123121-31-3Relevant academic research and scientific papers
Auxiliary-enabled Pd-catalyzed direct arylation of methylene C(sp 3)-H bond of cyclopropanes: Highly diastereoselective assembling of Di- and trisubstituted cyclopropanecarboxamides
Parella, Ramarao,Gopalakrishnan, Bojan,Babu, Srinivasarao Arulananda
, p. 3238 - 3241 (2013/07/26)
An auxiliary-enabled and Pd(OAc)2-catalyzed direct arylation of C(sp3)-H bonds of cyclopropanes and production of di- and trisubstituted cyclopropanecarboxamides having contiguous stereocenters are reported. The installation of aryl groups on cyclopropanecarboxamides led to the assembling of novel mono- and di- aryl-N-(quinolin-8-yl)cyclopropanecarboxamide scaffolds and mono- and di- aryl-N-(2-(methylthio)phenyl) cyclopropanecarboxamides. The stereochemistry of products was unequivocally assigned from the X-ray structures of key compounds.
Trans N-Methyl-N-[2-(1-pyrrolidinyl)cyclohexyl] cycloprop-2-ene-1-carboxamides: Novel lipophilic kappa opioid agonists
Sabin,Horwell,McKnight,Broqua
, p. 291 - 296 (2007/10/03)
The synthesis and kappa opioid agonist activities of some lipophilic analogues of the kappa opioid agonist U-50488 incorporating motifs bearing two aromatic rings in place of the 3,4-dichlorophenyl group are described. Trans 2,3-diphenyl-N-methyl-N[2-(1-pyrrolidinyl)cyclohexyl]-2-cyclopropene-1 -carboxamide, 7, is a potent kappa opioid agonist. A diphenylcyclopropene analogue of CI-977, trans 2,3-diphenyl-N-methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]-2 -cyclopropene-1-carboxamide, 13, is a highly lipophilic chemically novel potent selective kappa opioid agonist.
Electron Demand in the Transition State of the Cyclopropylidene to Allene Ring Opening
Warner, Philip,Sutherland, Robert
, p. 6294 - 6300 (2007/10/02)
The electronic structure of the transition state for the cyclopropylidene to allene conversion has been probed.The methodology involved the relative rates of ring opening vs trapping by MeOH for a series of variously substituted 2,3-diarylcyclopropylidenes.With the assumption that the rate of trapping was unaffected by substituents, a Hammett correlation was constructed.The negative value (-0.72) for ρ indicated that the carbenic center attracts electron density in the ring-opening transition state, much like the cyclopropyl cation to allyl cation transition state.Temperature-dependent studies showed that the observed preference for ring opening was driven by entropy factors.Also, using reasonable estimates for the close to diffusion-controlled trapping activation enthalpies, the derived enthalpies for ring opening were in close agreement with the best theoretical values.
New Host Family Based on Small-Ring Compounds
Weber, Edwin,Hecker, Manfred,Csoeregh, Ingeborg,Czugler, Matyas
, p. 7866 - 7872 (2007/10/02)
Three- and four-membered ring compounds with functional groups and bulky substituents have proved to be a rewarding new source of inclusion hosts.These hosts form clathrates with a variety of uncharged organic molecules ranging from protic dipolar to apolar compounds (168 different inclusion species).Formation and selectivity depend in a systematic manner on structural parameters of the host, such as the nature, number, and position of functional groups, the substituents, and ring size.X-ray structure analyses of two inclusion compounds 12121; = 9.782 (1), b = 11.376 (1), c = 17.603 (1) Angstroem; Z = 4. 17*MeCN (1:1): Pbcn; a = 12.314 (1), b = 16.074 (1), c = 12.938 (1) Angstroem; Z = 4> and of a free host molecule 1; a = 7.339 (2), b = 11.657 (4), c = 9.149 (3) Angstroem; β = 110.070; Z = 2> are reported, revealing the building principles of the new clathrate family.The structures exhibit linear chains of inter-/intramolecular H bridges between carboxylic groups in the free host 1 and H-bridge aggregation of host and guest molecules in infinite helical chains for the 1*t-BuOH (1:1) inclusion.In 17*MeCN (1:1), the guest molecules are tightly enclosed by the host framework without further specific interactions.
Stereochemistry of the transformations of gem-cyclopropanedicarboxylic acid to carboxybutyrolactones. II. Stereospecificity of the rearrangement of 2,3-diphenyl- and 2-methyl-3-phenyl-1,1-cyclopropanedicarboxylic acids
Mandel'shtam, T. V.,Kolesova, S. V.,Polina, T. V.,Solomentsev, V. V.,Osmolovskaya, N. S.
, p. 1024 - 1031 (2007/10/02)
When heated above melting points, cis- and trans-2,3-diphenyl-1,1-cyclopropanedicarboxylic acids lose carbon dioxide and are converted nonstereospecifically into a mixture of trans-3,4-diphenyl-γ-butyrolactone and trans-2,3-diphenyl-1-cyclopropanecarboxyl
