73789-34-1

Upstream product

• 102-92-1 cinnamoyl chloride 
• 106-48-9 4-chloro-phenol 
• 621-82-9 Cinnamic acid 
• 104-55-2 3-phenyl-propenal 
• 18736-43-1 4-nitro-phenyl cinnamate 
• 84796-16-7 C₁₇H₁₄O₃ 
• 85238-61-5 4-formylphenyl cinnamate 
• 73789-33-0 3,4-nitrophenyl cinnamate 
• 4067-21-4 2,4-nitrophenyl cinnamate 
• 3261-07-2 chloro-acetic acid-(4-chloro-phenyl ester) 
• 100-52-7 benzaldehyde 
• 140-10-3 (E)-3-phenylacrylic acid 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 

Downstream Products

• 1657-49-4 1-chloro-4-styrylbenzene 
• 106-48-9 4-chloro-phenol 
• 621-82-9 Cinnamic acid 
• 15719-64-9 methylammonium carbonate 
• 7778-83-8 cinnamic acid propyl ester 
• 246177-43-5 cinnamic acid diphenylmethyl ester 
• 3488-02-6 cinnamic acid 2-methoxyethyl ester 
• 40918-97-6 3-phenyl-2-propen-1-yl 3-phenylacrylate 
• 56961-72-9 cinnamic acid 1-phenylethyl ester 
• 63238-64-2 3-phenylacrylic acid phenethyl ester 
• 56289-55-5 allyl cinnamate 
• 103-41-3 benzy cinnamate 
• 7779-17-1 cinnamic acid cyclohexanol ester 
• 26829-64-1 (E)-cinnamoyl azide 

Relevant academic research and scientific papers

Kinetic study on aminolysis of aryl X-substituted-cinnamates in acetonitrile: Differential medium effect determines reactivity and reaction mechanism

A kinetic study on nucleophilic substitution reactions of 2,4-dinitrophenyl X-substituted-cinnamates (1a-1f) and Y-substituted-phenyl cinnamates (2a-2g) with a series of alicyclic secondary amines in MeCN at 25.0 ± 0.1 °C is reported. The Br?nsted-type pl

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.

Structure-reactivity correlations in nucleophilic displacement reactions of Y-substituted-phenyl X-substituted-cinnamates with Z-substituted-phenoxides

Second-order rate constants (kN) have been measured spectrophotometrically for the nucleophilic displacement reactions of 4-nitrophenyl X-substituted-cinnamates (4a-4e) and Y-substituted-phenyl cinnamates (5a-5e) with Z-substituted-phenoxide anions in 80 mol % H2O/20 mol % DMSO at 25.0 ±0.1 °C. The Hammett plot for the reactions of 4a-4e with 4-chlorophenoxide (4-ClPhO.) consists of two intersecting straight lines, which might be taken as a change in the rate-determining step (RDS). However, it has been concluded that the nonlinear Hammett plot is not due to a change in the RDS but is caused by stabilization of the ground state of substrates possessing an electron-withdrawing group in the cinnamoyl moiety through resonance interactions, since the Yukawa-Tsuno plot exhibits an excellent linear correlation with ρX = 0.89 and r = 0.58. The Bronsted-type plot for the reactions of 4-nitrophenyl cinnamate (4c) with Z-substituted-phenoxides is linear with βnuc = 0.76. The Bronsted-type plot for the reactions of Y-substituted-phenyl cinnamates (5a-5d) with 4-chlorophenoxides (4-ClPhO.) is also linear with βlg =.0.72. The Hammett plot correlated with σ-. constants for the reactions of 5a-5d results in a much better linear correlation than that correlated with σo constants, indicating that a partial negative charge develops on the O atom of the leaving aryloxide. Thus, the reactions have been concluded to proceed through a concerted mechanism.

NHC/Iron cooperative catalysis: Aerobic oxidative esterification of aldehydes with phenols

An NHC/iron cooperative catalytic system mediates the aerobic oxidative esterification of aldehydes with phenols. The use of equimolar amounts of reactants led to good to excellent isolated yields of esters.

Nucleophilic iron catalysis in transesterifications: Scope and limitations

Figure presented The ester bond is one of the most common structural motifs found in nature. Apart from the condensation between an acid and an alcohol, transesterifications represent another mechanistic alternative for the preparation of this compound class. The present paper summarizes our most recent investigations in this field, using nucleophilic iron complexes as catalysts for transesterifications under neutral conditions. This new type of metal catalyst complements the existing methodologies, which rely on Lewis acidic metal complexes. Investigations on scope and limitations, stereochemical course, and chemoselectivities will be presented.

PALLADIUM-CATALYZED ARYLOXYCARBONYLATION OF TERMINAL ALKYNES

Carbonylation of terminal alkynes using palladium-phosphine complexes proceeds efficiently in the presence of 3- or 4-substituted phenols to give the corresponding 2-substituted 2-propenoic acid aryl esters in good selectivity and yield.

Metal Ion Effects in Intramolecular Reactions. Effects of Divalent Metal Ions on Intramolecular Acetamido Group Participation in Ester Hydrolysis

The hydrolysis reactions of a series of esters of α-acetamidocinnamic acid proceed with formation of an oxazolinone intermediate.In 50percent dioxane-H2O (v/v) at 50 deg C, an oxazolinone can be observed spectrophotometrically in the OH- catalyzed cyclization reactions of the α-acetamido-substituted esters with leaving groups of pKa 12.4 or less.In comparison with the OH- catalyzed hydrolysis of the corresponding cinnamate esters, the rate enhancement due to the presence of the acetamido group is a factor of 200 with the trifluoroethyl ester and increases to 2x1E6 with the p-nitrophenyl ester.The plot of log kOH vs ?, the Hammett substituent constant, is linear and has a slope (ρ) of 2.7 (1.8 when ?- is employed) for the cyclization reactions of the phenolic esters, but the ρ value is only 1.4 for the OH- catalyzed hydrolysis of the corresponding cinnamates.The slope of log kOH vs the pKa of the leaving group for the cyclization of the α-acetamidocinnamic acid derivatives, βlg, is -0.9.Thus, there must be considerable C-O bond breaking in the critical transition state for oxazolinone formation.In H2O as the solvent, 6-carboxy-2-pyridylmethyl α-(N-acetylamino)cinnamate and the corresponding 2-pyridylmethyl derivative cyclize rapidly to the oxazolinone with KOH (5xE4)-fold larger than that for hydrolysis of 2-pyridylmethyl cinnamate, even though the leaving group is an aliphatic alcohol.There is significant metal ion catalysis in the cyclization reactions with Cu2+, Ni2+, Co2+ or Zn2+.The binding of the metal ions to the 6-carboxy-substituted derivative is very strong, and saturation occurs at metal ion concentrations less than 0.01 M.A saturating concentration of Cu2+ (0.001 M) enhances the rate of cyclization by a factor of 5x1E4.Thus, the total rate enhancement provided by bifunctional catalysis (Cu2+ and the neighboring acetamido group) is 1E9-fold.Metal ion binding to 2-pyridylmethyl α-(N-acetylamino)cinnamate is weak, but nevertheless, the second-order rate constants kOH are similar to those of the 6-carboxy-substituted ester at equal metal ion concentrations.The metal ions must exert their catalytic effect by stabilizing the leaving group alcohol in the transition state.This appears to be a general mechanism for metal ion catalysis of reactions in which C-O bond breaking is the rate-determining step.

Structure-Reactivity Relationships in Nucleophilic Reactions on Cinnamoyl Azide and Phenyl Cinnamates. Kinetic Stability of the Acyl Azide and Relative Leaving Ability of Nitrogen and Oxygen

The alkaline hydrolysis and aminolysis of cinnamoyl azide and aryl-substituted phenyl cinnamates and the azidolysis of the phenyl cinnamates have been studied.The positions of the rate-determining steps in the reactions are identified by the structure-reactivity relationships.The enhanced affinity of azide ion for an acyl carbon compared with its basicity is proposed to account for the observed kinetic stability of cinnamoyl azide toward alkaline hydrolysis and aminolysis.Azide ion resists expulsion from the tetrahedral intermediate more than quinuclidine derivatives but less than phenolates.This is explained in terms of the electron withdrawal as well as electron donation by resonance.