99429-99-9

Upstream product

• 106-44-5 p-cresol 
• 102-92-1 cinnamoyl chloride 
• 621-82-9 Cinnamic acid 
• 5720-05-8 4-methylphenylboronic acid 
• 18736-43-1 4-nitro-phenyl cinnamate 
• 112404-04-3 O-methyl cinnamohydroxamate 
• 140-10-3 (E)-3-phenylacrylic acid 
• 21947-71-7 cinnamic anhydride 
• 14643-62-0 tris(p-methylphenyl) borate 
• 14371-10-9 (E)-3-phenylpropenal 
• 775-12-2 diphenylsilane 
• 102-92-1 Cinnamoyl chloride 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 

Downstream Products

• 4714-21-0 E-1-methyl-4-styryl-benzene 
• 124-38-9 carbon dioxide 
• 4714-21-0 4-methylstilbene 
• 1775-98-0 2'-hydroxy-5'-methylchalcone 
• 40546-94-9 6-methyl-4-phenyl-3,4-dihydrocoumarin 
• 1775-98-0 (E)-1-(2-hydroxy-5-methylphenyl)-3-phenylprop-2-en-1-one 
• 109089-77-2 3-(2-methoxy-5-methyl-phenyl)-3-phenyl-propionic acid 
• 16299-22-2 6-methyl-4-phenylchromen-2-one 
• 3489-11-0 6-methylflavanone 

Relevant academic research and scientific papers

The design and synthesis of transient receptor potential vanilloid 3 inhibitors with novel skeleton

Transient receptor potential vanilloid 3 (TRPV3) channel as a member of thermo TRPV subfamily is primarily expressed in the keratinocytes of the skin and sensory neurons, and plays critical roles in various physiological and pathological processes such as

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.

Electrodimerization of N-Alkoxyamides for Zinc(II) Catalyzed Phenolic Ester Synthesis under Mild Reaction Conditions

An electrochemical On-Off method for phenolic ester synthesis from N-alkoxyamides has been reported. This one-pot protocol begins with rapid and selective electrodimerization of the amide using n-Bu4NI (TBAI) as an electrocatalyst. The reaction proceeds further in the absence of current via Zn catalyzed C?N bond activation of the amide dimer followed by its coupling with phenol to form the ester. The present methodology is ligand-free and takes place under mild reaction conditions. This transformation incorporates a wide variety of phenols and amide substrates leading to the formation of functionalized esters highlighting its versatility. (Figure presented.).

Preparation method for synthesis of phenolic ester through thiocarboxylic acid mediated visible light catalyzed phenol acylation reaction

The invention discloses a preparation method for synthesis of phenolic ester through a thiocarboxylic acid mediated visible light catalyzed phenol acylation reaction. Thiocarboxylic acid compounds andphenol compounds are subjected to a site specific reaction under certain conditions to produce phenolic ester compounds, wherein the certain conditions are as follows: under the conditions of normaltemperature, normal pressure and visible light, K2CO3 is used as an alkaline catalyst, terpyridyl ruthenium dichloride hexahydrate is used as a photosensitizer and acetonitrile is used as a reaction solvent. Synthesis of phenolic ester under catalysis of visible light is realized, thiocarboxylic acid is used as an acylation reagent, and the site specific phenol esterification reaction is realizedefficiently under mild conditions of normal temperature, normal pressure and visible light. The method has mild reaction conditions, large substrate functional group tolerance, high applicability andhigh yield, and an efficient, reliable and economical preparation method is provided for synthesis of phenolic ester.

Diacyl Disulfide: A Reagent for Chemoselective Acylation of Phenols Enabled by 4-(N,N-Dimethylamino)pyridine Catalysis

A general and excellent acylation reagent, diacyl disulfide, was uncovered for efficient ester formation enabled by DMAP (4-(N,N-dimethylamino)pyridine) catalysis. This protocol offered a promising synthetic platform on site-selective acylation of phenolic and primary aliphatic hydroxyl groups, which greatly expanded the realm of protecting group chemistry. The importance of the reagent was also reflected by its excellent moisture tolerance, high efficiency, and potential in synthetic chemistry and biologically meaningful natural product modification.

N-heterocyclic carbenes: IX. Oxidative esterification of aromatic aldehydes with arylboronic acids catalyzed by N-heterocyclic carbenes

Aromatic aldehydes reacted with arylboronic acids under catalysis by N-heterocyclic carbene and oxic conditions to produce phenol esters.

Influence of electronically and sterically tunable cinnamate ligands on the spectroscopic properties and reactivity of bis(triphenylphosphine)platinum(0) olefin complexes

A total of 48 new bis(triphenylphosphine)(cinnamic acid ester)platinum(0) complexes were synthesized to examine electronic and steric influences on their behavior as inhibited precatalysts and to correlate this with 1H, 13C, 19F, 31P and 195Pt NMR spectroscopic, IR spectroscopic, and X-ray structural properties (9 X-ray structures included). The substituent at the 4-position of the phenyl group proved to be a valuable moiety in controlling the electronic properties of the olefin ligand and, therefore, the metal-ligand bond strength. Reactivity and NMR spectroscopic data correlate with the Hammett parameters of this substituent: in particular, the coupling constants 2JPP and 1JPPt. The reactivity of the complexes was determined via NMR titration with triphenylphosphine (1H NMR; triggering ligand substitution) and reaction with diphenylsilane (1H and 29Si NMR; triggering oxidative addition). The determined equilibria correlate with the electron density of the olefin. As one quintessence the reactivity can be predicted indirectly from the NMR 2JPP coupling constants of the complexes, as was also found for the related Pd complexes.

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.

A convenient solid-phase synthesis of coumarins by TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes

TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succinimidyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocou

Influence of electronically and sterically tunable cinnamate ligands on the spectroscopic, kinetic, and thermodynamic properties of bis(triphenylphosphine) palladium(0) olefin complexes

A detailed study of the influence of electronic and steric characteristics of cinnamic acid esters on the spectroscopic, kinetic, and thermodynamic properties of bis(triphenylphosphine)palladium(0) cinnamic acid ester complexes is presented (51 different new complexes included). These complexes show a dynamic behavior on the NMR spectroscopic time scale. Therefore, the rotational barriers of the olefin about the metalolefin bond as well as the dissociation entropy and enthalpy of the olefin and the dissociation mechanism could be determined. These findings are interpreted together with the NMR spectroscopic, IR spectroscopic, and X-ray structural data (7 new structures included) concerning the influence of the different olefin ligands on the complex properties by means of Hammett plots. DFT calculations were performed to support the mechanistic conclusions.