97906-58-6Relevant articles and documents
Umpolung Strategy for Arene C?H Etherification Leading to Functionalized Chromanes Enabled by I(III) N-Ligated Hypervalent Iodine Reagents
Mikhael, Myriam,Guo, Wentao,Tantillo, Dean J.,Wengryniuk, Sarah E.
supporting information, p. 4867 - 4875 (2021/09/14)
The direct formation of aryl C?O bonds via the intramolecular dehydrogenative coupling of a C?H bond and a pendant alcohol represents a powerful synthetic transformation. Herein, we report a method for intramolecular arene C?H etherification via an umpoled alcohol cyclization mediated by an I(III) N-HVI reagent. This approach provides access to functionalized chromane scaffolds from primary, secondary and tertiary alcohols via a cascade cyclization-iodonium salt formation, the latter providing a versatile functional handle for downstream derivatization. Computational studies support initial formation of an umpoled O-intermediate via I(III) ligand exchange, followed by competitive direct and spirocyclization/1,2-shift pathways. (Figure presented.).
Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins
Alkayal, Anas,Buckley, Benjamin R.,Malkov, Andrei V.,Montanaro, Stephanie,Tabas, Volodymyr,Wright, Iain A.
supporting information, (2020/02/13)
The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches. The reported method allows unprecedented direct access to carboxylic acids derived from β,β-trisubstituted alkenes, in a highly regioselective manner.
Novel KV7 ion channel openers for the treatment of epilepsy and implications for detrusor tissue contraction
Seefeld, Mark A.,Lin, Hong,Holenz, Joerg,Downie, Dave,Donovan, Brian,Fu, Tingting,Pasikanti, Kishore,Zhen, Wei,Cato, Matthew,Chaudhary, Khuram W.,Brady, Pat,Bakshi, Tania,Morrow, Dwight,Rajagopal, Sridharan,Samanta, Swapan Kumar,Madhyastha, Naveena,Kuppusamy, Bharathi Mohan,Dougherty, Robert W.,Bhamidipati, Ravi,Mohd, Zainuddin,Higgins, Guy A.,Chapman, Mark,Rouget, Céline,Lluel, Philippe,Matsuoka, Yasuji
supporting information, p. 3793 - 3797 (2018/10/20)
Neuronal voltage-gated potassium channels, KV7s, are the molecular mediators of the M current and regulate membrane excitability in the central and peripheral neuronal systems. Herein, we report novel small molecule KV7 openers that demonstrate anti-seizure activities in electroshock and pentylenetetrazol-induced seizure models without influencing Rotarod readouts in mice. The anti-seizure activity was determined to be proportional to the unbound concentration in the brain. KV7 channels are also expressed in the bladder smooth muscle (detrusor) and activation of these channels may cause localized undesired effects. Therefore, the impact of individual KV7 isoforms was investigated in human detrusor tissue using a panel of KV7 openers with distinct activity profiles among KV7 isoforms. KCNQ4 and KCNQ5 mRNA were highly expressed in detrusor tissue, yet a compound that has significantly reduced activity on homomeric KV7.4 did not reduce detrusor contraction. This may suggest that the homomeric KV7.4 channel plays a less significant role in bladder contraction and further investigation is needed.
Process for the preparation of enantiomerically enriched cyclic beta-aryl or heteroaryl carbocyclic acids
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Page/Page column 21, (2008/06/13)
The present invention relates to a process for the preparation of cis substituted cyclic β-aryl or heteroaryl carboxylic acid derivatives in high diastereo- and enantioselectivity by enantioselective hydrogenation in accordance with the following scheme w
Decarbonylative cross-coupling of cyclic anhydrides: Introducing stereochemistry at an sp3 carbon in the cross-coupling event
O'Brien, Erin M.,Bercot, Eric A.,Rovis, Tomislav
, p. 10498 - 10499 (2007/10/03)
Treatment of cyclic anhydrides with stoichiometric amounts of nickel-neocuproine complex generates alkylcarboxylato-nickelalactones upon extrusion of CO. These metalacycles undergo cross-coupling with arylzinc reagents. The generated CO is sequestered in situ by a nickel-dppb complex. The overall sequence effects a secondary sp3(electrophile)-sp2(nucleophile) cross-coupling and allows for control of stereochemistry during the bond-forming event. Copyright
Design and synthesis of ring-constrained boropeptide thrombin inhibitors
Fevig,Abelman,Brittelli,Kettner,Knabb,Weber
, p. 295 - 300 (2007/10/03)
Ring-constrained boropeptide thrombin inhibitors were designed using information from the X-ray crystal structure of 1 (3-phenylpropionyl-Pro-boroLys-OH · HCl) bound to thrombin. The constraints utilized cyclohexane and pyrrolidine rings to preorganize an aromatic ring in an orientation allowing optimum edge-to-face interaction with the tryptophan 215 side chain located in the S3 specificity pocket of thrombin.
The Copper(I)-Catalyzed Decarboxylation of Malonic Acids; A New Mild and Quantitative Method
Toussaint, Olivier,Capdevielle, Patrice,Maumy, Michel
, p. 1029 - 1031 (2007/10/02)
A novel catalytic decarboxylation of malonic acids under mild conditions is proposed.This simple copper(I)-catalyzed reaction affords the corresponding monocarboxylic acids in good purity and nearly quantitative yields.
Rates of Acid- and Base-Catalyzed Enolization of trans-Hexahydrofluorenone. Concerning Stereoelectronic Control of Enolization
Pollack, Ralph M.,Kayser, Robert H.,Cashen, Michael J.
, p. 3983 - 3987 (2007/10/02)
Rates of both acid-catalyzed and base-catalyzed enolization of trans-hexahydrofluorenone (trans-HHF) have been measured and compared with those for a variety of other ketones.It was found that trans-HHF enolizes substantially faster than cyclohexyl phenyl ketone (CPK) in both acid (1800-fold) and base (2650-fold).This rate variation is thought to be due to two factors. (1) In trans-HHF the cleaving C-H bond is held rigidly parallel to the ? orbital of the ketone.About a factor of 25- to 60-fold is attributed to this stereoelectronic effect. (2) There are stericinteractions in the enol of CPK which decrease its rate of enolization by about 40- to 50-fold.
