanediyls. Spectral simulation produces the hfc constants, which provide further information on spin distribution and indicate that the four-membered ring in 1 is planar.
