6236-62-0

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL TRANS 2-HYDROXYCINNAMATE 97 is used as an intermediate compound for the synthesis of 4-phenyl-2H-chromen-2-one, a 4-aryl coumarin derivative. This derivative is significant in the pharmaceutical industry due to its potential applications in drug development and therapeutics.
Used in Chemical Synthesis:
ETHYL TRANS 2-HYDROXYCINNAMATE 97 is used as a key building block in the chemical synthesis of various organic compounds. Its unique structure allows it to be a valuable component in creating a wide range of molecules with different applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
ETHYL TRANS 2-HYDROXYCINNAMATE 97 is used as a research compound for studying its properties and potential applications in different fields. Its unique structure and reactivity make it an interesting subject for scientific investigations, which could lead to the discovery of new applications and uses for ETHYL TRANS 2-HYDROXYCINNAMATE 97.

InChI:InChI=1/C11H12O3/c1-2-14-11(13)8-7-9-5-3-4-6-10(9)12/h3-8,12H,2H2,1H3/b8-7+

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 90-02-8 salicylaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 
• 78-39-7 Triethyl orthoacetate 
• 1530-45-6 (carbethoxymethyl)triphenylphosphonium bromide 
• 140-88-5 ethyl acrylate 
• 108-95-2 phenol 
• 614-60-8 o-Coumaric acid 
• 64-17-5 ethanol 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 86832-85-1 diethyl c-3,c-4-bis(2-hydroxyphenyl)cyclobutane-r-1,c-2-dicarboxylate 
• 16139-79-0 ethyl diphenylphosphonoacetate 
• 5663-67-2 2-acetoxybenzaldehyde 
• 623-73-4 diazoacetic acid ethyl ester 

Downstream Products

• 91-64-5 coumarin 
• 20921-04-4 ethyl 3-(2-hydroxyphenyl)propanoate 
• 3199-61-9 ethyl coumarilate 
• 100008-86-4 o-(β-ethoxycarbonylvinyl)phenyl N-phenylbenzohydrazidate 
• 194031-13-5 2,2-Dimethyl-malonic acid 2-((E)-2-ethoxycarbonyl-vinyl)-phenyl ester methyl ester 
• 51764-86-4 2-hydroxycinnamyl alcohol 
• 70326-80-6 ethyl (E)-3-(2-ethoxyphenyl)propionate 
• 949448-93-5 2-(β-ethoxycarbonyl)styrenyl allenoate 
• 15185-05-4 4-phenylcoumarin 
• 1415475-15-8 4-(3,4,5-trimethoxyphenyl)-2H-chromen-2-one 

Relevant academic research and scientific papers

Coumarins by Direct Annulation: β-Borylacrylates as Ambiphilic C3-Synthons

Modular β-borylacrylates have been validated as programmable, ambiphilic C3-synthons in the cascade annulation of 2-halo-phenol derivatives to generate structurally and electronically diverse coumarins. Key to this [3+3] disconnection is the BPin unit which serves a dual purpose as both a traceless linker for C(sp2)–C(sp2) coupling, and as a chromophore extension to enable inversion of the alkene geometry via selective energy transfer catalysis. Mild isomerisation is a pre-condition to access 3-substituted coumarins and provides a handle for divergence. The method is showcased in the synthesis of representative natural products that contain this venerable chemotype. Facile entry into π-expanded estrone derivatives modified at the A-ring is disclosed to demonstrate the potential of the method in bioassay development or in drug repurposing.

Free radical scavenging and α-glucosidase inhibitory activity of (E)-methyl/ethyl-3-(2-hydroxyphenyl)acrylates

(E)-Methyl/ethyl-3-(2-hydroxyphenyl)acrylates 3a-x have been prepared by the reaction of salicylaldehydes 1a-l with Wittig reagents such as methyl (triphenylphosphoranylidene)acetate 2a and ethyl (triphenylphosphoranylidene)acetate 2b in dry DCM at room t

Visible-Light-Induced C(sp2)-C(sp3) Coupling Reaction for the Regioselective Synthesis of 3-Functionalized Coumarins

A photocatalysis strategy for the regioselective synthesis of 3-functionalized coumarins is reported. With visible light irradiation, a direct and regioselective C(sp2)-C(sp3) coupling reaction of 3-(2-hydroxyphenyl)acrylates with ethers or thioethers occurs by using Ru(bpy)3Cl2·6H2O as a photocatalyst and TBHP as an oxidant. The cascade process involves alkenylation of the C(sp3)-H bond of ethers and lactonization, furnishing 3-alkylated coumarins as the final products. This approach is characterized by a broad substrate scope, mild reaction conditions, and simplified operation. The synthesis of 3-alkylated coumarins could be realized by a one-pot procedure, starting from commercially available salicylaldehyde.

Platinum complex containing diphosphine meta-position carborane ligand and preparation method and application of platinum complex

The invention relates to a platinum complex containing a diphosphine m-carborane ligand and a preparation method and application of the platinum complex, the method of the platinum complex comprises the following steps: reacting n-BuLi with m-carborane m-

Ruthenium-catalyzed intramolecular arene C(sp2)-H amidation for synthesis of 3,4-dihydroquinolin-2(1 H)-ones

We report the [Ru(p-cymene)(l-proline)Cl] ([Ru1])-catalyzed cyclization of 1,4,2-dioxazol-5-ones to form dihydroquinoline-2-ones in excellent yields with excellent regioselectivity via a formal intramolecular arene C(sp2)-H amidation. The reactions of the 2- and 4-substituted aryl dioxazolones proceeds initially through spirolactamization via electrophilic amidation at the arene site, which is para or ortho to the substituent. A Hammett correlation study showed that the spirolactamization is likely to occur by electrophilic nitrenoid attack at the arene, which is characterized by a negative ρ value of -0.73.

Cascade Synthesis of 4-Arylcoumarins: Pd-Catalyzed Arylations and Cyclizations with (E)-Ethyl 3-(2-Hydroxyaryl)acrylates and Triarylantimony Difluorides

Herein, we describe a simple general method for the synthesis of 4-arylcoumarins using pentavalent organoantimony compounds. The reactions of 3-(2-hydroxyaryl)acrylates with triarylantimony difluorides in the presence of Pd(OAc)2 (10 mol-%) and 2,2'-bipyridyl (10 mol-%) at 80 °C under aerobic conditions afforded 4-arylcoumarins in good-to-excellent yields. This protocol involves a cascade oxidative Heck-type arylation followed by cyclization, with all the aryl groups in the triarylantimony difluoride transferred to the coupling products. Triarylantimony difluorides resulted in better outcomes than those obtained with other pentavalent organoantimony or bismuth compounds.

Late-Stage Direct o-Alkenylation of Phenols by PdII-Catalyzed C?H Functionalization

o-Alkenylation of unprotected phenols has been developed by direct C?H functionalization catalyzed by PdII. This work features phenol group as a directing group and realizes highly site-selective C?H bond functionalization of phenols to achieve the corresponding products in moderate to excellent yields at 60 °C. The advantages of this reaction include unprecedented C?H functionalization using phenol as a directing group, high regioselectivity, good substrate scope, mild reaction conditions, and high efficiency. To the best of our knowledge, this is the first example of a regioselective C?H alkenylation of unprotected phenols utilizing phenolic hydroxyl group as a directing group. The alkenylation of unprotected tyrosine and intramolecular cyclization are also successfully carried out under this catalytic system in good yields. Furthermore, this novel method enables a late-stage modification of complex phenol-containing bioactive molecules toward a diversity-oriented drug discovery.

Rh-Catalyzed Deformylative Coupling of Salicylaldehydes with Acrylates and Acrylamides

An unprecedented deformylative coupling of salicylaldehydes to acrylates and acrylamides under Rh-catalyzed conditions is reported. These deformylative couplings afforded o-hydroxycinnamates and o-hydroxycinnamamides with broad functional group tolerance and high chemoselectivity under milder reaction conditions.

Phenol compound ortho-position direct olefination method and olefinated phenol compound

The invention relates to a phenol compound ortho-position direct olefination method and an olefinated phenol compound prepared with the method. The method comprises the steps that a phenol compound shown by the formula (II) and an olefin compound shown by

Palladium catalyzed Heck-arylation/cyclization cascade: An environmentally benign and efficient synthesis of 4-arylcoumarins in water

An environmentally benign and efficient approach for the synthesis of 4-arylcoumarins from ortho-hydroxy cinnamate ester derivatives with aryl iodides was developed in water under aerobic conditions. This transformation proceeds through a palladium catalyzed Heck-arylation/cyclization cascade reaction. The present protocol features a wide substrate scope and readily available starting materials to afford the desired products in high to excellent yields.