70200-12-3

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 141-78-6 ethyl acetate 
• 105-39-5 chloroacetic acid ethyl ester 
• 105-36-2 ethyl bromoacetate 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 64-17-5 ethanol 
• 63131-29-3 methyl 4-fluorobenzoyl acetate 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 1999-00-4 ethyl 3-(4'-fluorophenyl)-3-oxopropionate 
• 73250-02-9 3-(4-Fluoro-phenyl)-3-trimethylsilanyloxy-propionic acid ethyl ester 
• 623-48-3 ethyl iodoacetae 

Downstream Products

• 838841-75-1 butyric acid 2-ethoxycarbonyl-1-(4-fluoro-phenyl)-ethyl ester 
• 213201-62-8 1-(4-fluorophenyl)-1,3-propanediol 
• 31709-51-0 3-(4-fluorophenyl)isoxazol-5 (4H)-one 
• 1999-00-4 ethyl 3-(4'-fluorophenyl)-3-oxopropionate 
• 928780-19-2 4-amino-1-{3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-[4-(4-fluoro-phenyl)-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yloxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidin-2-one 

Relevant academic research and scientific papers

Synthesis method of beta-hydroxy ester compound

The invention belongs to the technical field of medicine and organic chemical synthesis, and discloses a synthesis method of a beta-hydroxy ester compound. An aldehyde compound and an iodo-acetate compound are used as raw materials; manganese powder is adopted as an accelerant, metal nickel salt is adopted as a catalyst and an organic solvent is adopted as a reaction medium, an organic protonic acid is added and stirred and reacted under inert gas protection, the reaction system is cooled to room temperature after the reaction is finished, vacuum distillation and concentration are performed toobtain a crude product, and column chromatography purification is performed to obtain the beta-hydroxy ester compound. The synthesis method is safe and simple to operate, raw materials are easy to obtain, the price is low, the reaction efficiency is high, and the yield can reach 90% or above and even reach 98%; the method is good in functional group adaptability, wide in substrate adaptability, environmentally friendly, beneficial to industrial production and wide in application in medicine and organic synthesis.

One-pot enol silane formation-Mukaiyama aldol reactions: Crossed aldehyde-aldehyde coupling, thioester substrates, and reactions in ester solvents

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and a trialkylamine base promote both in situ enol silane/silyl ketene acetal formation and Mukaiyama aldol addition reactions between a variety of reaction partners in a single reaction flask. Isolation of the required enol silane or silyl ketene acetal is not necessary. For example, crossed aldol reactions between α-disubstituted aldehydes and non-enolizable aldehydes yield β-hydroxy aldehydes in good yield. In a related reaction, the common laboratory solvent ethyl acetate functions as both an enolate precursor and a green reaction solvent. When thioesters are employed as enolate precursors, high yields for additions to non-enolizable aldehydes are routinely observed.

Iron(0)-Mediated Reformatsky Reaction for the Synthesis of β-Hydroxyl Carbonyl Compounds

An efficient, economical, and practical Reformatsky reaction of α-halo carbonyl compounds with aldehydes/ketones by using cheap and commercial iron(0) powder as reaction mediator is developed. The reactions proceeded effectively in the presence of a catalytic amount of iodine (20 mol %) to afford the synthetically useful β-hydroxyl carbonyl compounds in moderate to good yields.

A Ball-Milling-Enabled Reformatsky Reaction

An operationally simple one-jar one-step mechanochemical Reformatsky reaction using in situ generated organozinc intermediates under neat grinding conditions has been developed. Notable features of this reaction protocol are that it requires no solvent, no inert gases, and no pre-activation of the bulk zinc source. The developed process is demonstrated to have good substrate scope (39–82 % yield) and is effective irrespective of the initial morphology of the zinc source.

Method for preparing β - hydroxyl carbonyl compound (by machine translation)

The present invention relates to a process for preparing β - hydroxycarbonyl compounds, which mainly provides a process for the reaction, using inexpensive commercial iron powder-mediated α -halocarbonyl compounds with aldehydes/ketones, to provide the corresponding β - hydroxycarbonyl compound . the present invention relates to a method. The process is good, has wide functional group tolerance and good compatibility. (by machine translation)

Umpolung of protons from H2O: A metal-free chemoselective reduction of carbonyl compounds: Via B2pin2/H2O systems

H2O is routinely described as a proton donor, however, in the presence of diboron compounds, the umpolung reaction of H2O under metal-free conditions was successfully developed, which could afford hydride species, leading to a highly efficient and chemoselective reduction of CO bonds. This strategy exhibits excellent chemoselectivities toward carbonyl groups in the presence of ester, olefin, halogen, thioether, sulfonyl, cyano as well as heteroaromatic groups.

3-Arylpropionylhydroxamic acid derivatives as Helicobacter pylori urease inhibitors: Synthesis, molecular docking and biological evaluation

Helicobacter pylori urease is involved in several physiologic responses such as stomach and duodenal ulcers, adenocarcinomas and stomach lymphomas. Thus, inhibition of urease is taken for a good chance to treat H. pylori-caused infections, we have therefore focused our efforts on seeking novel urease inhibitors. Here, a series of arylpropionylhydroxamic acids were synthesized and evaluated for urease inhibition. Out of these compounds, 3-(2-benzyloxy-5-chlorophenyl)-3-hydroxypropionylhydroxamic acid (d24) was the most active inhibitor with IC50of 0.15?±?0.05?μM, showing a mixed inhibition with both competitive and uncompetitive aspects. Non-linear fitting of kinetic data gives kinetics parameters of 0.13 and 0.12?μg·mL?1for Kiand Ki′, respectively. The plasma protein binding assays suggested that d24 exhibited moderate binding to human and rabbit plasma proteins.

Synthesis, molecular docking and kinetic properties of β-hydroxy- β-phenylpropionyl-hydroxamic acids as Helicobacter pylori urease inhibitors

Inhibition of urease results in Helicobacter pylori growth arrest in the stomach, promoting urease as promising targets for gastrointestinal ulcer therapy. Twenty hybrid derivatives of flavonoid scaffold and hydroxamic acid, β-hydroxy-β-phenylpropionylhydroxamic acids, were therefore synthesized and evaluated against H. pylori urease. Biological evaluation of these compounds showed improved urease inhibition exhibiting micromolar to mid-nanomolar IC50 values. Most importantly, 3-(3-chlorophenyl)-3- hydroxypropionyl-hydroxamic acid (6g) exhibited high potency with IC 50 of 0.083 ± 0.004 μM and Ki of 0.014 ± 0.003 μM, indicating that 6g is an excellent candidate to develop novel antiulcer agent. A mixture of competitive and uncompetitive mechanism was putatively proposed to understand the inconsistency between the crystallographic and kinetic studies for the first time, which is supported by our molecular docking studies.

Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: The influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications

Two series (para- and meta-substituted) of racemic methyl esters of 3-aryl-3-hydroxypropionic acid were prepared after which the enantiomers were separated by an enzyme-catalyzed transesterification. Several lipases were investigated as the catalyst. The influence of the enzyme pretreatment, as well as substrate concentration, reaction temperature, stirring manner, and substrate conversion on the stereochemical outcome of the biotransformation process were investigated in detail. The best results were achieved by using solvent-pretreated lipase from Pseudomonas fluorescens or Burkholderia cepacia suspended in toluene, and vinyl acetate as the acetyl group donor.

N-heterocyclic carbene mediated Reformatsky reaction of aldehydes with a-trimethylsilylcarbonyl compounds

N-Heterocyclic carbenes have been employed as highly efficient organocatalysts to mediate silyl-Reformatsky type reaction. In the presence of only 0.5 mol % nucleophilic carbene 1, various aldehydes coupled with α-trimethylsilylethylacetate very smoothly in DMF at room temperature to provide the corresponding β-hydroxyesters in moderate to high yields. α-Trimethylsilylketone and α-trimethylsilylamide can also undergo the addition reaction to give β-hydroxyketone and b-hydroxyamide in moderate yields.