19973-76-3Relevant articles and documents
Solvent- and Wavelength-Dependent Photolysis of Estrone
Adriano, Natalie,Ahearn, Ceilidh,Black, Cory,Cracchiolo, Michael,Ghere, Daniel,Hare, Patrick M.,Nu?ez, Alexandra,Olivan, Lars,Patel, Raj,Saner, Stephanie,Smith, Krista R.,Watkins, Barbie
, (2021/11/08)
The direct photolysis of estrone in solvents ranging from water to cyclohexane is reported. The photodegradation is dominated by lumiestrone, an epimer of estrone resulting from the inversion of the methyl group at carbon 13, regardless of solvent and pho
Photochemical Behavior of Some Estrone Aryl and Methyl Sulfonates in Solution: Preparative and Mechanistic Studies
Quindt, Matías I.,Gola, Gabriel F.,Ramirez, Javier A.,Bonesi, Sergio M.
, p. 8 - 21 (2020/06/03)
Direct irradiation of estrone aryl and methyl sulfonates in different organic solvents under nitrogen atmosphere was investigated under steady-state conditions. The estrone derivatives reacted efficiently through the photo-Fries rearrangement reaction involving [1;3]-sulfonyl migration providing the ortho-sulfonyl estrone derivatives and estrone as the photoproducts. In addition, estrone and 2-arylsulfonyl estrone derivatives were epimerized involving a Norrish Type-I reaction. Chemical quenching and photosensitization experiments on the photoreaction have been also carried out to establish the photoreactive excited state. Likewise, the solvent effect and the nature of the sulfonyl group on the photoreactions have been also studied.
Pd-catalyzed Suzuki–Miyaura couplings and evaluation of 13α-estrone derivatives as potential anticancer agents
Ali, Hazhmat,Horváth, Gergely,Jójárt, Rebeka,Kele, Zoltán,Mernyák, Erzsébet,Zupkó, István
, (2020/10/02)
13α-Estrones are of great value owing to their potent multiple bioactivity, including anticancer activity. 3-OH or 3-OBn derivatives of 2- or 4-[(subst.) phenyl]-13α-estrone as potential antiproliferative agents have been synthesized via facile, microwave
Photo-Fries Rearrangement of Some 3-Acylestrones in Homogeneous Media: Preparative and Mechanistic Studies
Quindt, Matías I.,Gola, Gabriel F.,Ramirez, Javier A.,Bonesi, Sergio M.
, p. 7051 - 7065 (2019/06/18)
Irradiation of a series of 3-acylestrones under a nitrogen atmosphere in cyclohexane, acetonitrile (MeCN), and methanol (MeOH) was investigated under steady-state conditions. The molecules underwent the photo-Fries rearrangement, with concomitant homolytic fragmentation of the ester group and [1;3]-acyl migration. This pathway afforded the ortho-acyl estrone derivatives, the main photoproducts, together with estrone. During the irradiation of 3-benzoyl estrone, epimerization of estrone through the Norrish type I reaction occurred, providing lumiestrone as the photoproduct. This photoreaction involves the fragmentation of the C-α at the carbonyl group (C-17) of the steroid. On the other hand, epimerization of ortho-regioisomer 2-acetyl estrone occurred during the irradiation of 3-acetyl estrone. Photosensitization with acetone and chemical quenching with N,N,N,N-tetramethyldiazetinedioxide of the photo-Fries reaction confirmed that the photoreaction took place from the singlet excited state while the Norrish type I reaction proceeds efficiently from the triplet excited state. Solvent effects, as well as the nature of the acyl group on the photoreactions, were also studied.
HYDROXYLATION DE L'ESTRONE ET DE SON ACETATE PAR LE PEROXYDE D'HYDROGENE EN MILIEU SUPERACIDE
Berrier, C.,Jacquesy, J. C.,Jouannetaud, M. P.
, p. 5135 - 5142 (2007/10/02)
Estrone 1a and its acetate 1b react with hydrogen peroxide in SbF5-HF to give hydroxylated compounds.The formation of the dienone 2 can be accounted for by reaction of the electrophile H3O2+ on the neutral substrate, whereas formation of compound 3b implies electrophilic attack on the protonated ester 1b.Higher acidity favours rearrangement of the resulting ion 9 to yield, through a spiro intermediate, the ester 4b.Under the reaction conditions esters 3b and 4b are slowly converted into the corresponding phenols 3a and 4a.
