6302-60-9

Usage

InChI:InChI=1/C12H16O3/c1-9(13)4-5-10-6-7-11(14-2)12(8-10)15-3/h6-8H,4-5H2,1-3H3

Upstream product

• 61914-52-1 1-(3,4-dimethoxyphenyl)-5-hydroxydecan-3-one 
• 128156-34-3 4-(3,4-Dimethoxy-benzyl)-3-methyl-2H-isoxazol-5-one 
• 128156-28-5 (4Z)-4-(3,4-dimethoxybenzylidene)-3-methylisoxazol-5(4H)-one 
• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 153993-01-2 tert-Butyl-[3-(3,4-dimethoxy-phenyl)-1-methylene-propoxy]-dimethyl-silane 
• 60234-90-4 4-(3,4-dimethoxy-phenyl)-but-3-en-2-one 
• 51842-87-6 3-(3,4-dimethoxy-phenyl)-propionyl chloride 
• 75-24-1 trimethylaluminum 
• 77-78-1 dimethyl sulfate 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 122-48-5 4-(4-hydroxy-3-methoxyphenyl)-2-butanone 
• 74-88-4 methyl iodide 
• 23513-14-6 (+/-)-[6]-gingerol 

Downstream Products

• 61871-73-6 methylzingerone trimethylsilyl ether 
• 81580-10-1 5-{2-[3-(3,4-Dimethoxy-phenyl)-1-methyl-propylamino]-1-hydroxy-ethyl}-2-hydroxy-benzamide 
• 91998-04-8 (+/-)-di-O-methyl hexahydrocurcumin 
• 77741-94-7 [3-(3,4-Dimethoxy-phenyl)-1-methyl-propyl]-(6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine 
• 153993-01-2 tert-Butyl-[3-(3,4-dimethoxy-phenyl)-1-methylene-propoxy]-dimethyl-silane 
• 57507-12-7 5-(3,4-Dimethoxy-phenyl)-3-methyl-pent-1-yn-3-ol 
• 188476-32-6 4-((E)-4-Allyloxy-3-methyl-but-3-enyl)-1,2-dimethoxy-benzene 
• 79622-76-7 3,4-Dimethoxy-(3'-hydroxybutyl)-benzol 
• 75-25-2 Bromoform 
• 2107-70-2 3,4-methoxycinnamic acid 
• 860518-51-0 1,3,5-tris-(3,4-dimethoxy-phenethyl)-benzene 
• 93-07-2 Veratric acid 
• 838846-23-4 2-[2-(3,4-dimethoxy-phenyl)-ethyl]-2-methyl-pent-4-enal 
• 77741-89-0 6-[3-(3,4-Dihydroxy-phenyl)-1-methyl-propylamino]-5,6,7,8-tetrahydro-naphthalene-2,3-diol; hydrobromide 

Relevant academic research and scientific papers

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.

Photoredox-Catalyzed Simultaneous Olefin Hydrogenation and Alcohol Oxidation over Crystalline Porous Polymeric Carbon Nitride

Booming of photocatalytic water splitting technology (PWST) opens a new avenue for the sustainable synthesis of high-value-added hydrogenated and oxidized fine chemicals, in which the design of efficient semiconductors for the in-situ and synergistic utilization of photogenerated redox centers are key roles. Herein, a porous polymeric carbon nitride (PPCN) with a crystalline backbone was constructed for visible light-induced photocatalytic hydrogen generation by photoexcited electrons, followed by in-situ utilization for olefin hydrogenation. Simultaneously, various alcohols were selectively transformed to valuable aldehydes or ketones by photoexcited holes. The porosity of PPCN provided it with a large surface area and a short transfer path for photogenerated carriers from the bulk to the surface, and the crystalline structure facilitated photogenerated charge transfer and separation, thus enhancing the overall photocatalytic performance. High reactivity and selectivity, good functionality tolerance, and broad reaction scope were achieved by this concerted photocatalysis system. The results contribute to the development of highly efficient semiconductor photocatalysts and synergistic redox reaction systems based on PWST for high-value-added fine chemical production.

Synthesis of Vicinal Quaternary All-Carbon Centers via Acid-catalyzed Cycloisomerization of Neopentylic Epoxides

We report our studies on the development of a catalytic cycloisomerization of 2,2-disubstituted neopentylic epoxides to produce highly substituted tetralins and chromanes. Termination of the sequence occurs via Friedel-Crafts-type alkylation of the remote (hetero)arene linker. The transformation is efficiently promoted by sulfuric acid and proceeds best in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as the solvent. Variation of the substitution pattern provided detailed insights into the migration tendencies and revealed a competing disproportionation pathway of dihydronaphthalenes.

One-Pot, Tandem Wittig Hydrogenation: Formal C(sp3)-C(sp3) Bond Formation with Extensive Scope

A one-pot, tandem Wittig hydrogenation of aldehydes with stabilized ylides is reported, representing a formal C(sp3)-C(sp3) bond construction. The tandem reaction operates under mild conditions, is high yielding, and is broad in scope. Chemoselectivity for olefin reduction is observed, and the methodology is demonstrated in the synthesis of lapatinib analogues and a formal synthesis of (±)-cuspareine. Early insights suggest that the chemoselectivity observed in the reduction step is due to partial poisoning of the catalyst, after step one, thus adding to the power of the one-pot procedure.

Synthesis, docking, cytotoxicity, and LTA4H inhibitory activity of new gingerol derivatives as potential colorectal cancer therapy

Leukotriene A4 hydrolase (LTA4H) is a proinflammatory enzyme that generates the inflammatory mediator leukotriene which may play an important role in chronic inflammation associated carcinogenesis. [6]-gingerol, the major bioactive compound of Zingiber officinale, is a potential inhibitor of LTA4H, a highly expressed enzyme in colorectal carcinoma. Eighteen compounds; seven of natural origin (including [4]-, [6]-, [8]-, and [10]-gingerol), five new and six known semi-synthesized [6]-gingerol derivatives were examined using docking, in vitro cytotoxicity against human colon cancer cells (HCT-116) and LTA4H aminopeptidase and epoxide hydrolase inhibitory studies. Methyl shogoal (D8) showed to be the most potent compound against HCT-116 cells (IC50; 1.54?μM). Remarkably, D8 proved to be non-cytotoxic to normal cells; (TIG-1) and (HF-19) with high selective index (SI; 52.3). Furthermore [6]-gingerol derivatives showed potent LTA4H inhibitory activities in comparison to the universal positive controls (bestatin and 4BSA). Among the natural gingerols, [10]-gingerol (N3) exhibited the highest LTA4H aminopeptidase and epoxide hydrolase inhibitory activities with IC50; 21.59 and 15.24?μM, respectively. Meanwhile, methyl shogoal (D8) and 4′-O-prenyl-[6]-gingerol (D10) retained the highest inhibition with IC50; 4.92 and 3.01?μM, for aminopeptidase, and 11.27 and 7.25?μM for epoxide hydrolase activities, respectively.

Structure-Activity Relationships of 6- and 8-Gingerol Analogs as Anti-Biofilm Agents

Pseudomonas aeruginosa is a causative agent of chronic infections in immunocompromised patients. Disruption of quorum sensing circuits is an attractive strategy for treating diseases associated with P. aeruginosa infection. In this study, we designed and synthesized a series of gingerol analogs targeting LasR, a master regulator of quorum sensing networks in P. aeruginosa. Structure-activity relationship studies showed that a hydrogen-bonding interaction in the head section, stereochemistry and rotational rigidity in the middle section, and optimal alkyl chain length in the tail section are important factors for the enhancement of LasR-binding affinity and for the inhibition of biofilm formation. The most potent compound 41, an analog of (R)-8-gingerol with restricted rotation, showed stronger LasR-binding affinity and inhibition of biofilm formation than the known LasR antagonist (S)-6-gingerol. This new LasR antagonist can be used as an early lead compound for the development of anti-biofilm agents to treat P. aeruginosa infections.

Lipase behavior in the stereoselective transesterification of zingerol-like derivatives and related biphenyls

Using a highly stereoselective enzymatic procedure based on the irreversible transesterification of alcoholic functions in organic solvent, both enantiomers of zingerol and dehydrozingerol O-methyl derivatives 1 and 2 were obtained in high optical purity. The biocatalytic method was then extended to the corresponding biphenyl derivatives 5-8 for which an one-pot resolution/desymmetrization was carried out on the whole racemic/meso mixtures to give single stereoisomers with very high enantiomeric and diastereoisomeric excesses. The comparison of kinetic and enantioselective behavior of the lipase AK from Pseudomonas fluorescens in the transesterification of monomer (±)-1 and the related (±)-5 and meso-6 biphenyl dimers was also made.

Synthesis and neuroprotective effect of E-3,4-dihydroxy styryl aralkyl ketones derivatives against oxidative stress and inflammation

E-3,4-Dihydroxy styryl aralkyl ketones as well as their 3,4-diacetylated derivatives as the analogues of neuroprotective agent CAPE were designed and synthesized for improving stability and lipid solubility. The neuroprotective activities of target compounds 10a-g and 11a-g were tested by three models in vitro, including 1,1-diphenyl-2-picrylhydrazyl radical scavenging capacity, neuronal protecting effect against damage induced by H2O2 in PC12 cells and nitric oxide suppression effect in BV2 microglial cells. The results demonstrated that compounds 10f and 11f exhibited the most potent neuroprotective effect against oxidative stress and inflammation, which is higher than that of the lead compound CAPE.

Novel diarylheptanoids as inhibitors of TNF-α production

Synthesis and anti-inflammatory activity of novel diarylheptanoids [5-hydroxy-1-phenyl-7-(pyridin-3-yl)-heptan-3-ones and 1-phenyl-7-(pyridin-3-yl) hept-4-en-3-ones] as inhibitors of tumor necrosis factor-α (TNF-α) production is described in the present article. The key reactions involve the formation of a β-hydroxyketone by the reaction of substituted 4-phenyl butan-2-ones with pyridine-3-carboxaldehyde in presence of LDA and the subsequent dehydration of the same to obtain the α,β-unsaturated ketones. Compounds 4i, 5b, 5d, and 5g significantly inhibit lipopolysaccharide (LPS)-induced TNF-α production from human peripheral blood mononuclear cells in a dose-dependent manner. Of note, the in vitro TNF-α inhibition potential of 5b and 5d is comparable to that of curcumin (a naturally occurring diarylheptanoid). Most importantly, oral administration of 4i, 5b, 5d, and 5g (each at 100 mg/kg) but not curcumin (at 100 mg/kg) significantly inhibits LPS-induced TNF-α production in BALB/c mice. Collectively, our findings indicate that these compounds may have potential therapeutic implications for TNF-α-mediated auto-immune/inflammatory disorders.

Hypervalent iodine(III)-induced intramolecular cyclization reaction of substituted phenol ethers with an alkyl azido side-chain: A novel and efficient synthesis of quinone imine derivatives

Novel and efficient syntheses of quinone imine ketals (2aj) and quinone imines (4ah) from substituted phenol ethers (1ak) bearing an alkyl azido side-chain using the combination of hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA) and trimethylsilyl trifluoromethanesulfonate (TMSOTf), have been developed.