4942-47-6Relevant articles and documents
Synthesis and Properties of 1,3-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: VII. Synthesis and Properties 1-[(Adamantan-1-yl)methyl]-3-(fluoro, chlorophenyl) Ureas
Danilov,D’yachenko,Kuznetsov,Burmistrov,Butov
, p. 143 - 150 (2021/04/02)
Abstract: A series of 1,3-disubstituted ureas containing a lipophilic adamantane moiety tethered to the ureido group by a methylene bridge were synthesized by the reaction of 1-(isocyanatomethyl)adamantane with monohalo- and dihaloanilines in yields of up to 92%. The synthesized ureas are target oriented inhibitors of human soluble epoxide hydrolase (sEH).
Method for preparing carboxylic acid by one-pot method
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Paragraph 0081-0085, (2021/01/29)
The invention discloses a method for preparing carboxylic acid by a one-pot method, which comprises the steps of carrying out a Corey-Fuchs process on 1,1-dibromo olefin under the action of n-butyllithium, reacting with isopropanol pinacol borate, quenching with hydrogen chloride, oxidizing with an oxidant, separating and purifying to obtain carboxylic acid. The method disclosed by the invention is a one-pot preparation method, is simple and convenient to operate, does not need to use metal catalysis, uses cheap and easily available reagents for reaction, is green and environment-friendly, hasmild reaction conditions and wide substrate applicability, and provides a new way for rapidly preparing a series of carboxylic acids containing different functional groups.
Peculiar Features of the Willgerodt–Kindler Reaction of 1-Adamantylpropan-2-one and Its Derivatives
Novakov,Orlinson,Savel’ev,Potaenkova,Vostrikova,Tarakanov,Nakhod
, p. 2762 - 2765 (2018/02/21)
The Willgerodt–Kindler reaction of 1-(1-adamantyl)propan-2-one and its derivatives was studied by gas chromatography–mass spectrometry. The reaction time was found to be 3–4 times longer than in the case of alkyl aryl ketones due to considerable steric hindrances in the molecules of adamantyl ketones. The use of diglyme as solvent and sodium butyl xanthate as catalyst significantly shortened the reaction time and improved the yield to 92%.
Hydrolysis and retro-aldol cleavage of ethyl threo-2-(1-adamantyl)-3- hydroxybutyrate: Competing reactions
Ganguly, Bishwajit,Kesharwani, Manoj K.,Matkovic, Marija,Basaric, Nikola,Singh, Ajeet,Mlinaric-Majerski, Kata
, p. 578 - 587 (2013/01/11)
The hydrolysis of ethyl threo-2-(1-adamantyl)-3-hydroxybutyrate (1) and the parent ester ethyl 3-hydroxybutyrate (4) has been studied experimentally and computationally. In the hydrolysis of threo-ester 1 with 2M NaOH, predominantly retro-aldol product was observed, whereas the hydrolyzed product was present in a minor amount. When the reaction is carried out under the same conditions with the parent ester ethyl 3-hydroxybutyrate (4), hydrolyzed product is exclusively observed. The competitive pathways, namely hydrolysis and the retro-aldol reaction for 1 and 4 were investigated using DFT calculations in the both gas and solvent phase. The calculated results in the solvent phase at B3LYP/6-31+G* level revealed that the formation of retro-aldol products is kinetically preferred over the hydrolysis of threo-ester 1 in the presence of a base. However, the parent ester 4 showed that the retro-aldol process is less favored than the hydrolysis process under similar conditions. The steric effect imposed by the bulky adamantyl group to enhance the activation barriers for the hydrolysis of the ethyl threo-2-(1-adamantyl)-3-hydroxybutyrate (1) was further supported by the calculations performed with tert-butyl group at the α-carbon atom of ethyl 3-hydroxybutyrate (7).
2-Hydroxy-1,2,2-triphenylethanone as an efficient photolabile protecting group for carboxylic acids
Ashraf, M. Arfan,Russell, Alexander G.,Wharton, Christopher W.,Snaith, John S.
, p. 586 - 593 (2007/10/03)
The synthesis is reported of 2-hydroxy-1,2,2-triphenylethanone esters of carboxylic acids by the reaction between 2-chloro-1,2,2-triphenylethanone and a carboxylic acid in the presence of silver carbonate and silver tetrafluoroborate. Photolysis of the esters occurs rapidly on irradiation with a medium-pressure mercury lamp through quartz or Pyrex to return the carboxylic acid. The side product of the photolysis is benzo[b]phenanthro[9,10-d]furan, formed through a tandem process involving initial generation of 2,3-diphenylbenzofuran, photochemical cyclisation and re-aromatisation by aerial oxidation.
The Invention of Radical Reactions. XXXIII Homologation Reactions of Carboxylic Acids by Radical Chain Chemistry
Barton, Derek H. R.,Chern, Ching-Yuh,Jaszberenyi, Joseph Cs.
, p. 407 - 426 (2007/10/02)
Various carbon radicals can be generated from carboxylic acids via the corresponding Barton esters.These radicals can be used for the synthesis of longer chain homologues of the original acids.
Scope and Mechanism of Deprotection of Carboxylic Esters by Bis(tributyltin) Oxide
Salomon, Claudio J.,Mata, Ernesto G.,Mascaretti, Oreste A.
, p. 7259 - 7266 (2007/10/02)
Methyl and ethyl esters of aliphatic and aromatic carboxylic acids as well as benzyl carboxylates, thiol esters and double esters such as (pivaloyloxy)methyl carboxylates have been successfully cleaved with bis(tributyltin) oxide to give the free carboxylic acids in good yields.The reaction is carried out in aprotic solvents under essentially neutral conditions and thus this method can serve as an ideal procedure for the cleavages of esters with other functional groups and/or protecting groups acid and/or base sensitive.We demonstrated that the reaction displays a high level of chemoselectivity between methyl and ethyl esters versus tert-butyl esters and γ-lactones.Bis(tributyltin) oxide is also a highly efficient reagent for the cleavage of acetates of primary and secondary alcohols and phenols.The limitations we found in the use of this reagent include the lack of cleavage of esters sterically hindered around the carboxyl carbon and the carbinol group (i.e., esters of tertiary alcohols) and in carboxylic esters that contain a fluoroalkyl substituent.A resonable mechanistic explanation is discussed to account for the reaction pathway of the acyloxygen cleavage of (-)-(1R)-menthyl acetate.
SYNTHESIS OF 2,2'-(ADAMANTYLENE-1,3)-DIETHANOIC ACIDS
Butenko, L. N.,Novakov, I. A.,Radchenko, S. S.,Kuznechikov, O. A.,Oglodina, T. Yu.,et al.
, p. 1244 - 1246 (2007/10/02)
Via direct oxidative addition of 1,1-dichloroethylene to adamantane or 1,3-dimethyladamantane one obtains diethanoic acids of the adamantane series, which are useful in themselves or for preparation of other functional derivatives.Optimal reaction conditions were found by mathematical modeling.Keywords: synthesis, adamantane, dimethyladamantane, 1,1-dichloroethylene, 1,3-bis(carboxymethyl)adamantane, 1,3-bis(carboxymethyl)-5,7-dimethyladamantane, mathematical planning.
