31416-74-7

Upstream product

• 78-83-1 2-methyl-propan-1-ol 
• 140-10-3 (E)-3-phenylacrylic acid 
• 102-92-1 Cinnamoyl chloride 
• 106-63-8 isobutyl acrylate 
• 71-43-2 benzene 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 108-86-1 bromobenzene 
• 100-42-5 styrene 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 21947-71-7 cinnamic anhydride 
• 591-50-4 iodobenzene 

Downstream Products

• 26029-32-3 4,4-dimethyl-3-phenyl-cyclopent-2-enone 
• 173142-22-8 1,5-Dichloro-4,8-diphenyltricyclo[5.1.0.0^3,5]octane-2,6-dione 
• 122-97-4 3-Phenyl-1-propanol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 

Relevant academic research and scientific papers

Ruthenium-Catalyzed Oxidative Cross-Coupling Reaction of Activated Olefins with Vinyl Boronates for the Synthesis of (E, E)-1,3-Dienes

An oxidative cross-coupling reaction between activated olefins and vinyl boronate derivatives has been developed for the highly stereoselective construction of synthetically useful (E,E)-1,3-dienes. The highlight of this reaction is that exclusive stereoselectivity (only E,E-isomer) was achieved from a base-free, ligand-free, and mild catalytic condition with a less expensive [RuCl2(p-cymene)]2 catalyst.

Preparation method of cinnamate in eutectic solvent (by machine translation)

The invention discloses a method for preparing cinnamate from a eutectic solvent. A mol of choline chloride, B mol of methanesulfonic acid (p-toluenesulfonic acid) was added to a dry three-port flask, stirred at room temperature for eutectic solvent, C mol of cinnamic acid, D mol of alcohol, 50 °C for reaction, TLC was monitored until reaction was complete. After the completion of the reaction, the reaction liquid is poured into water, extracted with dichloromethane, the organic phase is distilled off to obtain a cinnamate, and the aqueous phase is recovered to obtain a eutectic solvent. The method does not need an organic solvent, and is simple to operate, high in yield, high in product purity, short in reaction time, simple in post-treatment, environmentally friendly and low in cost. (by machine translation)

Bioactivity and structure–activity relationship of cinnamic acid derivatives and its heteroaromatic ring analogues as potential high-efficient acaricides against Psoroptes cuniculi

A series of cinnamic acid derivatives and its heteroaromatic ring analogues were synthesized and evaluated for acaricidal activity in vitro against Psoroptes cuniculi, a mange mite. Among them, eight compounds showed the higher activity with median lethal concentrations (LC50) of 0.36–1.07 mM (60.4–192.1 μg/mL) and great potential for the development of novel acaricidal agent. Compound 40 showed both the lowest LC50 value of 0.36 mM (60.4 μg/mL) and the smallest median lethal time (LT50) of 2.6 h at 4.5 mM, comparable with ivermectin [LC50 = 0.28 mM (247.4 μg/mL), LT50 = 8.9 h], an acaricidal drug standard. SAR analysis showed that the carbonyl group is crucial for the activity. The type and chain length of the alkoxy in the ester moiety and the steric hindrance near the ester group significantly influence the activity. The esters were more active than the corresponding thiol esters, amides, ketones or acids. Replacement of the phenyl group of cinnamic esters with α-pyridyl or α-furanyl significantly increase the activity. Thus, a series of cinnamic esters and its heteroaromatic ring analogues with excellent acaricidal activity emerged.

Synthesis of (E)-cinnamyl ester derivatives via a greener Steglich esterification

Cinnamic acid derivatives are known antifungal, antimicrobial, antioxidant, and anticancer compounds. We have developed a facile and mild methodology for the synthesis of (E)-cinnamate derivatives using a modified Steglich esterification of (E)-cinnamic acid. Using acetonitrile as the solvent, rather than the typical chlorinated solvent, and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) as the coupling agent enables ester conversion in 45 min with mild heating (40–45 °C) and an average yield of 70% without need for further purification. These conditions were used to couple (E)-cinnamic acid with 1° and 2° aliphatic alcohols, benzylic and allylic alcohols, and phenols. This work demonstrates a facile and greener methodology for Steglich esterification reactions.

A highly efficient Pd/CuI-catalyzed oxidative alkoxycarbonylation of α-olefins to unsaturated esters

A new protocol for the alkoxycarbonylation of α-olefins to the corresponding unsaturated esters has been developed. Differently substituted styrenes were selectively converted to cinnamate derivatives, via C[sbnd]H bond functionalization. Various palladium sources, including heterogeneous ones, in combination with CuI exhibited a high catalytic efficiency using oxygen as the most cheap oxidant. Monocarbonylated products were obtained in good yields and high chemoselectivity working with a low CO pressure (2 atm) and an excess of air (35 atm) avoiding in this way explosion risks. Commercial cinnamate derivatives were prepared in good to excellent yields by this very simple one-pot procedure.

Design, synthesis, and preliminary evaluation of substituted cinnamic acid esters as selective matrix metalloproteinase inhibitors

Strategy, Management and Health Policy Preclinical Research Substituted cinnamic acid esters with extended P1' groups were synthesized using microwave irradiation and tested for their inhibitory activities on matrix metalloproteinase (MMP)-1, MMP-2, and MMP-9. Preliminary structure-activity relationship analysis and docking studies showed that hydroxyl groups in the benzene ring and the presence of extended spatial structures in the carboxylic acid played key roles in the MMP-2 and MMP-9 inhibitory activity and selectivity over MMP-1.

Efficient esterification of carboxylic acids with alcohols by hydrogen peroxide as a novel condensing agent

Esterification of carboxylic acids with different alcohols has been achieved in presence of catalyst hydrogen peroxide and sulphuric acid. This method is free from disadvantages of base catalyst and high temperature. Hydrogen peroxide with sulphuric acid increases the yield up to 98 % with minimum side products. Several esters were synthesized by this method by condensing carboxylic acids (1) with alcohols (2) in presence of hydrogen peroxide and sulphuric acid.

Palladium(II)-catalyzed catalytic aminocarbonylation and alkoxycarbonylation of terminal alkynes: Regioselectivity controlled by the nucleophiles

The aminocarbonylation and alkoxycarbonylation reactions of terminal alkynes took place smoothly and efficiently using a catalyst system Pd(OAc) 2-dppb-p-TsOH-CH3CN-CO under relatively mild experimental conditions. The catalytic system was tested and optimized using two different nucleophiles: alcohols and amines. Phenylacetylene (1a) was considered as an alkyne along with diisobutylamine (2b1) andmethanol (2c1) as nucleophiles. The results showed significant differences in the conversion of 1a and in the selectivity towards the gem or trans unsaturated esters or amides with these nucleophiles. The effects of the type of palladium catalysts, the type of ligands, the amount of dppb and the solvents were carefully studied. With diisobutylamine (2b1), excellent regioselectivity towards the 2-acrylamides (gem isomer, 3ab1) was almost always observed, while trans-α,β-unsaturated esters 4ac1 was the predominant product with methanol (2c1) as a nucleophile. This remarkable sensitivity in the selectivity of the reaction indicates two different possible mechanistic pathways for these carbonylation reactions. Copyright

A titania-supported highly dispersed palladium nano-catalyst generated via in situ reduction for efficient Heck coupling reaction

Supported metal catalysts have been applied in many current industrial processes. The dispersion of metal particles on solid supports has been proven to affect the performance of catalysts greatly. In this study, a titania-supported palladium catalyst prepared by a simple pH-controlled adsorption method is efficient and recyclable for the Heck coupling reaction of aryl halides and alkenes. The pH-controlled adsorption method results in high dispersion of palladium species on titania surface. During the reaction, palladium nanoparticles are in situ generated via reduction on the surface of titania. TEM images indicate that the nanoparticles are nearly monodisperse in size. Recycling studies have shown that the catalyst can be readily recovered and reused several times without significant loss of catalytic activity.

Pd(OAc)2-Catalyzed Oxidative Coupling Reaction of Benzenes with Olefins in the Presence of Molybdovanadophosphoric Acid under Atmospheric Dioxygen and Air

The direct oxidative coupling reaction of benzenes with alkenes bearing an electron-withdrawing group was successfully achieved by the use of Pd(OAc) 2/molybdovanadophosphoric acid (HPMoV) as the key catalyst under O2 or air atmosphere. Thus, the reaction of benzene with ethyl acrylate under air (1 atm) assisted by Pd(OAc)2/HPMoV afforded ethyl cinnamate as a major product in satisfactory yield (74%). This catalytic system could be extended to the coupling reactions between various substituted benzenes and alkenes through the direct aromatic C-H bond activation. In the reaction of benzene with ethyl acrylate under O2 (1 atm), the best turn-over number (TON) of Pd(OAc)2 reached was 121. This reaction provides a green route to cinnamate derivatives, which are important precursors of a variety of pharmaceuticals.