351-46-2

Usage

InChI:InChI=1/C11H11FO2/c1-2-14-11(13)7-6-9-4-3-5-10(12)8-9/h3-8H,2H2,1H3

Upstream product

• 20595-30-6 3-fluorocinnamic acid 
• 64-17-5 ethanol 
• 39098-87-8 3-fluoro-cinnamoyl chloride 
• 462-06-6 fluorobenzene 
• 140-88-5 ethyl acrylate 
• 20595-30-6 3-Fluorocinnamic acid 
• 456-48-4 3-Fluorobenzaldehyde 
• 1121-86-4 1-Fluoro-3-iodobenzene 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 1073-06-9 3-fluorobromobenzene 
• 1664-56-8 m-aminocinnamic acid 

Downstream Products

• 7116-37-2 ethyl 3-(3-fluorophenyl)propanoate 
• 1019650-86-2 ethyl 3-(3-fluorophenyl)-4-nitrobutanoate 
• 854141-65-4 4-(3-fluoro-phenyl)-1-hydroxymethyl-pyrrolidin-2-one 
• 227616-82-2 (S)-3-[Benzyl-((R)-1-phenyl-ethyl)-amino]-3-(3-fluoro-phenyl)-propionic acid ethyl ester 
• 125872-67-5 (E)-3-(3-fluorophenyl)prop-2-en-1-ol 
• 1361214-45-0 (R)-tert-butyl 3-((2R,3S)-2-((E)-3-fluorostyryl)-4-oxo-3-((S)-2-oxo-4-phenyloxazolidin-3-yl)azetidin-1-yl)-4-oxo-4-(((R)-1-phenylethyl)amino)butanoate 
• 1361214-48-3 (R)-3-((2R,3S)-2-((E)-3-fluorostyryl)-4-oxo-3-((S)-2-oxo-4-phenyloxazolidin-3-yl)azetidin-1-yl)-4-oxo-4-(((R)-1-phenylethyl)amino)butanoic acid 
• 1361214-50-7 (R)-4-([1,4'-bipiperidin]-1'-yl)-2-((2R,3S)-2-((E)-3-fluorostyryl)-4-oxo-3-((S)-2-oxo-4-phenyloxazolidin-3-yl)azetidin-1-yl)-4-oxo-N-((R)-1-phenylethyl)butanamide 
• 20595-30-6 3-Fluorocinnamic acid 
• 1197397-25-3 (Z)-3-(3-fluorophenyl)prop-2-en-1-ol 
• 915939-64-9 tert-butyl (E)-3-(3'-fluorophenyl)prop-2-en-1-yl carbonate 
• 26905-44-2 3-(3-fluorophenyl)-2-propen-1-ol 

Relevant academic research and scientific papers

Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites

The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had

Solvent role in the lipase-catalysed esterification of cinnamic acid and derivatives. Optimisation of the biotransformation conditions

The esterification of cinnamic acid has been deeply investigated using ethanol as nucleophile and Candida antarctica lipase type B (CAL-B) as suitable biocatalyst. Special attention has been paid to the role that the solvent plays in the production of ethyl cinnamate. Therefore, volatile organic solvents and deep eutectic mixtures were employed in order to find optimal reaction conditions. Once that hexane was selected as the solvent of choice, other parameters that affect the enzyme activity were investigated in order to produce ethyl cinnamate with excellent yield. The CAL-B loading, nucleophile equivalents, temperature and reaction time have been identified as key parameters in the enzyme efficiency, and the potential of lipase-catalysed esterification has been finally exploited to produce a series of ethyl esters with different pattern substitutions on the aromatic ring.

Selective Synthesis of Z-Cinnamyl Ethers and Cinnamyl Alcohols through Visible Light-Promoted Photocatalytic E to Z Isomerization

A photocatalytic E to Z isomerization of alkenes using an iridium photosensitizer under mild reaction conditions is disclosed. This method provides scalable and efficient access to Z-cinnamyl ether and allylic alcohol derivatives in high yields with excellent stereoselectivity. Importantly, this method also provides a powerful strategy for the selective synthesis of Z-magnolol and honokiol derivatives possessing potential biological activity.

Meta -Selective C-H functionalisation of aryl boronic acids directed by a MIDA-derived boronate ester

N-Methyliminodiacetic acid (MIDA) boronates are boronic acid derivatives which are stable to reduction, oxidation and transmetalation. This has led to their widespread use as boronic acid protecting groups (PGs) and in iterative cross-couplings. We describe herein the development of a novel MIDA derivative that acts in a dual manner, as a protecting group and a directing group (DG) for meta C(sp2)-H functionalisation of arylboronic acids. Palladium catalysed C-H alkenylations, acetoxylations and arylations are possible, at room temperature and under aerobic conditions. Deprotection to reveal the functionalised boronic acids is rapid and allows for full recovery of the DG. The technique allows the facile diversification of aryl boronic acids and their subsequent use in a range of reactions or in iterative processes.

Synthesis and Preclinical Evaluation of an 18F-Labeled Synaptic Vesicle Glycoprotein 2A PET Imaging Probe: [18F]SynVesT-2

Synaptic vesicle glycoprotein 2A (SV2A) is a 12-pass transmembrane glycoprotein ubiquitously expressed in presynaptic vesicles. In vivo imaging of SV2A using PET has potential applications in the diagnosis and prognosis of a variety of neuropsychiatric diseases, e.g., Alzheimer's disease, Parkinson's disease, schizophrenia, multiple sclerosis, autism, epilepsy, stroke, traumatic brain injury, post-traumatic stress disorder, depression, etc. Herein, we report the synthesis and evaluation of a new 18F-labeled SV2A PET imaging probe, [18F]SynVesT-2, which possesses fast in vivo binding kinetics and high specific binding signals in non-human primate brain.

Rh(III)-Catalyzed Enaminone-Directed C-H Coupling with α-Diazo-α-phosphonoacetate for Reactivity Discovery: Fluoride-Mediated Dephosphonation for C-C Coupling Reactions

Rh(III)-catalyzed enaminone-directed C-H coupling with α-diazo-α-phosphonoacetate has been used for the identification of fluoride-mediated dephosphonation C-C coupling reactivity for the synthesis of 4-hydroxy-1-naphthoates. Intermolecular C-C coupling of α-phosphonoacetate and benzaldehyde for (E)-selective α,β-unsaturated ester synthesis has also been achieved.

Synthesis of 5,6-dehydrokawain and some fluorinated analogues

An efficient methodology for the synthesis of 6-styrenylpyrone in a four-step sequence is reported. The reactions were performed under catalyst-free conditions with mild and affordable reagents to produce 5,6-dehydrokawain and fluorinated derivatives in good to excellent overall yields (72–86%) on a multigram scale. Two novel difluorinated derivatives are reported here for the first time.

5,6-dihydropyrrolo[2,1-a]isoquinolines as alternative of new drugs with cytotoxic activity

In this study, the pyrrolo[2,1-a]isoquinolines 4a–n were synthesized in good yields in a three steps synthesis from the corresponding α,β-unsaturated esters starting materials. These compounds were tested on six human cancer cells lines to measure the cyt

Ligand-accelerated non-directed C-H functionalization of arenes

The directed activation of carbon-hydrogen bonds (C-H) is important in the development of synthetically useful reactions, owing to the proximity-induced reactivity and selectivity that is enabled by coordinating functional groups. Palladium-catalysed non-directed C-H activation could potentially enable further useful reactions, because it can reach more distant sites and be applied to substrates that do not contain appropriate directing groups; however, its development has faced substantial challenges associated with the lack of sufficiently active palladium catalysts. Currently used palladium catalysts are reactive only with electron-rich arenes, unless an excess of arene is used, which limits synthetic applications. Here we report a 2-pyridone ligand that binds to palladium and accelerates non-directed C-H functionalization with arene as the limiting reagent. This protocol is compatible with a broad range of aromatic substrates and we demonstrate direct functionalization of advanced synthetic intermediates, drug molecules and natural products that cannot be used in excessive quantities. We also developed C-H olefination and carboxylation protocols, demonstrating the applicability of our methodology to other transformations. The site selectivity in these transformations is governed by a combination of steric and electronic effects, with the pyridone ligand enhancing the influence of sterics on the selectivity, thus providing complementary selectivity to directed C-H functionalization.

Bioactivity and structure-activity relationship of cinnamic acid esters and their derivatives as potential antifungal agents for plant protection

A series of cinnamic acid esters and their derivatives were synthesized and evaluated for antifungal activities in vitro against four plant pathogenic fungi by using the mycelium growth rate method. Structure-activity relationship was derived also. Almost all of the compounds showed some inhibition activity on each of the fungi at 0.5 mM. Eight compounds showed the higher average activity with average EC50 values of 17.4-28.6 μg/mL for the fungi than kresoxim-methyl, a commercial fungicide standard, and ten compounds were much more active than commercial fungicide standards carbendazim against P. grisea or kresoxim-methyl against both P. grisea and Valsa Mali. Compounds C1 and C2 showed the higher activity with average EC50 values of 17.4 and 18.5 μg/mL and great potential for development of new plant antifungal agents. The structure-activity relationship analysis showed that both the substitution pattern of the phenyl ring and the alkyl group in the alcohol moiety significantly influences the activity. There exists complexly comprehensive effect between the substituents on the phenyl ring and the alkyl group in the alcohol moiety on the activity. Thus, cinnamic acid esters showed great potential the development of new antifungal agents for plant protection due to high activity, natural compounds or natural compound framework, simple structure, easy preparation, low-cost and environmentally friendly.