51936-06-2Relevant academic research and scientific papers
ENOL ETHER PROPERFUME
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Page/Page column 34, (2020/01/11)
The present invention relates to compounds of formula (I) as properfume compounds. In particular, the present invention relates to a method to release a compound being a ketone or aldehyde of formula (II), a formate ester of formula (III) and/or an alcoho
1,3-Dioxane as a scaffold for potent and selective 5-HT1AR agonist with in-vivo anxiolytic, anti-depressant and anti-nociceptive activity
Franchini, Silvia,Sorbi, Claudia,Linciano, Pasquale,Carnevale, Gianluca,Tait, Annalisa,Ronsisvalle, Simone,Buccioni, Michela,Del Bello, Fabio,Cilia, Antonio,Pirona, Lorenza,Denora, Nunzio,Iacobazzi, Rosa Maria,Brasili, Livio
, p. 310 - 325 (2019/05/21)
A series of compounds generated by ring expansion/opening and molecular elongation/simplification of the 1,3-dioxolane scaffold were prepared and tested for binding affinity at 5-HT1AR and α1 adrenoceptors. The compounds with greater affinity were selected for further functional studies. N-((2,2-diphenyl-1,3-dioxan-5-yl)methyl)-2-(2-methoxyphenoxy)ethan-1-ammonium hydrogen oxalate (12) emerged as highly potent full agonist at the 5-HT1AR (pKi 5-HT1A = 8.8; pD2 = 9.22, %Emax = 92). The pharmacokinetic data in rats showed that the orally administered 12 has a high biodistribution in the brain compartment. Thus, 12 was further investigated in-vivo, showing an anxiolytic and antidepressant effect. Moreover, in the formalin test, 12 was able to decrease the late response to the noxious stimulus, indicating a potential use in the treatment of chronic pain.
Substrate-Dependent Electrochemical Dimethoxylation of Olefins
Zhang, Sheng,Li, Lijun,Wu, Ping,Gong, Pengjuan,Liu, Rui,Xu, Kun
supporting information, p. 485 - 489 (2019/01/04)
A general and direct electrochemical dimethoxylation of olefins is reported, which enables a divergent route to different products depending on the structure of olefins. The present protocol features mild conditions and broad substrate scope (49 examples) obviating the usage of transtion-metals and external oxidants. More importantly, to rationalize the divergent route of the transformation, an ionic-like pathway involving carbocation intermediate is proposed and the diverse products is attributed to the different stability of carbocations. (Figure presented.).
FeCl3·6H2O-catalyzed mukaiyama-aldol type reactions of enolizable aldehydes and acetals
Rodríguez-Gimeno, Alejandra,Cuenca, Ana B.,Gil-Tomás, Jesús,Medio-Simón, Mercedes,Olmos, Andrea,Asensio, Gregorio
, p. 8263 - 8270 (2015/03/18)
Mukaiyama-aldol type reactions of acetals derived from enolizable aldehydes with FeCl3·6H2O, an eco-friendly, low-cost, and stable catalyst, lead to β-methoxycarbonyl compounds with nearly quantitative yields. The methodology is extended to the parent aldehydes as starting materials, leading to the corresponding aldols with lower yields, but efficiently. Different alkyl and aryl substituted acetals and aldehydes have been tested in the reaction with linear and cyclic silyl enol ethers. Reactions are carried out in an open air atmosphere, and additives are not required. Acetals can be considered activating groups of the carbonyl moiety rather than a protecting group in this type of FeCl3·6H2O-catalyzed condensation.
Epoxide ring-opening and Meinwald rearrangement reactions of epoxides catalyzed by mesoporous aluminosilicates
Robinson, Mathew W. C.,Davies, A. Matthew,Buckle, Richard,Mabbett, Ian,Taylor, Stuart H.,Graham, Andrew E.
experimental part, p. 2559 - 2564 (2009/10/30)
Mesoporous aluminosilicates efficiently catalyze the ring-opening of epoxides to produce β-alkoxyalcohols in high yields under extremely mild reaction conditions. These materials also catalyze the corresponding Meinwald rearrangement in non-nucleophilic solvents to give aldehydes which can be trapped in situ to provide the corresponding acetals in an efficient tandem process. The Royal Society of Chemistry 2009.
Construction of electrocatalytic electrodes bearing the triphenylamine nucleus covalently bound to carbon. A halogen dance in protonated aminotriphenylamines
Mayers, Brian T.,Fry, Albert J.
, p. 411 - 414 (2007/10/03)
The triarylamine nucleus has been attached to a carbon fiber electrode by diazotization of an aminotriphenylamine followed by electrochemical reduction. The resulting electrodes can electrocatalyze the oxidation of organic substrates. In acid, 4-amino-4′,4″-dibromotriphenylamine undergoes dismutation into a mixture of amines containing from 0 to 3 bromine atoms.
Use of delaminated zeolites (ITQ-2) and mesoporous molecular sieves in the production of fine chemicals: Preparation of dimethylacetals and tetrahydropyranylation of alcohols and phenols
Corma,Rodriguez,Climent,Iborra,Fornes
, p. 441 - 447 (2007/10/03)
The combination of zeolitic acidities, easy reactant accessibility, and fast desorption-diffusion of products are determinant issues for designing successful catalysts for acid-catalyzed reactions in the field of fine chemicals production. Protection of aldehydes by formation of the corresponding dimethyl acetals and of alcohols and phenols by formation of the corresponding tetrahydropyranyl ethers were performed using ITQ-2 zeolite as acid catalyst. Its catalytic activity for these reactions was compared with those obtained with MCM-22, Beta zeolites, and the mesoporous aluminosilicate MCM-41, all with similar Si/Al ratios. When the reactions involved bulky reactants, ITQ-2 showed, in all cases, the highest activity as a consequence of the combination of its delaminated structure and the presence of strong acid sites. The zeolitic nature of the acid sites present in the delaminated ITQ-2 zeolite made the acid sites more stable than those present in the short range amorphous MCM-41 molecular sieve, providing the former catalyst better activity and thermal regenerability. ITQ-2 and MCM-41 are active and selective catalysts for acetalization reactions involving reactants as large as diphenylacetaldehyde and cholesterol.
The photochemistry of 4-halobenzonitriles and 4-haloanisoles with 1,1-diphenyiethene in methanol. Homolytic cleavage versus electron-transfer pathways
Mangion, Dino,Arnold, Donald R.
, p. 1655 - 1670 (2007/10/03)
The photochemical reactivity of a series of 4-halobenzonitriles and 4-haloanisoles with 1,1-diphenylethene in a nucleophilic solvent (methanol) has been investigated. Analysis of the photochemical reactions involving the 4-halobenzonitriles revealed formation of alkene-methanol adducts, such as 1-methoxy-2,2-diphenylethane, 1-methoxy-2,2-diphenylethene, and 1,1-dimethoxy-2,2-diphenylethane, indicative of a photochemical electron-transfer mechanism. These products were not significant in the photochemical reactions involving the 4-haloanisoles. Both the 4-halobenzonitriles and the 4-haloanisoles produced an 'arene-alkene-methanol Markovnikov adduct, 1-aryl-2-methoxy-2,2-diphenylethane (aryl = 4-cyanophenyl or 4-methoxyphenyl). This compound was shown to undergo an acid-catalysed elimination to 1-aryl-2,2-diphenylethene under the reaction conditions, which subsequently underwent a 6π-electrocyclization to the 3-substituted(cyano or methoxy)-9-phenylphenanthrene. Possible mechanisms for the observed reactivity are discussed and evaluated.
Rearrangement of trans-stilbene into diphenylacetaldehyde acetals induced by direct anodic oxidation
Ogibin, Yu. N.,Ilovaisky, A. I.,Nikishin, G. I.
, p. 2089 - 2092 (2007/10/03)
Direct anodic oxidation of trans-stilbene in lower alcohols and in some other solvents in the presence of KF or Bu4NBF4 is accompanied by its electrooxidatve rearrangement into diphenylacetaldehyde acetals; a competing reaction yields 1,2-dialkoxy-1,2-diphenylethanes. - Keywords: trans-stilbene; electrooxidation; rearrangement.
