611-99-4Relevant articles and documents
Selective Oxidation of Alkylarenes to the Aromatic Ketones or Benzaldehydes with Water
Du, Jihong,Duan, Baogen,Liu, Kun,Liu, Renhua,Yu, Feifei,Yuan, Yongkun,Zhang, Chenyang,Zhang, Jin
supporting information, (2022/02/09)
Here a palladium-catalyzed oxidation method for converting alkylarenes into the aromatic ketones or benzaldehydes with water as the only oxygen donor is reported. This C-H bond oxidation functionalization does not require other oxidants and hydrogen accep
AN IMPROVED AND COMMERCIALLY VIABLE PROCESS FOR PREPARATION OF ARYL KETONES
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Paragraph 0086-0087, (2020/09/12)
The present disclosure provides a process for preparing an aryl ketone of Formula I, comprising reacting a substituted benzene of Formula II with a carboxylic acid of formula IIIa and/or a carboxylic anhydride of formula IIIb in presence of an alkyl sulfonic acid acting as catalyst cum solvent/contacting medium. I, II, IIIa, IIIb, wherein, R1, R2, R3 and R4 are as defined in the description.
A molybdenum based metallomicellar catalyst for controlled and chemoselective oxidation of activated alcohols in aqueous medium
Thiruvengetam, Prabaharan,Chakravarthy, Rajan Deepan,Chand, Dillip Kumar
, p. 123 - 133 (2019/07/19)
A surfactant based oxodiperoxo molybdenum complex, which could activate molecular oxygen, has been employed as a catalyst for controlled oxidation of benzylic alcohols to corresponding carbonyls. The oxidation reactions were carried out under aqueous environment, however, in the absence of any extraneous base or co-catalyst. Sensitive/oxidizable functional groups like cyano, sulfide, hydroxyl, aryl-hydroxyl, alkene (internal/terminal), alkyne (internal/terminal), and acetal were tolerated during the transformations. Such selectivity is attributed to the mild nature of the catalyst. The methodology could also be scaled-up for multi-gram synthesis and the protocol is likely to find practical use since it requires an inexpensive recyclable-catalyst and easily available oxidant (under green conditions). A plausible mechanism is proposed with the help of preliminary computational study.
A new generation of ferrociphenols leads to a great diversity of reactive metabolites, and exhibits remarkable antiproliferative properties
Wang, Yong,Dansette, Patrick M.,Pigeon, Pascal,Top, Siden,McGlinchey, Michael J.,Mansuy, Daniel,Jaouen, Gérard
, p. 70 - 78 (2018/01/02)
Organometallic compounds bearing the redox motif [ferrocenyl-ene-phenol] have very promising antiproliferative properties which have been further improved by incorporating pertinent substituents able to engender new mechanisms. Here we show that novel ferrociphenols bearing a hydroxypropyl chain exhibit strong antiproliferative effects, in most cases much better than those of cisplatin, tamoxifen, or of previously described ferrociphenols devoid of this terminal OH. This is illustrated, in the case of one of these compounds, by its IC50 values of 110 nM for MDA-MB-231 triple negative breast cancer cells and of 300 nM for cisplatin-resistant A2780cisR human ovarian cancer cells, and by its GI50 values lower than 100 nM towards a series of melanoma and renal cancer cell lines of the NCI-60 panel. Interestingly, oxidative metabolism of these hydroxypropyl-ferrociphenols yields two kinds of quinone methides (QMs) that readily react with various nucleophiles, such as glutathione, to give 1,6- and 1,8-adducts. Protonation of these quinone methides generates numerous reactive metabolites leading eventually to many rearrangement and cleavage products. This unprecedented and fully characterized metabolic profile involving a wide range of electrophilic metabolites that should react with cell macromolecules may be linked to the remarkable profile of antiproliferative activities of this new series. Indeed, the great diversity of unexpected reactive metabolites found upon oxidation will allow them to adapt to various situations present in the cancer cell. These data initiate a novel strategy for the rational design of anticancer molecules, thus opening the way to new organometallic potent anticancer drug candidates for the treatment of chemoresistant cancers.
Synthetic method for ultraviolet absorbent namely 4,4'-dihexyloxybenzophenone
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Paragraph 0021; 0026; 0031; 0036; 0041, (2017/09/13)
The invention discloses a synthetic method for an ultraviolet absorbent namely 4,4'-dihexyloxybenzophenone. The method comprises the following steps: with p-hydroxybenzoic acid as a starting material, carrying out acetylation to protect hydroxy; carrying out a Fredel-Crafts reaction of p-acetoxybenzoic acid and phenol under the catalysis of zinc chloride and phosphorus oxychloride so as to synthesize an intermediate namely phenyl p-hydroxybenzoate; then carrying out deacetylation to remove the protective group, and carrying out Fries rearrangement so as to prepare an intermediate namely 4,4-dihydroxybenzophenone; and forming a salt with 4,4-dihydroxybenzophenone and potassium carbonate, and carrying out a Williamson reaction of 1-bromohexane and the potassium salt of 4,4-dihydroxybenzophenone through catalysis of tetrabutylammonium bromide so as to synthesize the 4,4'-dihexyloxybenzophenone. The synthetic method provided by the invention has the advantages of mild reaction conditions, normal pressure, medium and low temperature, stable quality control, high raw material conversion rate, effective inhibition of side reactions, fewer three wastes, light pollution, and facilitation of protecting the environment and labor of a producer.
Organometallic Antitumor Compounds: Ferrocifens as Precursors to Quinone Methides
Wang, Yong,Pigeon, Pascal,Top, Siden,McGlinchey, Michael J.,Jaouen, Grard
, p. 10230 - 10233 (2015/09/01)
The synthesis and chemical oxidation profile of a new generation of ferrocifen derivatives with strong antiproliferative behavior in vitro is reported. In particular, the hydroxypropyl derivative HO(CH2)3C(Fc)=C(C6H4OH)2 (3 b) exhibited exceptional antiproliferative activity against the cancer cell lines HepG2 and MDA-MB-231 TNBC, with IC50 values of 0.07 and 0.11 μM, respectively. Chemical oxidation of 3 b yielded an unprecedented tetrahydrofuran-substituted quinone methide (QM) via internal cyclization of the hydroxyalkyl chain, whereas the corresponding alkyl analogue CH3CH2-C(Fc)=C(C6H4OH)2 merely formed a vinyl QM. The ferrocenyl group in 3 b plays a key role, not only as an intramolecular reversible redox "antenna", but also as a stabilized carbenium ion "modulator". The presence of the oxygen heterocycle in 3 b-QM enhances its stability and leads to a unique chemical oxidation profile, thus revealing crucial clues for deciphering its mechanism of action in vivo.
Stimuli-responsive blue fluorescent supramolecular polymers based on a pillar[5]arene tetramer
Song, Nan,Chen, Dai-Xiong,Qiu, Yu-Chen,Yang, Xiao-Yue,Xu, Bin,Tian, Wenjing,Yang, Ying-Wei
supporting information, p. 8231 - 8234 (2014/07/21)
A tetraphenylethene-bridged pillarene tetramer with aggregation-induced emission properties forms an A4/B2-type supramolecular polymer and a gel with a symmetric neutral guest linker, showing a remarkable fluorescence emission enhancement in solution and the solid state and a good responsiveness to temperature and solvent composition. This journal is the Partner Organisations 2014.
Pd/Cu-cocatalyzed aerobic oxidative carbonylative homocoupling of arylboronic acids and CO: A highly selective approach to diaryl ketones
Ren, Long,Jiao, Ning
supporting information, p. 2411 - 2414 (2014/10/15)
A highly selective Pd/Cu-cocatalyzed aerobic oxidative carbonylative homocoupling of arylboronic acids has been developed. This method employs a simple catalytic system, readily available boronic acids as the substrates, molecular oxygen as the oxidant, and 1 atm of CO/O2, which makes this method practical for further applications.
AIE (AIEE) and mechanofluorochromic performances of TPE-methoxylates: Effects of single molecular conformations
Qi, Qingkai,Liu, Yifei,Fang, Xiaofeng,Zhang, Yumo,Chen, Peng,Wang, Yi,Yang, Bing,Xu, Bin,Tian, Wenjing,Zhang, Sean Xiao-An
, p. 7996 - 8002 (2013/07/19)
Two methoxy-substituted tetraphenylethylene (TPE) derivatives, tetra(4-methoxyphenyl)ethylene (TMOE) and tetra(3,4-dimethoxyphenyl)ethylene (TDMOE), were synthesized by McMurry reaction in high yields. The nearly centrosymmetric and natural propeller shape of TMOE and TDMOE excluded intermolecular effects, such as H or J-aggregation and π-π stacking, on their AIE (AIEE) and mechanofluorochromic performance. The crystal structures of TMOE and TDMOE, and theoretical calculations proved that their emission colours are determined by single molecular conjugation. These molecules were used to investigate pure conformational effects on molecular emissions. The spectral properties of these molecules in five environments of crystal(s), THF solution, THF-water binary solution, solidified THF and amorphous states, were investigated. The crystalline to amorphous phase transition by grinding resulted in good mechanofluorochromic performances with high quantum yields and distinguishable emission change, which was further explored as anti-counterfeiting inks on banknotes.
Evaluation of polyhydroxybenzophenones as α-glucosidase inhibitors
Hu, Xuesen,Xiao, Yang,Wu, Jianlong,Ma, Lin
experimental part, p. 71 - 77 (2011/09/21)
This experiment was designed to synthesize 18 kinds of polyhydroxybenzophenones by using Friedel-Crafts reaction, and to measure the inhibitory activity on α-glucosidase with p-nitrophenyl-β-D- galactopyranoside (PNPG) as a substrate. Here, acarbose (IC50a= a1674.75aaμmolaL-1) was used as the reference inhibitor. The results demonstrated that most of the target compounds had remarkable inhibitory activities on α-glucosidase. Among all these compounds, 2,4,4′,6-butahydroxydiphenylketone (11) was found to be the most potent α-glucosidase inhibitor with an IC50 value of 10.62aaμmolaL-1. In addition, we found these compounds were competitive inhibitors through the kinetic analysis. The results suggested that such compounds might be utilized for the development of new candidates for diabetes treatment. A series of polyhydroxybenzophenones was synthesized and evaluated as α-glucosidase inhibitors. Compound 11 was found to be the most potent inhibitor. Copyright
