357155-86-3

Basic information

• Product Name: methyl 4-[(1E)-3-(4-methoxyphenyl)-3-oxoprop-1-en-1-yl]benzoate
• Synonyms: benzoic acid, 4-[(1E)-3-(4-methoxyphenyl)-3-oxo-1-propen-1-yl]-, methyl ester
• CAS NO: 357155-86-3
• Molecular Formula: C₁₈H₁₆O₄
• Molecular Weight: 296.3172
• Mol File: 357155-86-3.mol

Chemical Properties

• Boiling Point: 471.7°C at 760 mmHg
• Flash Point: 209.3°C
• Density: 1.177g/cm³
• Vapor Pressure: 4.55E-09mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: methyl 4-[(1E)-3-(4-methoxyphenyl)-3-oxoprop-1-en-1-yl]benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-[(1E)-3-(4-methoxyphenyl)-3-oxoprop-1-en-1-yl]benzoate(357155-86-3)
• EPA Substance Registry System: methyl 4-[(1E)-3-(4-methoxyphenyl)-3-oxoprop-1-en-1-yl]benzoate(357155-86-3)

Safety Data

• Hazardous Substances Data: 357155-86-3(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 106315-53-1 4-[3-(4-methoxyphenyl)-3-oxo-propenyl]benzoic acid 
• 20912-79-2 4-methoxyphenacylidene dimethylsulphurane 
• 125587-45-3 methyl 4-[(2-tosylhydrazono)methyl]benzoate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 1571-08-0 methyl 4-formylbenzoate 

Relevant articles and documents

Alkene Synthesis by Photo-Wolff-Kischner Reaction of Sulfur Ylides and N-Tosylhydrazones

A visible-light-driven and room temperature photo-Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones has been developed for the first time to provide modular access to alkene synthesis. The high functional group tolerance and broad substrate scope were demonstrated by more than 60 examples. Both E- and Z-olefinic stereochemistry in the products could be controlled with excellent stereoselectivity. A series of mechanistic studies support that the reaction should proceed through a radical-carbanion crossover pathway, specifically involving addition of photo-generated sulfur ylide radical cations to N-tosylhydrazones to form carbanions and subsequent Wolff-Kischner process.

Chalcone-Supported Cardiac Mesoderm Induction in Human Pluripotent Stem Cells for Heart Muscle Engineering

Human pluripotent stem cells (hPSCs) hold great promise for applications in cell therapy and drug screening in the cardiovascular field. Bone morphogenetic protein 4 (BMP4) is key for early cardiac mesoderm induction in hPSC and subsequent cardiomyocyte derivation. Small-molecular BMP4 mimetics may help to standardize cardiomyocyte derivation from hPSCs. Based on observations that chalcones can stimulate BMP4 signaling pathways, we hypothesized their utility in cardiac mesoderm induction. To test this, we set up a two-tiered screening strategy, (1) for directed differentiation of hPSCs with commercially available chalcones (4’-hydroxychalcone [4’HC] and Isoliquiritigen) and 24 newly synthesized chalcone derivatives, and (2) a functional screen to assess the propensity of the obtained cardiomyocytes to self-organize into contractile engineered human myocardium (EHM). We identified 4’HC, 4-fluoro-4’-methoxychalcone, and 4-fluoro-4’-hydroxychalcone as similarly effective in cardiac mesoderm induction, but only 4’HC as an effective replacement for BMP4 in the derivation of contractile EHM-forming cardiomyocytes.

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.

Solid-supported cross-metathesis and a formal alkane metathesis for the generation of biologically relevant molecules

Solid-phase synthetic strategies toward the generation of libraries of biologically relevant molecules were developed using olefin cross-metathesis as a key step. It is remarkably the formal alkane metathesis based on a one-pot, microwave-assisted, ruthenium-catalyzed cross-metathesis and reduction to obtain Csp3-Csp3 linkages.