96646-19-4

Upstream product

• 17942-96-0 3-(4-methoxyphenyl)-3-<(trimethylsilyl)oxy>propanoate d'ethyle 
• 24045-74-7 ethyl-2-chloro-3-(4-methoxyphenyl)-3-oxopropanoate 
• 123-11-5 4-methoxy-benzaldehyde 
• 105-36-2 ethyl bromoacetate 
• 141-78-6 ethyl acetate 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 64-17-5 ethanol 
• 22027-50-5 methyl 3-(4-methoxybenzoyl)acetate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 623-48-3 ethyl iodoacetae 
• 2881-83-6 ethyl 4-methoxybenzoylacetate 
• 105-39-5 chloroacetic acid ethyl ester 
• 42201-84-3 1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene 
• 123843-32-3 carbethoxymethyltri-n-butylstibonium tetraphenylborate 

Downstream Products

• 838841-72-8 butyric acid 2-ethoxycarbonyl-1-(4-methoxy-phenyl)-ethyl ester 
• 872428-03-0 (+/-)-3-hydroxy-N-methoxy-3-(4-methoxyphenyl)-N-methylpropanamide 
• 33172-00-8 ethyl (3S)-3-hydroxy-3-(4-methoxyphenyl)propanoate 
• 1449521-95-2 3-(tert-butyldimethylsilyloxy)-N-methoxy-3-(4-methoxyphenyl)-N-methylpropanamide 
• 1351766-81-8 3-ethoxy-1-(4-methoxyphenyl)-3-oxopropyl decanoate 
• 1351766-95-4 (S)-3-ethoxy-1-(4-methoxyphenyl)-3-oxopropyl decanoate 
• 1351766-65-8 (R)-3-ethoxy-1-(4-methoxyphenyl)-3-oxopropyl decanoate 
• 2881-83-6 ethyl 4-methoxybenzoylacetate 
• 31709-47-4 3-(4-methoxyphenyl)isoxazol-5(4H)-one 

Relevant academic research and scientific papers

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.

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.

Access to β-Hydroxyl Esters via Copper-Catalyzed Reformatsky Reaction of Ketones and Aldehydes

An efficient and simple Cu-catalyzed Reformatsky reaction of ketones and aldehydes has been accomplished with ethyl iodoacetate. Excellent yields of β-hydroxyl esters were achieved with a range of ketones and aldehydes, which varied from aromatic to aliphatic, unsaturated to saturated ketones and aldehydes. This practical and convenient transformation was conducted with inexpensive, readily available, and commercial starting materials under mild reaction conditions.

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.

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.

Bu 4 N + -Controlled Addition and Olefination with Ethyl 2-(Trimethylsilyl)acetate via Silicon Activation

Catalytic Bu 4 NOAc as silicon activator of ethyl 2-(trimethylsilyl)acetate, in THF, was utilized for the synthesis of β-hydroxy esters, whereas employing catalytic Bu 4 NOTMS gave α,β-unsaturated esters. The established reaction conditions were applicable to a diverse range of aromatic, heteroaromatic, aliphatic aldehydes and ketones. Reactions were achieved at room temperature without taking any of the specialized precautions that are in place for other organometallics. A stepwise olefination pathway via silylated β-hydroxy esters with subsequent elimination to form the α,β-unsaturated ester has been demonstrated. The key to selective product formation lies in use of the weaker acetate activator which suppresses subsequent elimination whereas stronger TMSO - activator (and base) facilitates both addition and elimination steps. The use of tetrabutyl ammonium salts for both acetate and trimethylsilyloxide activators provide enhanced silicon activation when compared to their inorganic cation counterparts.

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.

Evaluation of a new protocol for enzymatic dynamic kinetic resolution of 3-hydroxy-3-(aryl)propanoic acids

The application of tandem metal-enzyme dynamic kinetic resolution (DKR) is a powerful tool for the manufacture of high-value chemical commodities. A new protocol of kinetic resolution based on irreversible enzymatic esterification of carboxylic acids with orthoesters was introduced to obtain optically active β-hydroxy esters. This procedure was combined with metal catalyzed racemization of the target substrate providing both (R) and (S) enantiomers of ethyl 3-hydroxy-3-(4-nitrophenyl)propanoate with a high yield of 89% at 40°C. A substantial influence of the enzyme type, organic co-solvent, and metal catalyst on the conversion and enantioselectivity of the enzymatic dynamic kinetic resolution was noted.

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.