39626-31-8

Basic information

• Product Name: (Z)-ethyl 2-benzoyl-3-phenylacrylate
• Synonyms: (Z)-ethyl 2-benzoyl-3-phenylacrylate
• CAS NO: 39626-31-8
• Molecular Formula: C₁₈H₁₆O₃
• Molecular Weight: 280.31784
• Mol File: 39626-31-8.mol
• Article Data: 22

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (Z)-ethyl 2-benzoyl-3-phenylacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-ethyl 2-benzoyl-3-phenylacrylate(39626-31-8)
• EPA Substance Registry System: (Z)-ethyl 2-benzoyl-3-phenylacrylate(39626-31-8)

Safety Data

• Hazardous Substances Data: 39626-31-8(Hazardous Substances Data)

Usage

Description

(Z)-ethyl 2-benzoyl-3-phenylacrylate, with the molecular formula C19H16O3, is a clear, colorless liquid characterized by a molecular weight of 292.33 g/mol. This chemical compound is recognized for its potential as a building block in the synthesis of biologically active molecules, making it a valuable asset in organic synthesis and pharmaceutical research.

Uses

Used in Organic Synthesis:
(Z)-ethyl 2-benzoyl-3-phenylacrylate is used as a key intermediate for the creation of various biologically active molecules, contributing to the advancement of pharmaceutical research and development.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (Z)-ethyl 2-benzoyl-3-phenylacrylate is utilized as a building block for the synthesis of novel drugs, potentially leading to the discovery of new treatments for various medical conditions.
Used in the Production of Fine Chemicals:
(Z)-ethyl 2-benzoyl-3-phenylacrylate is also employed in the manufacturing process of fine chemicals, which are essential in various industries, including pharmaceuticals, agriculture, and materials science.
Used as an Anti-Inflammatory Agent:
(Z)-ethyl 2-benzoyl-3-phenylacrylate has demonstrated potential as an anti-inflammatory agent and is being studied for its possible application in topical formulations to treat skin diseases.
Safety Precautions:
It is crucial to handle (Z)-ethyl 2-benzoyl-3-phenylacrylate with care, as it may pose risks if ingested, inhaled, or comes into contact with the skin. To ensure safety, this compound should be stored in a cool, dry place, away from direct sunlight.

Upstream product

• 98-88-4 benzoyl chloride 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 64967-44-8 (Z)-ethyl 3-acetyloxy-3-phenyl-2-propenoate 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 3376-25-8 (Z)-N-benzylidenecyclohexanamine oxide 
• 3376-23-6 C-phenyl-N-methylnitrone 
• 148345-11-3 2-cyclohexyl-4-ethoxycarbonyl-3,5-diphenyl-4-isoxazoline 
• 74-88-4 methyl iodide 
• 148345-10-2 2-methyl-4-ethoxycarbonyl-3,5-diphenyl-4-isoxazoline 
• 538-74-9 dibenzyl sulfide 
• 831-91-4 Benzyl phenyl sulfide 
• 766-92-7 [(methylthio)methyl]-benzene 

Downstream Products

• 95956-92-6 2-hydroxy-6-methyl-2,4-diphenyl-1,2,3,4-tetrahydro-pyridine-3,5-dicarboxylic acid diethyl ester 
• 93-89-0 benzoic acid ethyl ester 
• 1129303-30-5 C₁₈H₁₈O₃ 
• 116471-58-0 4,5-dihydro 2,4-diphenyl 5-ethyl 3-ethoxycarbonyl 5-methylfuran 
• 116471-58-0 4,5-dihydro 2,4-diphenyl 5-ethyl 3-ethoxycarbonyl 5-methylfuran 
• 116471-50-2 4,5-dihydro 5,5-dimethyl 2,4-diphenyl 3-ethoxycarbonylfuran 
• 56409-75-7 ethyl 2-benzyl-3-oxo-3-phenylpropanoate 
• 105199-60-8 4,6-Diphenyl-5-ethoxycarbonyl-3-cyanopyridine-2(1H)thione 

Relevant articles and documents

Substituent-Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and Oxa-Bridged Fused Heterocycles

Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the high chemoselectivity. These provide a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles. (Figure presented.).

Enzyme Promiscuity as a Remedy for the Common Problems with Knoevenagel Condensation

A new protocol based on lipase-catalyzed tandem reaction toward α,β-enones/enoesters is presented. For the synthesis of the desired products the tandem process based on enzyme-catalyzed hydrolysis and Knoevenagel reaction starting from enol acetates and aldehyde is developed. The relevant impact of the reaction conditions including organic solvent, enzyme type, and temperature on the course of the reaction was revealed. It was shown that controllable release of the active methylene compound from the corresponding enol carboxylate ensured by enzymatic reaction diminishes significantly the formation of the unwanted co-products. Furthermore, this protocol was extended by including a second tandem chemoenzymatic transformation engaging various aldehyde precursors. After a careful optimization of the reaction conditions, the target products were obtained with yields up to 86 % and with excellent E/Z-selectivity.

CBr4 as a Halogen Bond Donor Catalyst for the Selective Activation of Benzaldehydes to Synthesize α,β-Unsaturated Ketones

CBr4 has been employed as a halogen bond donor catalyst for the selective activation of aldehyde, to achieve an efficient solvent- and metal-free CC bond forming reaction in the presence of strong acid sensitive groups such as methoxy, cyanide, ester, and ketal for the synthesis of α,β-unsaturated ketones. This unique capability of CBr4 to act as a halogen bond donor has been explored and established using UV-vis as well as IR spectroscopy. Moreover, this unprecedented methodology enables the synthesis of the pharmaceutically important molecule licochalcone A.