139214-80-5

Upstream product

• 556039-39-5 1,3-dimethyl-2-(2,3,4-trimethoxyphenyl)imidazolidine 
• 917497-32-6 6-bromo-2-hydroxy-3,4-dimethoxybenzaldehyde 
• 74-88-4 methyl iodide 
• 4885-02-3 Dichloromethyl methyl ether 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 
• 80141-07-7 methyl 6-bromo-2,3,4-trimethoxybenzoate 
• 139214-77-0 6-bromo-2,3,4-trimethoxybenzyl alcohol 

Downstream Products

• 1148134-72-8 C₁₀H₁₁⁽¹⁸⁾FO₄ 
• 917497-32-6 6-bromo-2-hydroxy-3,4-dimethoxybenzaldehyde 
• 139214-72-5 6-bromo-2,3,4-trimethoxybenzoic acid 
• 139214-81-6 6,6'-dibromo-2,2',3,3',4,4'-hexamethoxystilbene 

Relevant academic research and scientific papers

Access to 12-Membered Cyclic ortho, meta-Diarylheptanoids: Total Synthesis of Actinidione via Isomyricanone

We describe herein the first access to 12-membered cyclic[7,0]ortho,meta-diarylheptanoids. The key features of the synthesis include both a Suzuki-Miyaura coupling and a ring closing metathesis. Actinidione, a promising natural product, along with a bioac

6,7-Benzotropolone Syntheses Based on Ring-Closing Metatheses and Four-Electron Oxidations

Four homoallyl ortho-vinylaryl ketones (10a-d) – 1,8-dienes of sorts – were prepared by several approaches. In the presence of 1–2 mol-% Grubbs-II catalyst, they ring-closed to give 6,7-dihydrobenzocyclohepten-5-ones (11a-d) in 90–96 % yield. With SeO2 the parent compound (11a) delivered benzocyclohepten-5-one (13a) and/or selenium-containing compounds (18–22) but no more than traces of 6,7-benzotropolone (5a). However, 5a was accessible from compound 11a via the sodium enolate and allowing it to react with a stream of oxygen (43 % yield). The sodium enolates of the substituted 6,7-dihydrobenzocyclohepten-5-ones 11b–d and oxygen underwent analogous 4-electron oxidations. This furnished the substituted 6,7-benzotropolones 11b-d. In contrast, the corresponding lithium enolates were inert towards oxygen. The 6,7-dihydrobenzocyclohepten-5-one 11d was also accessed differently, namely by a Grubbs-II catalyst-mediated RCM/C=C migration tandem reaction of the allyl ortho-allylaryl ketone 73 – another 1,8-diene of sorts (90 % yield).

A novel selenoflavone compound as anti-obesity agent

The present invention relates to a process for producing a novel selenoflavone compound and a pharmaceutical composition for preventing or treating obesity comprising the selenoflavone compound. In the present invention, selenoflavone, especially PMSF, which has never been synthesized due to synthetic difficulties can be synthesized through palladium-catalyzed direct C-H arylation. Since the synthesized selenoflavone has an improving effect related to activation of brown adipose tissue (BAT), the selenoflavone can be used in the composition for prevention and treatment of obesity.COPYRIGHT KIPO 2018

Efficient synthesis of polymethoxyselenoflavones via regioselective direct C-H arylation of selenochromones

Substantial research has suggested that the configuration and the total number of functional groups on flavones influence their bioactivity. To investigate the changes in the biological activities of selenoflavones in relationship to structural changes, the development of a generally applicable synthetic method was a key. Until now, an efficient pathway for palladium-catalyzed direct arylation with the selenocyclic enone systems is not known in the literature. We herein introduce a simple direct C-H arylation of two difficult coupling partners, selenochromones and electron-rich aryl bromide, affording diverse polymethoxyselenoflavones with great efficiency and high selectivity.

Nucleophilic substitution of nitro groups by [18F]fluoride in methoxy-substituted ortho-nitrobenzaldehydes-A systematic study

As model reactions for the introduction of [18F]fluorine into aromatic amino acids, the replacement of NO2 by [18F]fluoride ion in mono- to tetra-methoxy-substituted ortho-nitrobenzaldehydes was systematically investigated. Unexpectedly, the highly methoxylated precursors 2,3,4-trimethoxy-6-nitrobenzaldehyde and 2,3,4,5-tetramethoxy-6-nitrobenzaldehyde showed high maximum radiochemical yields (82% and 48% respectively). When the electrophilicity of the leaving group substituted carbon atom is expressed by its 13C NMR chemical shift a good correlation with the reaction rate at the beginning of the reaction (first min) was found (R2 = 0.89), whereas the maximum radiochemical yields correlated much poorer with this electrophilicity parameter. This may be caused by side reactions becoming influencial in the further reaction course. As possible side reactions the demethylation of methoxy groups and intramolecular redox reactions could be detected by HPLC/MS.

A short total synthesis of the alkaloids piperolactam C, goniopedaline, and stigmalactam

The total synthesis of the polyalkoxylated alkaloids piperolactam C, goniopedaline and stigmalactam by combinatorial metalation/cyclization strategies has been achieved. The synthetic route involved the preliminary construction of the polyalkoxylated isoindolinone template by Parham's technique. Benzylic lactam deprotonation allowed connection of a hydroxybenzyl appendage, and the synthesis of the target natural products was completed by subsequent E1cB elimination, radical cyclization and final deprotection. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

On the Synthesis of a Phenanthrene-2,7-quinone

Oxidative coupling of 2,2',4,4'-tetramethoxystilbene-3,3'-diol 51 gave a 51percent yield of 1,3,6,8-tetramethoxyphenanthrene-2,7-quinone 52, the first isolated example of a quinone of this type.Similar oxidation of the corresponding diphenylethane 55 gave