5273-94-9

Upstream product

• 32977-07-4 2-allyl-3,5-dimethoxyphenol 
• 77-78-1 dimethyl sulfate 
• 500-99-2 3,5-dimethoxyphenol 
• 106-95-6 allyl bromide 
• 32977-06-3 1-(allyloxy)-3,5-dimethoxybenzene 
• 74-88-4 methyl iodide 
• 621-23-8 1,2,3-trimethoxybenzene 
• 556-56-9 allyl iodid 
• 570-02-5 2,4,6-trimethoxybenzoic acid 
• 4873-09-0 allyl tosylate 
• 762-72-1 allyl-trimethyl-silane 
• 186581-53-3 diazomethane 

Downstream Products

• 5273-96-1 (E)-1,3,5-trimethoxy-2-(prop-1-en-1-yl)benzene 
• 5273-95-0 (Z)-1,3,5-trimethoxy 2-(prop-1-enyl)benzene 

Relevant academic research and scientific papers

Selective Claisen rearrangement and iodination for the synthesis of polyoxygenated allyl phenol derivatives

Allyl aryl ethers and allyl phenol derivatives were prepared starting from commercial or synthetized phenols. Either Williamson reaction or Et2AlCl catalyzed Claisen rearrangement was performed to obtain the polyoxygenated molecules. The pivotal allyl phenols were then modified by methylation, iodocyclization or electrophilic aromatic iodination to afford the polyoxygenated derivatives in good to excellent yields. Additionally, their antibacterial properties were also investigated against Gram-positive and Gram-negative bacteria.

2-Prenylated m-dimethoxybenzenes as potent inhibitors of 15-lipo-oxygenase: inhibitory mechanism and SAR studies

15-lipo-oxygenases are one of the iron-containing proteins capable of performing peroxidation of unsaturated fatty acids in animals and plants. The critical role of enzymes in the formation of inflammations, sensitivities, and some cancers has been demonstrated in mammals. The importance of enzymes has led to the development of mechanistic studies, product analysis, and synthesis of inhibitors. In this study, a series of allyl and prenyl dimethoxybenzenes were synthesized and their inhibitory potency against soybean 15-Lipo-oxygenase (L1; EC 1,13,11,12) was determined. Among the synthetic compounds, 2,6-dimethoxy-1-isopentenyl-4-methylbenzene, 2,6-dimethoxy-1-geranyl-4-methylbenzene, and 2,6-dimethoxy-1-farnesyl-4-methylbenzene showed the most potent inhibitory activity with IC50 values of 7.6, 5.3, and 0.52?μm, respectively. For some of the compounds, SAR studies showed acceptable relationship between inhibitory potency and enzyme–ligand interactions. Radical scavenging assessment results apart from the SAR studies indicate that electronic properties are the major factors for lipo-oxygenase inhibition potency of the mentioned compounds. Based on the theoretical studies, it was suggested that CH…O intramolecular hydrogen bond between ortho-methoxy oxygen and methine hydrogen atoms is one of the major factors in the stability of 2,6-dimethoxyallyl(or prenyl)benzenes radical via the planarity fixation between phenyl and allyl (or prenyl) pi orbitals.

Bicatalytic allylation-cross-metathesis reactions as γ-carbonyl cation equivalents

The products corresponding to the reactions of arenes and γ-carbonyl cations may be obtained by a one-pot, bicatalytic process involving InCl 3-catalyzed arene allylation and cross metathesis with electron-deficient alkenes. The process is successful with electronically neutral and electron-rich arenes, and modestly Lewis basic donor groups are tolerated with an increase in InCl3 loading from 10 mol% to 15 mol%, and in one case, 20 mol%. Georg Thieme Verlag Stuttgart · New York.

Pd(ii)-catalyzed decarboxylative allylation and Heck-coupling of arene carboxylates with allylic halides and esters

This work demonstrates an alternative method to prepare allylated arenes and aryl-substituted allylic esters via catalytic decarboxylative C-C bond formation using aromatic carboxylic acids and allylic halides and esters.

Rhodium- and iridium-catalyzed allylation of electron-rich arenes with allyl tosylate

The allylation of electron-rich arenes with allyl tosylate proceeded at 0°C in the presence of [Rh(nbd)(CH3CN)2]PF 6. Various oxygenated arenes were allylated with high para-selectivity in almost all cases. Especially in t

STRUCTURE-ACTIVITY RELATIONSHIPS OF PHENYLPROPANOIDS AS GROWTH INHIBITORS OF THE GREEN ALGA SELENASTRUM CAPRICORNUTUM

Twenty-seven commercial or synthetic phenylpropanoids have been tested in broth against the unicellular alga Selenastrum capricornutum.The antialgal activity seems to be linked to the number as well as to the position of the methoxyl group in the molecule.A slight effect of the side chain substitution was also observed. Key Word Index - Selenastrum capricornutum; allelochemicals; phenylpropanoids.

IRON-MEDIATED AROMATIC ALLYLATION

Electron rich aromatic and heteroaromatic compounds react with (η3-allyl)Fe(CO)4BF4 to produce allylated aromatics in moderate to good yields.Unsymmetrically substituted allyl complexes afford the corresponding butenyl-, 1,1-dimethylallyl-, cinnamyl-, and geranyl-derivatives with moderate to excellent regioselectivity and complete stereoselectivity.

UMPOLUNG OF REACTIVITY OF ALLYLSILANE, ALLYLGERMANE, AND ALLYLSTANNANE VIA THEIR REACTION WITH THALLIUM (III) SALT: A NEW ALLYLATION REACTION FOR AROMATIC COMPOUND

A new direct allylation of the aromatic compound has been developed.A combination of allylsilane, allylgermane, or allylstannane and thallium (III) trifluoroacetate gave rise to an allyl cationic species which was allowed to react with an aromatic compound, a nucleophile, to give allylation product(s) in good yields.