69731-27-7

Upstream product

• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 
• 2316-26-9 3,4-dimethoxycinnamic acid 
• 118199-01-2 2,2-dibromo-1-(3,4-dimethoxyphenyl)ethene 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 874518-74-8 4-(2-bromo-1-methoxy-ethyl)-1,2-dimethoxy-benzene 
• 97243-37-3 3-(3',4'-dimethoxyphenyl)-2,3-dibromopropanoic acid 
• 64-19-7 acetic acid 
• 5396-64-5 methyl (E)-3-(3,4-dimethoxyphenyl)acrylate 
• 2859-78-1 4-Bromoveratrole 

Downstream Products

• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 
• 134524-73-5 (E)-2-<2-(3,4-dimethoxyphenyl)ethenyl>-1-pyrrolidinecarboxaldehyde 
• 134486-37-6 [(E)-(R)-4-(3,4-Dimethoxy-phenyl)-1-methyl-2-oxo-but-3-enyl]-carbamic acid ethyl ester 
• 77669-22-8 2-(3,4-dimethoxyphenylethenyl)quinoline 
• 136114-02-8 (E)-1,2-dimethoxy-4-(2-methoxyethenyl)benzene 
• 67270-82-0 (E)-2-methoxy-4-(2-(pyrrolidin-2-yl)vinyl)phenol 
• 134524-76-8 (E)-2-methoxy-5-<2-pyrrolidin-2-ylethenyl>phenol 
• 1042728-03-9 C₁₃H₁₄N₂O₂ 
• 1042728-09-5 C₁₇H₁₆N₂O₂ 
• 1201221-01-3 (E)-1-(3,4-dimethoxyphenyl)-4-phenylbut-1-en-3-yne 
• 1206904-93-9 4-(2,2-dibromo-1-fluoroethyl)-1,2-dimethoxybenzene 
• 1180844-73-8 (E)-1-(4-(3,4-dimethoxystyryl)thiazol-2-yl)ethanone 
• 1180844-74-9 (E)-1-(4-(3,4-dimethoxystyryl)thiazol-2-yl)propan-1-one 
• 131699-18-8 methyl 5-(3,4-dimethoxyphenyl)pentanoate 

Relevant academic research and scientific papers

Nickel-Catalyzed, Regio- and Enantioselective Benzylic Alkenylation of Olefins with Alkenyl Bromide

A NiH-catalyzed migratory hydroalkenylation reaction of olefins with alkenyl bromides has been developed, affording benzylic alkenylation products with high yields and excellent chemoselectivity. The mild conditions of the reaction preclude olefinic products from undergoing further isomerization or subsequent alkenylation. Catalytic enantioselective hydroalkenylation of styrenes was achieved by using a chiral bisoxazoline ligand.

The hydrodebromination of 1,1-dibromoalkenes via visible light catalysis

Vinyl bromides are versatile synthetic intermediates and widely applied in organic synthesis and pharmaceuticals. Herein, a hydrodebromination reaction of 1,1-dibromoalkenes was established via visible light catalysis. A variety of structurally different vinyl bromides were obtained in moderate to excellent yields.

Stereoselective Synthesis of Vinyl Iodides through Copper(I)-Catalyzed Finkelstein-Type Halide-Exchange Reaction

An efficient method for the stereoselective synthesis of vinyl iodides is described. The reactions of vinyl bromides with potassium iodide proceed smoothly in the presence of a copper catalyst under mild reaction conditions to produce the corresponding vinyl iodides stereospecifically and in satisfactory to excellent yields.

Nickel-Catalyzed Reductive Cross-Coupling of Vinyl Bromides with Unactivated Alkyl Halides

The use of pyridine as the sole ligand for the reductive vinylation of unactivated secondary alkyl halides under Ni-catalyzed conditions has been developed. Both alkyl- and aryl-substituted vinyl bromides are suitable, in which alkyl-decorated α-alkenyl bromides resulted in the α-products in good results.

Tellurium-promoted stereoselective hydrodebromination of 1,1-dibromoalkenes: Synthesis of (: E)-bromoalkenes

We describe herein an efficient and simple method for the stereoselective hydrodebromination of 1,1-dibromoalkenes by using a catalytic amount of the nucleophilic species of tellurium, generated in situ by the reaction of elemental tellurium with NaBH4. By this methodology, (E)-bromoalkenes were obtained in moderate to excellent yields under mild reaction conditions, without the use of transition metals or base. Furthermore, a high stereoselectivity for the (E)-isomer was observed when 1,1-dibromoarylalkenes were used, thus indicating a promising alternative for future applications in organic synthesis.

Ni-catalyzed reductive coupling of α-halocarbonyl derivatives with vinyl bromides

This work describes the vinylation of α-halo carbonyl compounds with vinyl bromides under Ni-catalyzed reductive coupling conditions. While aryl-conjugated vinyl bromides entail pyridine as the sole labile ligand, the alkyl-substituted vinyl bromides require both bipyridine and pyridine as the co-ligands.

Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides

This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy-to-operate nickel-catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional-group tolerance. The nickel-catalytic system displays good chemoselectivity between the two C(sp2)-halide coupling partners, thus demonstrating a mechanistic pathway distinct from other stepwise protocols.

Total synthesis of tubastrine and 3-dehydroxy tubastrine by microwave-assisted cross-coupling reactions

The first syntheses of tubastrine and 3-dehydroxy tubastrine are described. The target compounds were prepared in four consecutive steps from commercially available starting materials. The central scaffold was formed by a microwave-assisted C-N cross-coupling reaction between 1,3-bis(tert-butoxycarbonyl)-guanidine and (E)-((4-(2-iodovinyl)-1,2-phenylene)bis(oxy))bis(tert-butyldimethylsilane) and (E)-tert-butyl(4-(2-iodovinyl)phenoxy)-dimethylsilane, respectively. The aryl vinyl iodides were obtained by a Hunsdiecker-Borodin-type reaction of aryl acrylic acids, which were easily available from trans-caffeic acid or trans-p-coumaric acid.

Nickel-catalyzed asymmetric reductive cross-coupling between vinyl and benzyl electrophiles

A Ni-catalyzed asymmetric reductive cross-coupling between vinyl bromides and benzyl chlorides has been developed. This method provides direct access to enantioenriched products bearing aryl-substituted tertiary allylic stereogenic centers from simple, stable starting materials. A broad substrate scope is achieved under mild reaction conditions that preclude the pregeneration of organometallic reagents and the regioselectivity issues commonly associated with asymmetric allylic arylation.

Restraining the flexibility of the central linker in terameprocol results in constrained analogs with improved growth inhibitory activity

The semi-synthetic lignan terameprocol inhibits the transcription of several inflammatory and oncogenic genes and has been evaluated for its anti-cancer properties. Here we investigated the effect of restricting the flexibility of the carbon linker connecting the terminal rings of terameprocol on its growth inhibitory activity. Conformational restriction was explored by introducing unsaturation, inserting polar entities with limited flexibility and cyclization of the connecting linker. Twenty three compounds were synthesized and evaluated on a panel of malignant human cells. The most promising compounds were those with non-polar linkers, as seen in butadiene 1a and the cyclized benzylideneindane analog 7. Both compounds were more potent than terameprocol on pancreatic BxPC-3 cells with GI50 values of 3.4 and 8.1 μM, respectively. Selected isomers of 1a (E,E) and 7 (Z) adopted low energy bent conformations that mimicked the low energy conformer of terameprocol. It is tempting to propose that conformational similarity to terameprocol may have contributed to their good activity. The scaffolds of 1a and 7 should be further investigated for their anticancer potential.