698-39-5Relevant articles and documents
Mechanisms for the alkaline hydrolysis of dibromodifluoromethane-alkene adducts to α,β-unsaturated carboxylates
Elsheimer, Seth,Swanson, JoAnne L.,Gonzalez, Javier
, p. 3 - 9 (2000)
Alternative mechanisms for the title reactions are probed. The previously-reported pathway involving double dehydrobromination to a difluorodiene is operative in at least one case, but this route is specifically excluded for systems that cannot dehydrobrominate to dienes yet still yield carboxylates upon alkaline hydrolysis. Although SN2, SN1, SRN1, and monoelimination-addition processes appear formally possible, an SN2′ mechanism is implicated by studies on model compounds.
A bicyclo[4.2.0]octene-derived monomer provides completely linear alternating copolymers via alternating ring-opening metathesis polymerization (AROMP)
Tan, Li,Parker, Kathlyn A.,Sampson, Nicole S.
, p. 6572 - 6579 (2015/02/19)
Strained bicyclic carbomethoxy olefins were utilized as substrates in alternating ring-opening metathesis polymerization and found to provide low-dispersity polymers with novel backbones. The polymerization of methyl bicyclo[4.2.0]oct-7-ene-7-carboxylate with cyclohexene in the presence of the fast-initiating Grubbs catalyst (H2IMes)(3-Br-Pyr)2Cl2Ru = CHPh leads to a completely linear as well as alternating copolymer, as demonstrated by NMR spectroscopy, isotopic labeling, and gel permeation chromatography. In contrast, intramolecular chain-transfer reactions were observed with [5.2.0] and [3.2.0] bicyclic carbomethoxy olefins, although to a lesser extent than with the previously reported monocyclic cyclobutenecarboxylic ester monomers [Song, A.; Parker, K. A.; Sampson, N. S. J. Am. Chem. Soc. 2009, 131, 3444]. Inclusion of cyclohexyl rings fused to the copolymer backbone minimizes intramolecular chain-transfer reactions and provides a framework for creating alternating functionality in a one-step polymerization.
Structure-activity relationships of unsaturated analogues of valproic acid
Palaty,Abbott
, p. 3398 - 3406 (2007/10/02)
The principal metabolite of valproic acid (VPA), 2-ene VPA, appears to share most of VPA's pharmacological and therapeutic properties while lacking its hepatotoxicity and teratogenicity, thus making it a useful lead compound for the development of safer antiepileptic drugs. Analogues of 2-ene VPA were evaluated for anticonvulsant activity in mice using the subcutaneous pentylenetetrazole test. Cyclooctylideneacetic acid exhibited a potency markedly exceeding that of VPA itself with only modest levels of sedation. Potency, as either ED50 or brain concentration, was highly correlated (r > 0.85) with volume and lipophilicity rather than with one of the shape parameters calculated by molecular modeling techniques, arguing against the existence of a specific receptor site. Instead, a role for the plasma membrane in mediating the anticonvulsant effect is suggested.
