71721-74-9

Upstream product

• 100-02-7 4-nitro-phenol 
• 140-10-3 (E)-3-phenylacrylic acid 
• 14371-10-9 (E)-3-phenylpropenal 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 102-92-1 Cinnamoyl chloride 

Downstream Products

• 100-02-7 4-nitro-phenol 
• 140-10-3 (E)-3-phenylacrylic acid 
• 26829-64-1 (E)-cinnamoyl azide 
• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 35632-82-7 [(1E)-3-phenylbuta-1,3-dien-1-yl]benzene 
• 2123-92-4 (E)-tert-butyl 3-phenylprop-2-eneperoxoate 
• 122-97-4 3-Phenyl-1-propanol 
• 1009839-21-7 (E)-N′-cinnamoylbenzohydrazide 
• 1009839-16-0 C₁₅H₁₃N₃O₂ 
• 1138-15-4 cinnamoyl imidazole 
• 886-65-7 1,4-diphenyl-1,3-butadiene 

Relevant academic research and scientific papers

Lipophilic NHC assisted one-pot synthesis of syncarpamide analogues in aqueous medium

Lipophilic NHC catalysis in aqueous medium was reported for the synthesis of biologically relevant (a)symmetrically substituted and unsymmetrically substituted syncarpamide analogues. All the reported reactions were performed in the absence of any expensive metal salts or additives. A diverse array of syncarpamide analogues was obtained in good yields. Lipophilic NHC catalysis was also extended to chemoselective transesterification reactions.

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.

Olefins from biomass feedstocks: Catalytic ester decarbonylation and tandem Heck-type coupling

With the goal of avoiding the need for anhydride additives, the catalytic decarbonylation of p-nitrophenylesters of aliphatic carboxylic acids to their corresponding olefins, including commodity monomers like styrene and acrylates, has been developed. The reaction is catalyzed by palladium complexes in the absence of added ligands and is promoted by alkali/alkaline-earth metal halides. Combination of catalytic decarbonylation and Heck-type coupling with aryl esters in a single pot process demonstrates the viability of employing a carboxylic acid as a "masked olefin" in synthetic processes. This journal is

Palladium/NHC-catalyzed oxidative esterification of aldehydes with phenols

A palladium-catalyzed oxidative esterification of aldehydes with phenols is described, using air as the clean oxidant. This reaction tolerates many functional groups, providing esters with yields ranging from moderate to excellent.

Synthesis and antimycobacterial evaluation of new trans-cinnamic acid hydrazide derivatives

In this work, we report the synthesis and the antimycobacterial evaluation of new trans-cinnamic acid derivatives of isonicotinic acid series (5) and benzoic acid series (6), designed by exploring the molecular hybridization approach between isoniazid (1)

Aminolysis of Y-substituted phenyl X-substituted cinnamates and benzoates: Effect of modification of the nonleaving group from benzoyl to cinnamoyl

(Chemical Equation Presented) A kinetic study is reported for reactions of Y-substituted phenyl X-substituted cinnamates (1a-e and 3a-g) and benzoates (2a-e and 4a-g) with a series of alicyclic secondary amines in 80 mol % H 2O/20 mol % DMSO at

p-Toluenesulfonic acid mediated hydroarylation of cinnamic acids with anisoles and phenols under metal and solvent-free conditions

Hydroarylation of cinnamic acids with anisoles and phenols mediated by p-toluenesulfonic acid (p-TSA) under metal and solvent-free conditions gave 3-(4-methoxyphenyl)-3-phenylpropanoic acids and dihydrocoumarins, respectively, in high yields and excellent selectivity.

Pd-catalyzed decarbonylative olefination of aryl esters: Towards a waste-free Heck reaction

Easy and clean: A palladium (0)-catalyzed decarbonylative Heck olefination of activated esters of aryl, heteroaryl, and vinyl carboxylic acids opens up an opportunity for a novel waste-free Heck olefination process (see scheme).

Dendrimer poly(ethylenimine)s linked to β-cyclodextrin

β-Cyclodextrin was attached to two dendrimer poly(ethylenimine)s. The resulting cyclodextrin-containing dendrimers, CD-I and CD-II, can be considered either as dendrimers equipped with specific binding sites or as cyclodextrins containing amino groups around the cavities. Amines of CD-I and CD-II remarkably resisted protonation compared with those of the parent dendrimers. A compact conformation of CD-I or CD-II in which the dendrimer wraps itself around the cyclodextrin is proposed as a conformation consistent with the suppressed protonation. Esters containing t-butylphenyl groups were complexed by CD-I and CD-II and underwent fast deacylation. Kinetic data were obtained with several ester substrates, which revealed that two amino groups located in the vicinity of each cyclodextrin cavity of CD-I or CD-II participated as nucleophiles. In addition, optimum reactivity was attained when the spacer connecting the t-butylphenyl and the ester groups was -O- CH2- or -CH=CH-. Structures of the active sites for the accelerated deacylation of esters were elucidated on the basis of the kinetic data.

Participation of an Extended p-Oxo Ketene Intermediate in the Dissociative Alkaline Hydrolysis of Aryl 4-Hydroxycinnamates

The alkaline hydrolysis of 4-hydroxycinnamate esters of acidic phenols follows an E1cB mechanism and involves the participation of an "extended" p-oxo ketene intermediate.The apparent bimolecular rate constant (kaKa/Kw) for the hydrolysis of the 2,4-dinitrophenyl ester is some 2500-fold larger than that determined from the Hammett relationship for the BAc2 alkaline hydrolysis of substituted 2,4-dinitrophenyl cinnamates.The positive value of entropy of activation for the hydrolysis of 2,4-dinitrophenyl 4'-hydroxycinnamate and trapping experiments with nitrogen nucleophiles are consistent with the dissociative pathway.A change from a E1cB to a BAc2 mechanism is expected for esters with leaving groups having pKa higher than ca. 6.7.The higher E1cB reactivity of 2,4-dinitrophenyl 4'-hydroxycinnamate compared to that of the corresponding 4'-hydroxybenzoate is due to the vinylene group that further favors the dissociative route, probably increasing the stability of the unsaturated intermediate.