cas 32136-81-5, 1-(4-hydroxyphenyl)-2-methoxyethan-1-one

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Flavylium based dual photochromism: Addressing cis - trans isomerization and ring opening-closure by different light inputs
The multistate system of 4′,7-dihydroxy-3-methoxyflavylium is constituted by a multiequilibrium involving trans-chalcone, cis-chalcone, hemiketal, flavylium cation and quinoidal base. This system possesses two independently addressable inter-connected photochromic systems based on the cis - trans isomerization and ring opening-closure of the hemiketal.
Gago, Sandra,Basílio, Nuno,Moro, Artur J.,Pina, Fernando
p. 7349 - 7351
(2015)
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Removal of metoprolol by means of photo-oxidation processes
In this study, β-blocker metoprolol was degraded by photocatalysis and photo-Fenton catalyzed by doped TiO2. The effect of two main variables was elucidated, content and type of doping cation (Fe or Cu). The catalysts were synthesized by Evaporation-Induced Self-Assembly (EISA) method and their performance was compared with typical Degussa P25. All synthesized materials were found to be mesoporous with a specific surface in the range of 121–242 m2/g, they all exhibited anatase phase, and crystallites in the range of 6–10 nm. The use of X-ray photoelectron spectroscopy (XPS) allowed to establish not only the presence of the expected Ti4+ but also Ti3+ species. Cu2+ and Fe3+ species were also identified in the doped catalysts. It was found that the addition of Cu and Fe diminished the energy band gap of synthesized TiO2, from 3.20 eV to 2.58 and 2.64, respectively. The content of Cu is directly correlated with this effect. In photocatalysis, the doping of TiO2 did not have an effect of metoprolol degradation rate. This was improved, however, approximately 60% by the synthesized TiO2 compared to Degussa P25. On the other hand, the photo-Fenton-like process catalyzed by Cu-TiO2 exhibited the highest degradation (total removal) and mineralization extent (90%), being faster than the photocatalytic process and the UV-H2O2 system. Another difference between both methods, was the amount and type of intermediates generated. These were identified by LC-MS. Photo-Fenton catalyzed by Cu/TiO2 can be considered as an effective process with high oxidative power in the metoprolol degradation.
Avilés-García, Osmín,Brewer, Sharon,Donkor, Kingsley,Espino-Valencia, Jaime,Mendoza-Zepeda, Arisbeht,Natividad, Reyna,Romero, Rubi
(2021/07/07)

Synthesis method for preparing metoprolol intermediate
A synthesis method for preparing a metoprolol intermediate comprises the following steps: 1, dissolving phenol and chloroacetyl chloride in a dichloroethane solvent, adding aluminum trichloride as a catalyst, stirring for reaction to generate 4-chloracetyl phenol; 2, dissolving the 4-chloracetyl phenol generated by the reaction of the step 1 in methanol, adding methanol sodium, starting a stirrer for stirring for reaction to generate 4-(2'-methoxy acetyl) phenol; 3, adding the 4-(2'-methoxy acetyl) phenol generated by the reaction of the step 2 into a reactor, adding a catalyst, adding a reductant, starting stirring, and heating for reaction to generate intermediate 4-(2 '-methoxy ethyl) phenol. The advantages are as follows: the method for preparation of the 4-(2 '-methoxy ethyl) phenol is simple in operation, mild in conditions, environmental friendly, low in cost, and is suitable for industrial production, Raney nickel can be reused, the reaction yield reaches 86%, and the purity reaches 98% or above.
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(2017/12/27)

Direct Synthesis of α-Alkoxy Ketones by Oxidative C–O Bond Formation
A convenient method to prepare α-alkoxy ketones has been developed by oxidative coupling of aryl methyl ketones and alcohols. With aqueous tert-butyl hydroperoxide (6.0 equiv.) as the oxidant, tetrabutylammonium iodide (20 mol-%) as the catalyst, and TsNHNH2(1.0 equiv.) as the additive, ketones underwent direct alkoxylation to give α-methoxy or α-ethoxy ketones in moderate to good yields.
Yu, Hui,Xu, Yilan,Fang, Yan,Dong, Rui
p. 5257 - 5262
(2016/11/13)

Synthesis and cardiovascular activity of metoprolol analogues
The synthesis of four novel analogues of metoprolol, a well-known β1-blocker used to reduce arterial blood pressure, is described. The preparation of (2S,2′S)-7, (2R,2′S)-7, (2R,2′R)-8, and (2S,2′R)-8 was based on the reaction of racemic 2-[4-(2′- methoxyethyl)-phenoxymethyl]-oxirane (4) with (R)- or (S)-2-amino-1-butanol. Salient characteristics of analogues 7 and 8 relative to metoprolol are the incorporation of an additional stereogenic center, as well as a methyl group and a hydroxyl function on the nitrogen-containing chain. These novel derivatives present significant hypotensive and bradycardiac activity, although no blocking action toward β1 and β2 adrenergic receptor.
Melgar-Fernandez, Roberto,Demare, Patricia,Hong, Enrique,Rosas, Miguel Angel,Escalante, Jaime,Munoz-Muniz, Omar,Juaristi, Eusebio,Regla, Ignacio
p. 191 - 194
(2007/10/03)

DIHALO-ALLYLOXY-PHENOL DERIVATIVES HAVING PESTICIDAL ACTIVITY
Compounds of formula (I), wherein A1 and A2 are each independently of the other a bond or a C1-C6alkylene bridge; A3 is a C1-C6alkylene bridge; X1 and X2 are each independently of the other fluorine, chlorine or bromine; Y is O, NR7, S, SO or SO2; R1, R2 and R3 are each independently of the others, for example, H, halogen, OH, SH, CN, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylcarbonyl or C2-C6alkenyl; Q is O, NR5, S, SO or SO2; W is, for example, O, NR5 or SO; T is for example, a bond, O or NR5; D is CH or N; R4 is, for example, H, halogen, OH, SH, CN or nitro; R5 and R7 are, for example, H, C1-C6alkyl or C1-C3haloalkyl; k is 1, 2, 3 or 4; m is 1 or 2; R10 is a radical which contains O, N or S; R11 is, for example, H, C1-C12alkyl or a radical which contains from one to three hetero atoms selected from O, N and S; or R11 together with R12 is a bond; R12 is, for example, H, C1-C6alkyl, halo-C1-C6alkyl or C1-C6alkoxy-C1-C6-alkyl; and, where applicable, their possible E/Z isomers, E/Z isomeric mixtures and/or tautomers, in each case in free from or in salt form, a process for the preparation of those compounds and their use, pesticidal compositions in which the active ingredient has been selected from those compounds or an agrochemically acceptable salt thereof; a process for the preparation of those compositions and their use, plant propagation material treated with those compositions, and a method of controlling pests.
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Page 38

(2010/02/07)

PESTICIDALLY ACTIVE KETONE AND OXIME DERIVATIVES
Compounds of formula (I), wherein A0, A1, and A2 are each independently of the others a bond or a Cl-C6alkylene bridge; A3 is a Cl-C6alkylene bridge which is unsubstituted or substituted by from one to six identical or different substituents selected from halogen and C3-C8cycloalkyl; Y is, for example, 0, S, SO or S02; M is 0 or NOR6, X1, and X2 are each independently of the other fluorine, chlorine or bromine; R1, R2and R3 are, for example, H, halogen, OH, SH, CN, nitro, C1-C6alkyl, Cl-C6haloalkyl, Cl-C6alkylcarbonyl, C2-C6alkenyl, C2-C6haloalkenyl or C2-C6alkynyl; Q is, for example, O, S, SO or SO2; W is, for example, 0, S, SO, SO2, -C(=O)-O- or -0-C(=O)-; T is, for example, a bond, 0, S, SO, S02, -C(=O)-O-or -0-C(=O)-; D is CH or N; R4 is, for example, H, halogen, OH, SH, CN, nitro, Cl-C6alkyl or C1-C6haloalkyl; R5is, for example, Cl-Cl2alkyl, C3-C8cycloalkyl or -N(R7)2; R7 is H, C1-C6alkyl, Cl-C3haloalkyl, Cl-C6alkylcarbonyl, Cl-C3haloalkylcarbonyl, Cl-C6alkoxycarbonyl, C3-C8Cycloalkyl, C3-C8 cycloalkylcarbonyl or formyl; k is 0, 1, 2, 3 or 4; m is 1 or 2; and q is 0, 1 or 2; and, where applicable, their possible E/Z isomers, E/Z isomeric mixtures and/or tautomers, in each case in free form or in salt form, a process for the preparation of those compounds and their use, pesticidal compositions in which the active ingredient has been selected from those compounds and agrochemically acceptable salts thereof, and a process for the preparation of those compositions and their use, to plant propagation material treated with those compositions, and a method of controlling pests.
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Page 37

(2008/06/13)

Syntheses of bryophyte constituents. 8. Sphagnum acid and its degradation products
For Sphagnum acid (1) and its enzymatic degradation product 5-hydroxy-4-(4-hydroxyphenyl)-5H-furan-2-on (2) efficient syntheses on preparative scale were developed. For the (4-hydroxyphenyl)butenolide 2 some characteristic chemical transformations are observed in acidic and basic medium. Johann Ambrosius Barth 1996.
Eicher,Wobido,Speicher
p. 706 - 710
(2007/10/03)

145. Synthesis of 3-Methoxy- and 3-(β-D-Glucopyranosyloxy)flavylium Ions. Influence of the Flavylium Substitution Pattern on the Reactivity of Anthocyanins in Aqueous Solution
The synthesis of 3-glycosyloxylated flavylium ions (anthocyanins), in particular of callistephin (4), a natural anthocyanin, is described.The structural transformations in aqueous solution and molecular complexation with chlorogenic acid (7) and caffeine (8) of the synthesized pigments 3 and 4 are investigated and compared to those of the corresponding 3-methoxyflavylium ions 1 and 2 and to those of oenin (5) and malvin (6), two very common natural anthocyanins.The results are discussed in terms of the role played by the glycosyloxy residues in the chemical properties of anthocyanins.Anthocyanin molecular complexation (copigmentation) is quantitatively investigated by UV/VIS spectroscopy and 1H-NMR.In particular, the UV/VIS spectroscopic data are interpreted using a general theoretical treatment, which, e.g., allows to demonstrate the formation of molecular complexes between the colourless forms of an anthocyanin and 8.
Dangles, Olivier,Elhajji, Hakima
p. 1595 - 1610
(2007/10/02)

Method for producing 4-(2'-methoxyethyl)phenol
The invention provides a method for producing 4-(2'-methoxyethyl)phenol by brominating 4-hydroxyacetophenone to produce alpha-bromo-5-hydroxyacetophenone, and then causing a methoxide-bromide exchange to thereby produce alpha-methoxy-4-hydroxyacetophenone; and then conducting a single step reduction of alpha-methoxy-4-hydroxyacetophenone with at least two equivalents of hydrogen per equivalent of alpha-methoxy-4-hydroxyacetophenone in the presence of a hydrogenation catalyst to thereby directly produce 4-(2'-methoxyethyl)phenol.
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(2008/06/13)

A New Route to (+/-) Metoprolol
Synthesis of 4-(2-methoxyethyl)phenol (5) from phenol is described.The derived aryloxyallyl ether (6) is converted into (+/-)-metoprolol (10) by involving dihydroxylation reaction with OsO4 and NMO.
Gurjar, M.K.,Joshi, Shreerang V,Sastry, B.S.,Rao, A V Rama
p. 3489 - 3496
(2007/10/02)

Chemical Aspects of Metoprolol Metabolism. Asymmetric Synthesis and Absolute Configuration of the 3--1-(isopropylamino)-2-propanols, the Diastereomeric Benzylic Hydroxylation Metabolites
Asymmetric synthesis of 3--1-(isopropylamino)-2-propanol (2), the benzylic hydroxylation metabolite of metoprolol (1), is described, and the absolute configurations of the diastereomers were assigned.Ketone 3, prepared in a multistep synthesis, was reduced with a complex of (2S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol(9) and borane, yielding 2, with a ratio of 82:18 for the diastereomers.The absolute configurations 1'S,2S and 1'S2R were assigned for the diastereomers formed in excess on the basis of reductions on closely related alkyl phenyl ketones and the circular dichroism spectrum.Derivatization of the 1'-hydroxyl group of oxazolidinone 10 with a chiral Mosher acid chloride and the use of an HPLC procedure to resolve the resulting esters enabled us to determine the metabolic product stereoselectively for 2.In the presence of the rat liver microsomal fraction, the benzylic hydroxylation of 1 was highly product stereoselective favoring 1'R stereochemistry at the new asymmetric center in racemic 1 and in both enantiomers of 1.Determination of the stereochemistry of 2 will facilitate study of this polymorphically controlled metabolic process.
Shetty, H. Umesha,Nelson, Wendel L.
p. 55 - 59
(2007/10/02)