120-14-9Relevant articles and documents
Aromatic amide derivatives of 5,6-dimethoxy-2,3-dihydro-1H-inden(-1-yl)acetic acid as anti-inflammatory agents free of ulcerogenic liability
Sharma, Meenakshi,Ray
, p. 6790 - 6796 (2007)
Amide derivatives of 5,6-dimethoxy-2,3-dihydro-1H-inden(-1-yl)acetic acid were synthesized and evaluated for their anti-inflammatory and analgesic activity. Few selected compounds were also screened for their antipyretic, anti-arthritic, and ulcerogenic potential. Most of the compounds exhibited good activity profile and were free of gastrointestinal toxicity of common NSAIDs. However these compounds failed to decrease secondary lesions of adjuvant induced arthritis and also did not inhibit TNF-α in lipopolysaccharide induced pyresis.
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Stermitz et al.
, p. 1136,1139 (1968)
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Co-Oxidative Transformation of Piperine to Piperonal and 3,4-Methylenedioxycinnamaldehyde by a Lipoxygenase from Pleurotus sapidus
Krahe, Nina-Katharina,Berger, Ralf G.,Kahlert, Lukas,Ersoy, Franziska
, p. 2857 - 2861 (2021)
The valuable aroma compound piperonal with its vanilla-like olfactory properties is of high interest for the fragrance and flavor industry. A lipoxygenase (LOXPsa1) of the basidiomycete Pleurotus sapidus was identified to convert piperine, the abundant pungent principle of black pepper (Piper nigrum), to piperonal and a second volatile product, 3,4-methylenedioxycinnamaldehyde, with a vanilla-like odor through an alkene cleavage. The reaction principle was co-oxidation, as proven by its dependence on the presence of linoleic or α-linolenic acid, common substrates of lipoxygenases. Optimization of the reaction conditions (substrate concentrations, reaction temperature and time) led to a 24-fold and 15-fold increase of the piperonal and 3,4-methylenedioxycinnamaldehyde concentration using the recombinant enzyme. Monokaryotic strains showed different concentrations of and ratios between the two reaction products.
Benzyltriphenylphosphonium peroxymonosulfate: As a novel and efficient reagent for oxidation of alcohols under solvent-free conditions
Hajipour, Abdol Reza,Mallakpour, Shadpour E.,Adibi, Hadi
, p. 460 - 461 (2000)
This paper describes the oxidation of alcohols under solvent-free conditions using benzyltriphenylphosphonium peroxymonosulfate, which has been prepared by mixing an aqueous solution of benzyltriphenylphosphonium chloride with oxone at room temperature. This reagent is stable white powder, which may be stored for months without loss of its activity. This compound is readily soluble in organic solvents such as acetonitrile, chloroform, and dichloromethane and slightly soluble in carbon tetrachloride, ether, and hexane.
Flavanols, as plant growth inhibitor from roots of peach, Prunus persica Batsh. cv. 'Hakuto'
Ohigashi,Minami,Fukui,et al.
, p. 2555 - 2561 (1982)
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Oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers and ethylene acetals with benzyltriphenylphosphonium peroxomonosulfate in the presence of bismuth chloride under non-aqueous conditions
Hajipour,Mallakpour,Mohammadpoor-Baltork,Adibi
, p. 155 - 163 (2000)
Benzyltriphenylphosphonium peroxomonosulfate (BnPh3P+HSO5-) (1) is used as a new reagent for oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers and ethylene acetals to afford carbonyl compounds in refluxing acetonitrile in the presence of bismuth chloride.
Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis
Mu?kinja, Jovana,Burmud?ija, Adrijana,Ratkovi?, Zoran,Rankovi?, Branislav,Kosani?, Marijana,Bogdanovi?, Goran A.,Novakovi?, Sla?ana B.
, p. 1744 - 1753 (2016)
O-alkylated vanillin derivatives 2a–f and acetylferrocene react under Claisen–Schmidt conditions, resulting in good-to-high yields of the corresponding ferrocene chalcones 3a–f. None of the resultant compounds 3b–f has been previously described in the literature. All synthesized compounds were characterized by spectral and physical data, whereas two of them, 1-ferrocenyl-3-(4-ethoxy-3-methoxyphenyl)-prop-2-en-1-one (3b) and 1-ferrocenyl-3-(4-buthoxy-3-methoxy-phenyl)-prop-2-en-1-one (3e), were crystalline substances, suitable for single-crystal X-ray analysis, which confirmed undoubtedly their structures. Chalcones 3a–f were tested for their biological activity and demonstrated relatively good in vitro antimicrobial activity towards different strains of bacteria and fungi. The best antibacterial activity is expressed by compounds 3b and 3c, while compound 3d shows the best antifungal activity.
Nickel-catalyzed Ullmann-type coupling reaction to prepare tetra-ortho-substituted biaryls
Hong,Hoen,Zhang,Lin
, p. 1527 - 1530 (2001)
A nickel-catalyzed Ullmann-type reaction on the coupling of bis-ortho-substituted arylhalides to prepare tetra-ortho-biaryls was brought about in moderate to high yields. Bu4NI might function as an efficient bridging ligand to accelerate the formation of dinickel-center intermediate, which subsequently eliminates to desired coupling product.
An efficient and selective oxidation of benzylic alcohols to the corresponding carbonyl compounds under solvent-free conditions
Hajipour, Abdol Reza,Mallakpour, Shadpour E.,Mohammadpoor-Baltork, Iraj,Khoee, Sepideh
, p. 120 - 121 (2000)
1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octanedichromate is a useful reagent for selective oxidation of benzylicalcohols and α-hydroxy ketones to the corresponding carbonyl compounds. The reaction was carried out under solvent-free conditions without or in the presence of a catalytic amount of aluminum chloride.
Organocatalytic Chemoselective Primary Alcohol Oxidation and Subsequent Cleavage of Lignin Model Compounds and Lignin
Dabral, Saumya,Hernández, José G.,Kamer, Paul C. J.,Bolm, Carsten
, p. 2707 - 2713 (2017)
A one-pot two-step degradation of lignin β-O-4 model compounds initiated by preferred oxidation of the primary over the secondary hydroxyl groups with a TEMPO/DAIB system has been developed [TEMPO=2,2,6,6-tetramethylpiperidine-N-oxyl, DAIB=(diacetoxy)iodobenzene]. The oxidised products are then cleaved by proline-catalysed retro-aldol reactions. This degradation methodology produces simple aromatics in good yields from lignin model compounds at room temperature with an extension to organosolv beech-wood lignin (L1) resulting in known cleavage products.
Factors Controlling the Reactivity of a Ligninase Model Based on the Association of Potassium Monopersulfate to Manganese and Iron Porphyrin Complexes
Labat, Gilles,Meunier, Bernard
, p. 5008 - 5011 (1989)
An efficient ligninase model based on the association of potassium monopersulfate to iron and manganese porphyrin in solution or immobilized onto an ion-exchange resin is reported.High catalytic conversion of veratryl alcohol or 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol, a useful model molecule for checking the ability of cleaving Cα-Cβ bonds of arylglycerol-β-aryl ether linkages existing in lignin itself, is obtained at room temperature in a single-phase solution (buffered water/acetonitrile, 75/25, v/v) at pH 2-3 for iron porphyrin or at pH 4.5-6.0 for manganese porphyrin.The porphyrin ligand used in the present study is the meso-tetrakis(p-sulfonatophenyl)porphyrin (TPPS).Catalytic activities can be as high as eight cycles per second.
Ultrasound in Oxochromium(VI)-Amine-Mediated Oxidations-Modifications of the Corey-Suggs Oxidation for the Facile Conversion of Alcohols to Carbonyl Compounds
Adams, Laura L.,Luzzio, Frederick A.
, p. 5387 - 5390 (1989)
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Copper-Mediated Conversion of Complex Ethers to Esters: Enabling Biopolymer Depolymerisation under Mild Conditions
Xiao, Ganyuan,Montgomery, James R. D.,Lancefield, Christopher S.,Panovic, Isabella,Westwood, Nicholas J.
, p. 12397 - 12402 (2020)
Selective processing of the β-O-4 unit in lignin is essential for the efficient depolymerisation of this biopolymer and therefore its successful integration into a biorefinery set-up. An approach is described in which this unit is modified to incorporate a carboxylic ester with the goal of enabling the use of mild depolymerisation conditions. Inspired by preliminary results using a Cu/TEMPO/O2 system, a protocol was developed that gave the desired β-O-4-containing ester in high yield using certain dimeric model compounds. The optimised reaction conditions were then applied to an oligomeric lignin model system. Extensive 2D NMR analysis demonstrated that analogous chemistry could be achieved with the oligomeric substrate. Mild depolymerisation of the ester-containing oligomer delivered the expected aryl acid monomer.
Regeneration of aldehydes from bisulfite addition products in the solid state using montmorillonite KSF clay under microwave irradiation
Mitra, Alok Kumar,De, Aparna,Karchaudhuri, Nilay
, p. 560 - 561 (1999)
Microwave irradiation of bisulfite addition products with montmorillonite KSF clay under solvent-free conditions provides a fast, efficient and simple method for regeneration of aldehydes in excellent yields.
CeCl3·7H2O-promoted highly chemoselective hydrolysis of 1,3-oxathio- and dithioacetals
Yadav,Reddy,Raghavendra,Satyanarayana
, p. 4679 - 4681 (2002)
A highly selective hydrolysis of the 1,3-oxathio- and 1,3-dithioacetals has been achieved in high yields using CeCl3·7H2O-NaI in acetonitrile at reflux temperature under neutral conditions. This method is mild and compatible with a wide range of functional groups such as TBDPS, THP, PMB, MOM, allyl, propargyl, prenyl, benzyl ethers, carbamates and acetate, etc., present in the substrate.
Bioinspired aerobic oxidation of alcohols with a bifunctional ligand based on bipyridine and TEMPO
Wang, Lianyue,Bie, Zhixing,Shang, Sensen,Lv, Ying,Li, Guosong,Niu, Jingyang,Gao, Shuang
, p. 35008 - 35013 (2016)
A novel bioinspired bifunctional ligand incorporating metal-binding site and stable free radical has been synthesized. The catalytic system obtained from the bifunctional ligand with copper(i) iodide in the presence of N-methylimidazole is highly efficient for the oxidation of a broad range of primary benzylic, allylic, alkynyl, aliphatic alcohols and secondary benzylic alcohols to the corresponding aldehydes and ketones in good to excellent yields. The catalyst system exhibits broad functional-group compatibility. The reaction is carried out in acetonitrile as solvent under air balloon at room temperature. The catalyst system features excellent activity for primary aliphatic alcohol oxidation and a high chemoselective oxidation of primary alcohols over the secondary alcohols. This oxidation process is readily amenable to larger-scale application. The interaction of the different components in the reaction mixtures was studied by UV-visible spectroscopy. The data indicated that Cu(i) existed throughout the reaction. A plausible mechanism of the catalytic cycle is proposed.
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Beckett,Wright
, (1876)
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Aromatic Hydroxylation. Hydroxybenzaldehydes from Bromobenzaldehydes via Reaction of in Situ Generated, Lithiated α-Morpholinobenzyl Alkoxides with Nitrobenzene
Sinhababu, Achintya K.,Borchardt, Ronald T.
, p. 1941 - 1944 (1983)
A general method for the one-step conversion of bromobenzaldehydes to the corresponding hydroxybenzaldehydes has been developed.The method involves in situ protection of the aldehyde function of the bromobenzaldehyde as its lithium morpholinoalkoxide, followed by lithium-bromine exchange, reaction with nitrobenzene at -75 deg C, and a subsequent acidic workup.The method has been applied to the synthesis of 4,5-dimethoxy-3-hydroxy- (1a), 3,5-dimethoxy-2-hydroxy- (2a), 3,5-bis(benzyloxy)-2-hydroxy- (2b), 3,4-dimethoxy-2-hydroxy- (14), 3-hydroxy-4,5-(methylenedioxy)- (16), and 4,5-dimethoxy-2-hydroxybenzaldehydes (18) from the bromobenzaldehydes 4, 12a, 12b, 13, 15, and 17, respectively.
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Bhagwat,Moore,Pyman
, p. 443 (1931)
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Solid-phase oxidative halodecarboxylation of β-arylacrylic acids with the ceric ammonium nitrate-alkali halide system
Nikishin,Sokova,Makhaev,Kapustina
, p. 118 - 123 (2008)
The solid-phase oxidation of cinnamic, 4-methoxy- and 3,4-dimethoxycinnamic acids with Ce(NH4)2(NO3)6-MHal system leads to β-halostyrenes. Similar procedure in the absence of a metal halide results in a cleavage of the C=C bond giving the corresponding benzaldehydes.
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v. Euler,Bernton
, p. 1720,1723 (1927)
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An efficient sonochemical oxidation of benzyl alcohols into benzaldehydes by FeCl3/HNO3 in acetone
Naik, Ramesh,Nizam, Aatika,Siddekha, Aisha,Pasha
, p. 1124 - 1127 (2011)
Sonochemical oxidation of benzyl alcohols into corresponding aldehydes by FeCl3/HNO3 in acetone at room temperature has been reported. All substrates give good yield of the products within 10-25 min. The reaction of selected substrates were also studied under reflux and at the room temperature. Further, various Lewis acids were used to evaluate their catalytic efficacy.
Design, synthesis and evaluation of phthalide alkyl tertiary amine derivatives as promising acetylcholinesterase inhibitors with high potency and selectivity against Alzheimer's disease
Cao, Zhongcheng,Deng, Yong,Li, Yan,Luo, Li,Qiang, Xiaoming,Song, Qing,Tan, Zhenghuai
, (2020)
A series of phthalide alkyl tertiary amine derivatives were designed, synthesized and evaluated as potential multi-target agents against Alzheimer's disease (AD). The results indicated that almost all the compounds displayed significant AChE inhibitory and selective activities. Besides, most of the derivatives exhibited increased self-induced Aβ1-42 aggregation inhibitory activity compared to the lead compound DL-NBP, and some compounds also exerted good antioxidant activity. Specifically, compound I-8 showed the highest inhibitory potency toward AChE (IC50 = 2.66 nM), which was significantly better than Donepezil (IC50 = 26.4 nM). Moreover, molecular docking studies revealed that compound I-8 could bind to both the catalytic active site and peripheral anionic site of AChE. Furthermore, compound I-8 displayed excellent BBB permeability in vitro. Importantly, the step-down passive avoidance test indicated that I-8 significantly reversed scopolamine-induced memory deficit in mice. Collectively, these results suggested that I-8 might be a potent and selective AChE inhibitor for further anti-AD drug development.
Electrophilic Aromatic Formylation with Bis-phenylthionium Ions
Smith, Robin A. J.,Bin Manas, Abdul Rahman
, p. 166 - 168 (1984)
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Iridium-catalyzed oppenauer oxidations of primary alcohols using acetone or 2-butanone as oxidant
Suzuki, Takeyuki,Morita, Kenji,Tsuchida, Mika,Hiroi, Kunio
, p. 1601 - 1602 (2003)
The first Oppenauer oxidation of primary alcohols with acetone or 2-butanone by an amino alcohol-based Ir bifunctional catalyst was accomplished. The reaction proceeds with 1 mol % catalyst in acetone or 2-butanone at 30-80 °C to give the corresponding aldehydes in 33-96% yield.
A PROCESS FOR THE PREPARATION OF VANILLIN AND OTHER SUBSTITUTED PHENYLALDEHYDES
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, (2022/01/12)
The present invention relates to a chemical process for the production of substituted phenylaldehydes such as vanillin (1a) from substituted phenylpropenes or substituted phenylpropenes enriched essential oils such as eugenol (2a) or eugenol rich essential oils indiscriminately through either cis or trans or a mixture of cis and trans isomer(s) of substituted phenylprop-2-enes such as isoeugenol, an intermediate compound. The invention relates to the conversion of substituted phenylpropenes to other substituted phenylaldehydes, particularly vanillin without the protection of the phenolic group, therefore, it offers a step economy. The present chemical process involves the use of class 3 and 4 solvents thereby devoid of the use of any chlorinated solvent.
Studies directed toward the synthesis of hedycoropyrans: total synthesis of des-hydroxy (?)-hedycoropyran B (ent-rhoiptelol B)
Kataria, Priyanka,Nomula, Rajesh,Kontham, Ravindar
, p. 444 - 463 (2022/01/20)
A full account of our efforts directed towards the synthesis of the diarylheptanoid-derived natural products hedycoropyrans that led to the total synthesis of ent-rhoiptelol B is described. In this endeavor, we have attempted two distinct synthetic strategies to access hedycoropyrans A and B, which led us to establish a facile synthetic route for des-hydroxy (?)-hedycoropyran B (ent-rhoiptelol B) from simple and readily accessible building blocks of 4-allylanisole and vanillin, employing Sharpless asymmetric epoxidation, CBS reduction, and an intramolecular AgOTf-catalyzed oxa-Michael reaction of suitably functionalized hydroxy-ynone as key transformations. The investigations disclosed herein will provide insights into designing novel synthetic routes for THP-DAH-derived natural products.
