81069-40-1

Upstream product

• 140-88-5 ethyl acrylate 
• 5538-51-2 O-acetylsalicyloyl chloride 
• 3943-94-0 (E)-ethyl 2-hydroxycinnamate 
• 108-24-7 acetic anhydride 
• 90-02-8 salicylaldehyde 
• 35922-87-3 acetic acid trans-2-(1-propenyl)phenyl ester 

Downstream Products

• 20921-04-4 ethyl 3-(2-hydroxyphenyl)propanoate 

Relevant academic research and scientific papers

Trans-cinnamic acid ester compound and its synthetic method and application

The invention relates to a trans cinnamic acid ester compound, as well as a synthetic method and application thereof. At present, a typic miticide has the growing problems, such as drug resistance and environment and ecology, so that a new animal miticide needs to be developed very urgently. The trans cinnamic acid ester compound has the molecular structure shown in the specification, wherein R refers to alkyl radical, R1 and R2 refer to hydrogen, hydroxide radical, alkyl radical, alkoxy, fatty acyloxy, halogen, methylenedioxy or nitro, and are the same or different; the trans cinnamic acid ester compound can be used for preparing miticides for animals and people. The compound serves as a novel miticide, is relatively low in toxicity, small in molecular weight, few in synthetic steps, simple to operate, low in production cost, and suitable for large-scale industrial production; the acaricidal activity is remarkably stronger that of a miticide applied in current all clinics.

Ethyl cinnamate derivatives as promising high-efficient acaricides against Psoroptes cuniculi: Synthesis, bioactivity and structure-activity relationship

This paper reported the synthesis, structure-activity relationship (SAR) and acaricidal activity in vitro against Psoroptes cuniculi, a mange mite, of 25 ethyl cinnamate derivatives. All target compounds were synthesized and elucidated by means of MS, 1H- and 13C-NMR analysis. The results showed that 24 out of 25 tested compounds at 1.0 mg/mL demonstrated acaricidal activity in varying degrees. Among them, 6, 15, 26, 27 and 30 showed significant activity with median lethal concentration values (LC50) of 89.3, 119.0, 39.2, 29.8 and 41.2 μg/mL, respectively, which were 2.1- to 8.3-fold the activity of ivermectin (LC50=247.4 μg/mL), a standard drug in the treatment of Psoroptes cuniculi. Compared with ivermectin, with a median lethal time value (LT50) of 8.9 h, 27 and 30 showed smaller LTM50 values of 7.9 and 1.3 h, respectively, whereas 6, 15 and 26 showed slightly larger LT50 values of 10.6, 11.0 and 10.4 h at 4.5 μmol/mL. SARs showed that the presence of o-NO2 or m-NO2 on the benzene ring significantly improved the activity, whereas the introduction of a hydroxy, methoxy, acetoxy, methylenedioxy, bromo or chloro group reduced the activity. (E)-Cinnamates were more effective than their (Z)-isomer. Nevertheless, the carbon-carbon double bond in the acrylic ester moiety was proven not to be essential to improve the activity of cinnamic acid esters. Thus, the results strongly indicate that cinnamate derivatives, especially their dihydro derivatives, should be promising candidates or lead compounds for the development of novel acaricides for the effective control of animal or human acariasis.

A general model for selectivity in olefin cross metathesis

In recent years, olefin cross metathesis (CM) has emerged as a powerful and convenient synthetic technique in organic chemistry; however, as a general synthetic method, CM has been limited by the lack of predictability in product selectivity and stereoselectivity. Investigations into olefin cross metathesis with several classes of olefins, including substituted and functionalized styrenes, secondary allylic alcohols, tertiary allylic alcohols, and olefins with α-quaternary centers, have led to a general model useful for the prediction of product selectivity and stereoselectivity in cross metathesis. As a general ranking of olefin reactivity in CM, olefins can be categorized by their relative abilities to undergo homodimerization via cross metathesis and the susceptibility of their homodimers toward secondary metathesis reactions. When an olefin of high reactivity is reacted with an olefin of lower reactivity (sterically bulky, electron-deficient, etc.), selective cross metathesis can be achieved using feedstock stoichiometries as low as 1:1. By employing a metathesis catalyst with the appropriate activity, selective cross metathesis reactions can be achieved with a wide variety of electron-rich, electron-deficient, and sterically bulky olefins. Application of this model has allowed for the prediction and development of selective cross metathesis reactions, culminating in unprecedented three-component intermolecular cross metathesis reactions.

Ruthenium-catalyzed olefin cross metathesis of styrenes as an alternative to the Heck and cross-coupling reactions

The use of olefin cross metathesis as a method for the formation of styrenyl-olefins is described using allylic substituted olefins and electron-deficient olefins. These methods provide an orthogonal method to alternative olefination strategies, such as the Heck reaction. These methods have also been employed in the total synthesis of 3-flavanols.

Process for the preparation of alkenylbenzenecarboxylic acid derivatives and alkenylnaphthalenecarboxylic acid derivatives

Compounds of the formula I STR1 in which p, m, Z, R, R' and Y are as defined in claim 1, can be obtained in a simple and economical manner by a novel process which comprises reacting a halide of the formula STR2 with the corresponding acrylic acid derivative, in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I), and functional derivatives prepared therefrom, are useful for the preparation of photocrosslinkable polymers, which can in particular be employed as (so-called) photoresists.

THE PALLADIUM-CATALYSED ARYLATION OF ACTIVATED ALKENES WITH AROYL CHLORIDES

Aroyl chlorides react with activated alkenes in presence of a tertiary amine and a catalytic amount of palladium acetate to give arylated alkenes, specifically cinnamic acid derivatives and stilbenes.The reaction involves a highly efficient decarbonylation of the aroyl chloride.High yields can be obtained at low catalyst concentration by choice of an appropriate base.The reaction is not particularly sensitive to substituents in the aroyl chloride, although strongly electron-donating groups are advantagenous (yields up to 98percent).With monosubstituted alkenes E-isomers are formed with almost complete specificity.A mechanism for the reaction is proposed.