5701-82-6

Usage

InChI:InChI=1/C22H14BrClN2O/c23-15-10-8-14(9-11-15)21-13-19(18-6-1-2-7-20(18)26-21)22(27)25-17-5-3-4-16(24)12-17/h1-13H,(H,25,27)

Upstream product

• 186581-53-3 diazomethane 
• 500-38-9 nordihydroguaiaretic acid 
• 67-71-0 dimethylsulfone 
• 54473-24-4 4-(4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl)benzene-1,2-diol 
• 4440-92-0 (2S*,3S*)-1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane-1,4-dione 
• 10352-25-7 (±)-secoisolariciresinol dimethyl ether 
• 126965-32-0 meso-1,2-bis[(3,4-dimethoxyphenyl)methyl]ethane-1,2-dicarboxylic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 126965-33-1 D,L-2,3-bis(3,4-dimethoxybenzyl)succinic acid anhydride 
• 73119-35-4 2,3-bis(3,4-dimethoxybenzylidene)butanedioic acid 
• 42923-56-8 veratrylidene-succinic acid dimethyl ester 
• 5507-27-7 3,4-dimethoxybenzylidenesuccinic acid 
• 335327-93-0 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethyl-2,3-butanediol 
• 776-99-8 3,4-dimethoxyphenylacetone 

Downstream Products

• 500-38-9 nordihydroguaiaretic acid 
• 27686-84-6 C₁₈H₂₂O₄ 

Relevant academic research and scientific papers

Modulation of expression of endothelial nitric oxide synthase by nordihydroguaiaretic acid, a phenolic antioxidant in cultured endothelial cells

Retrospective epidemiological studies have suggested that antioxidant therapy may decrease cardiovascular morbidity and mortality rates, although the mechanisms for this effect remain unclear. In the present study, we demonstrate that selective antioxidan

Novel synthetic method of nordihydroguaiaretic acid (NDGA)

Nordihydroguaiaretic acid has wide physiological activity and pharmacological activity. The invention discloses a novel synthetic method of nordihydroguaiaretic acid, wherein the method comprises thefollowing steps: carrying out reductive coupling reaction on veratone serving as a raw material under the action of a catalyst to obtain pinacol; reducing pinacol by trialkylsilane or triarylsilane under the catalysis of protonic acid or Lewis acid to generate 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane; and finally, under the action of haloid acid or Lewis acid, breaking ether bonds, and synthesizing nordihydroguaiaretic acid. The structure of the compound is characterized by 1H-NMR. Raw materials and reagents used in the method are easy to obtain, the reaction route is short, the reaction conditions are mild, the yield is high, the cost is low, and a simple and convenient path is opened up for industrial synthesis of nordihydroguaiaretic acid.

A short synthetic route to nordihydroguaiaretic acid (NDGA) and its stereoisomer using Ti-induced carbonyl-coupling reaction

A rapid synthetic approach to natural meso-nordihydroguaiaretic acid (NDGA) and its non-meso isomer is described from (3,4-dimethoxyphenyl)acetone using as a key step the low-valent Ti-induced carbonyl-coupling reaction of the ketone. The method involves

Syntheses of (+/-)-Deoxyschizandrin and the Lignan, 1,4-Bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane

(+/-)-Deoxyschizandrin (1) has been synthesised through a dimerisation reaction as a key step.The Grignard reagent from 1-(3,4,5-trimethoxyphenyl)-2-bromopropane (10) on reaction with 2-t-butyl-3-phenyloxaziridine gives 1,4-bis(3,4,5-trimethoxyphenyl)-2,3-dimethylbutane (11), which is cyclised using vanadium oxytrifluoride to get deoxyschizandrin (1).Following the above methodology, 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane (2), a lignan has also been prepared.

Optically active nordihydroguaiaretic acid and intermediates

A process for producing novel compositions including optically active molecules of nordihydroguaiaretic acid (d,1-2,3-dimethyl,1,4-bis(3,4-dihydroxyphenyl)butane) and intermediates, starting with 1,4-bis(3,4-dimethoxyphenyl)butanone, or other structurally similar composition having oxy substituents at the 3,4-phenyl positions, comprising (1) forming the corresponding butanol; (20) forming the corresponding 1,4-butane ether or siloxy composition; (3) cleaving the oxy substituent from the butane chain at the 1 and 4 positions; (4) dealkylating the phenols at the 3,4 positions to leave hydroxy substituents with hydrobromic acid reflux for 8 to 10 hours. Optical orientation is preserved throughout.

Structure of Malabaricanol - A Lignan from the Aril of Myristica malabarica Lam.

Malabaricanol, a lignan isolated from Myristica malabarica has been assigned the structure as β,β'-dimethyl-α,α'-bis(4-hydroxy-3-methoxyphenyl)tetrahydrofuran by spectroscopic and chemical methods.

The structure of chicanine, a new lignan from Schisandra sp.

A new lignan, chicanine, isolated from the fruit of Schisandra sp., is shown to possess structure 1, 2S-(3-methoxy-4-hydroxyphenyl)-3R,4S-dimethyl-5S-(3,4-methylenedioxyphenyl)tetrahydrofuran, from spectra analysis and chemical conversions.The tetrahydrof

SYNTHESIS OF A LIGNAN SKELETON VIA NICKEL- AND PALLADIUM-PHOSPHINE COMPLEX CATALYZED GRINGARD COUPLING REACTION OF HALOTHIOPHENES

A lignan skeleton is prepared in good yield through desulfurization of 3,4-dibenzylthiophene or 2,5-diaryl-3,4-dimethylthiophenes which are obtained by nickel- or palladium-phosphine complex catalyzed Gringard cross-coupling reaction of halothiophenes.