85238-61-5

Upstream product

• 102-92-1 cinnamoyl chloride 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 539022-23-6 (Z)-3-Phenyl-acrylic acid 4-((E)-3-oxo-3-thiophen-2-yl-propenyl)-phenyl ester 
• 539022-22-5 (Z)-3-Phenyl-acrylic acid 4-((E)-3-naphthalen-1-yl-3-oxo-propenyl)-phenyl ester 
• 539022-18-9 (Z)-3-Phenyl-acrylic acid 4-[(E)-3-(2-bromo-phenyl)-3-oxo-propenyl]-phenyl ester 
• 539022-20-3 (Z)-3-Phenyl-acrylic acid 4-[(E)-3-(4-chloro-phenyl)-3-oxo-propenyl]-phenyl ester 
• 539022-19-0 (Z)-3-Phenyl-acrylic acid 4-[(E)-3-(4-bromo-phenyl)-3-oxo-propenyl]-phenyl ester 
• 331459-99-5 (Z)-3-Phenyl-acrylic acid 4-((E)-3-oxo-3-phenyl-propenyl)-phenyl ester 
• 331460-44-7 1-(p-methylphenyl)-3-(4'-cinnamoyloxyphenyl)-2-propen-1-one 
• 539022-21-4 1-(p-methoxyphenyl)-3-(4'-cinnamoyloxyphenyl)-2-propen-1-one 
• 73789-34-1 cinnamic acid 4-chlorophenyl ester 
• 24561-34-0 C₁₃H₁₃NO₃ 
• 123-08-0 4-hydroxy-benzaldehyde 

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

Effect of azo and ester linkages on rod shaped Schiff base liquid crystals and their photophysical investigations

Two new series of rod shaped Schiff base containing liquid crystal compounds with azo and ester linkages have been synthesized and characterized respectively. The rod like molecules containing cinnamate linkages with four different alkyl spacers (n?=?6, 8

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.

The α-effect in nucleophilic substitution reactions of Y-substituted-Phenyl X-substituted-cinnamates with Butane-2,3-dione monoximate

Second-order rate constants (kOx-) have been measured spectrophotometrically for nucleophilic substitution reactions of 4-nitrophenyl X-substituted-cinnamates (7a-7e) and Y-substituted-phenyl cinnamates (8a-8e) with butane-2,3-dione monoximate (Ox-) in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C. The Hammett plot for the reactions of 7a-7e consists of two intersecting straight lines while the Yukawa-Tsuno plot exhibits an excellent linearity with ρX = 0.85 and r = 0.58, indicating that the nonlinear Hammett plot is not due to a change in the rate-determining step but is caused by resonance stabilization of the ground state (GS) of the substrate possessing an electron-donating group (EDG). The Bronsted-type plot for the reactions of Y-substituted-phenyl cinnamates (8a-8e) is linear with βlg = - 0.64, which is typical of reactions reported previously to proceed through a concerted mechanism. The a-nucleophile (Ox-) is more reactive than the reference normalnucleophile (4-ClPhO-). The magnitude of the α-effect (i.e., the kOx-/k4-ClPhO- ratio) is independent of the electronic nature of the substituent X in the nonleaving group but increases linearly as the substituent Y in the leaving group becomes a weaker electron-withdrawing group (EWG). It has been concluded that the difference in solvation energy between Ox- and 4-ClPhO - (i.e., GS effect) is not solely responsible for the α-effect but stabilization of transition state (TS) through a cyclic TS structure contributes also to the Y-dependent a-effect trend (i.e., TS effect).

Selective synthesis of 3,4-dihydrocoumarins and chalcones from substituted aryl cinnamic esters

Coumarins are ubiquitous in plant kingdom and have been used as antitumor, antifungals, anticoagulants, insecticides. Chalcones are also widespread in plant kingdom and have been known to possess diverse biological activities; antibacterial, antifungal, antitumor and anti-inflammatory, etc. As they are considered as important natural products, numerous synthetic approaches have been reported up to the present. We devise a new selective method of preparing dihydrocoumarins and chalcones from aryl cinnamates by the selection of reagents. Dihydrocoumarin derivatives were prepared selectively by using intramolecular cyclization catalyzed by p-toluene sulfonic acid. Also, chalcones were prepared by Fries-rearrangement catalyzed by TiCl4. This method can be used for preparing various coumarin & chalcone compounds.

Synthesis and antimicrobial screening of cyclohexenones and oxazines

4-Cinnamoyloxybenzylidene (I) on condensation with various ketones yielded 1-aryl-3-(4′-cinnamoyloxyphenyl)-2-propene-1-ones (2), which on cyclization with ethyl accetoacetate in acetone and urea in alcoholic KOH furnished 6-carbethoxy-5-(4′-cinnamoyloxyp