108-55-4Relevant articles and documents
Lactones as minor products of the electrochemical reduction of glutaryl dichloride at mercury cathodes in acetonitrile
Urove, Greg A.,Peters, Dennis G.
, p. 1271 - 1274 (1993)
Electrochemical reduction of glutaryl dichloride at a mercury electrode in acetonitrile containing 0.1 M tetraethylammonium perchlorate results in the formation of 5-chlorovalerolactone, valerolactone, and a polymeric species.
Remote stereocontrol as a synthetic strategy: Diastereoselective annulations on an arene tricarbonylchromium template
Sur, Surojit,Ganesh, Sambasivam,Puranik, Vedavati G.,Sarkar, Amitabha
, p. 977 - 982 (1998)
Stereoselective annulations on Cr(CO)3 complexed tetralone and benzosuberone derivatives have been achieved. Diastereomeric products are shown to be related by an epimerisable chiral centre. An unusually facile de-ethoxycarbonylation has been observed.
A NEW SYNTHESIS OF CARBOXYLIC AND CARBONIC ACID ANHYDRIDES USING PHASE TRANSFER REACTIONS
Plusquellec, Daniel,Roulleau, Fabienne,Lefeuvre, Martine,Brown, Eric
, p. 2471 - 2476 (1988)
Acyl chlorides and alkylchloroformates smoothly reacted with one molar equivalent of sodium hydroxide, using liquid-liquid phase transfer conditions to afford high yields of the corresponding symmetrical carboxylic and carbonic hemiester anhydrides.Unstable anhydrides such as 4-nitrobenzoic, 2-furoic and methacrylic anhydrides, which are otherwise difficult to obtain, were easily prepared by this method.The reaction mechanism does not seem to involve intermediate hydrolysis of half the acid chloride into the corresponding sodium carboxylate.
METHOD FOR PRODUCING CARBOXYLIC ACID ANHYDRIDE OR SULFONIC ACID ANHYDRIDE
-
Paragraph 0042-0045; 0048-0049, (2021/02/25)
To provide a method for producing carboxylic acid anhydride or sulfonic acid anhydride in which carboxylic acid anhydride or sulfonic acid anhydride is produced in a simple or easy process using carboxylic acid or sulfonic acid as raw material, and using an industrially available raw material and in an efficient process in industrial practice.SOLUTION: Provided is a method for producing carboxylic acid anhydride or sulfonic acid anhydride, which is a method for producing an acid anhydride by reacting carboxylic acid or sulfonic acid and a halogenating agent, and in which a solvent containing a phosphoric acid ester such as the formula (1) is used. (R1, R2 and R3 are the same or non-identical alkyl group or fluorine-containing alkyl group having 1 to 10 carbon atoms, and at least one is fluorine-containing alkyl group.).SELECTED DRAWING: None
Heterogeneous catalysts for the cyclization of dicarboxylic acids to cyclic anhydrides as monomers for bioplastic production
Rashed, Md. N.,Siddiki,Ali, Md. A.,Moromi, Sondomoyee K.,Touchy, Abeda S.,Kon, Kenichi,Toyao, Takashi,Shimizu, Ken-Ichi
, p. 3238 - 3242 (2017/07/28)
Cyclic anhydrides, key intermediates of carbon-neutral and biodegradable polyesters, are currently produced from biomass-derived dicarboxylic acids by a high-cost multistep process. We present a new high-yielding process for the direct intramolecular dehydration of dicarboxylic acids using a reusable heterogeneous Lewis acid catalyst, Nb2O5·nH2O. Various dicarboxylic acids, which can be produced by a biorefinery process, are transformed into the corresponding cyclic anhydrides as monomers for polyester production. This method is suitable for the production of renewable polyesters in a biorefinery process.
4-Biphenylalanine- and 3-Phenyltyrosine-Derived Hydroxamic Acids as Inhibitors of the JumonjiC-Domain-Containing Histone Demethylase KDM4A
Morera, Ludovica,Roatsch, Martin,Fürst, Michael C. D.,Hoffmann, Inga,Senger, Johanna,Hau, Mirjam,Franz, Henriette,Schüle, Roland,Heinrich, Markus R.,Jung, Manfred
, p. 2063 - 2083 (2016/10/22)
Overexpression of the histone lysine demethylase KDM4A, which regulates H3K9 and H3K36 methylation states, has been related to the pathology of several human cancers. We found that a previously reported hydroxamate-based histone deacetylase (HDAC) inhibitor (SW55) was also able to weakly inhibit this demethylase with an IC50value of 25.4 μm. Herein we report the synthesis and biochemical evaluations, with two orthogonal in vitro assays, of a series of derivatives of this lead structure. With extensive chemical modifications on the lead structure, also by exploiting the versatility of the radical arylation with aryldiazonium salts, we were able to increase the potency of the derivatives against KDM4A to the low-micromolar range and, more importantly, to obtain demethylase selectivity with respect to HDACs. Cell-permeable derivatives clearly showed a demethylase-inhibition-dependent antiproliferative effect against HL-60 human promyelocytic leukemia cells.
Reactions of hydrogen peroxide with acetylacetone and 2- acetylcyclopentanone
Novikov,Shestak
, p. 2171 - 2190 (2014/11/07)
A reaction of acetylacetone with equimolar amount of concentrated aqueous H2O2 in both organic solvents (ButOH, AcOH) and water at various temperatures gave the corresponding 3,5-dihydroxy-1,2- dioxolanes with different configuration of stereogenic centers. In the pres-ence of an excess of H2O2, 3,5-dihydroxy-1,2-dioxolanes were converted to a mixture of 5-hydroperoxy-3-hydroxy-1,2-dioxolanes and further to a mixture of dimeric 1,2-dioxolan-3-ylperoxides. All the peroxides formed exist in solutions as equilibrium mixtures with the starting reagents. A prolonged reflux of solutions of 3,5-dihydroxy-1,2-dioxolanes in ButOH in the presence of a large excess of H2O2 led to the skeletal rearrangements of the substrates to a mixture of propionic acid and hydroxyacetone, which underwent further oxidative transfor-mations. Unlike acetylacetone, 2-acetylcyclopentanone reacted with H2O2 in aqueous phase or in solutions in ButOH under thermodynamic or kinetic control with the formation of the corresponding 5-hydroperoxy-3-hydroxy- 1,2-dioxolanes, rather than 3,5-dihydroxy-1,2-di-oxolanes. Thermodynamically controlled process in solution in AcOH gave a mixture of all four possible hydroperoxyhydroxy-1,2-dioxolanes. These cyclic peroxides in solutions in ButOH or AcOH readily converted to a mixture of AcOH, glutaric, α-methyladipic, and α-hydroxy-α-methyladipic acids. An active α-hydroxylation of the substrate was observed upon reflux of a solution of 2-acetylcyclopentanone and H2O2 in AcOH.
Homobivalent ligands of the atypical antipsychotic clozapine: Design, synthesis, and pharmacological evaluation
McRobb, Fiona M.,Crosby, Ian T.,Yuriev, Elizabeth,Lane, J. Robert,Capuano, Ben
supporting information; experimental part, p. 1622 - 1634 (2012/04/17)
To date all typical and atypical antipsychotics target the dopamine D 2 receptor. Clozapine represents the best-characterized atypical antipsychotic, although it displays only moderate (submicromolar) affinity for the dopamine D2 receptor. Herein, we present the design, synthesis, and pharmacological evaluation of three series of homobivalent ligands of clozapine, differing in the length and nature of the spacer and the point of attachment to the pharmacophore. Attachment of the spacer at the N4′ position of clozapine yielded a series of homobivalent ligands that displayed spacer-length-dependent gains in affinity and activity for the dopamine D 2 receptor. The 16 and 18 atom spacer bivalent ligands were the highlight compounds, displaying marked low nanomolar receptor binding affinity (1.41 and 1.35 nM, respectively) and functional activity (23 and 44 nM), which correspond to significant gains in affinity (75- and 79-fold) and activity (9- and 5-fold) relative to the original pharmacophore, clozapine. As such these ligands represent useful tools with which to investigate dopamine receptor dimerization and the atypical nature of clozapine.
Thermal and photochemical oxidation of 2-acetylcyclopentanone with atmospheric oxygen
Novikov,Shestak
, p. 1099 - 1110 (2013/07/26)
The major products of thermal (acetone, CaCl2 excess, reflux) and photochemical (acetone or CCl4, room temperature) oxidation of 2-acetylcyclopentanone with atmospheric oxygen are 2-acetyl-2- hydroxycyclopentanone, 2-acetyl-2-hydroxy
METHOD FOR PRODUCING CARBOXYLIC ANHYDRIDE AND ARYLBORONIC ACID COMPOUND
-
Page/Page column 14, (2012/01/13)
When phthalic acid is heated in heptane under azeotropic reflux conditions in the presence of a catalytic amount of an arylboronic acid compound (such as 2,6-(diisopropylaminomethyl)phenylboronic acid or 2,6-bis(diisopropylaminomethyl)phenylboronic acid), phthalic anhydride is obtained in high yield.
