70200-16-7

Upstream product

• 141-78-6 ethyl acetate 
• 1122-91-4 4-bromo-benzaldehyde 
• 623-48-3 ethyl iodoacetae 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 73250-08-5 3-(4-Bromo-phenyl)-3-trimethylsilanyloxy-propionic acid ethyl ester 
• 5764-82-9 bromo(2-ethoxy-2-oxoethyl)zinc 
• 99-90-1 para-bromoacetophenone 
• 64-17-5 ethanol 
• 126629-81-0 methyl 3-(4-bromophenyl)-3-oxopropanoate 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 223552-78-1 3-(4-bromophenyl)-3-fluoropropyl acetate 
• 910135-67-0 C₁₆H₁₆BrN₃O₂S 
• 928780-48-7 4-{2-[5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethoxy]-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-4-yl}-benzoic acid methyl ester 
• 928780-21-6 4-amino-1-[5-[4-(4-bromo-phenyl)-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yloxymethyl]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1H-pyrimidin-2-one 
• 862187-65-3 4-(1,3-dihydroxypropyl)benzoic acid methyl ester 
• 219745-18-3 1-(4-bromophenyl)-1,3-propanediol 
• 910135-62-5 3-(4-bromo-phenyl)-3-hydroxy-propionic acid hydrazide 

Relevant academic research and scientific papers

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.

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)

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.

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.

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.

A rapid and diverse construction of 6-substituted-5,6-dihydro-4-hydroxy-2- pyrones through double Reformatsky reaction

A rapid and diverse synthesis of biologically important 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through a double Reformatsky reaction of aldehydes to δ-hydroxy-β-ketoesters followed by lactonization is described. Due to the high functional group tolerance and reaction site discrimination between aldehyde, nitrile, and ester groups in the substrate, the protocol can provide the dihydropyrones with bromo, nitro, carboxylic acid, and β-ketoester groups, which are suitable for the further derivatizations. Furthermore, the protocol has been successfully applied to the rapid total synthesis of naturally occurring Yangonin.

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.

P(i-PrNCH2CH2)3N: Efficient catalyst for synthesizing β-hydroxyesters and α,β-unsaturated esters using α-trimethylsilylethylacetate (TMSEA)

(Chemical Equation Presented) We present an efficient synthesis of β-hydroxyesters and R,β-unsaturated esters via activation of the silicon-carbon bond of α-trimethylsilylethylacetate using catalytic amounts of the commercially available P(i-PrNCH2CH2) 3N 1a. Selectivity for either of these two products can be achieved simply by altering the catalyst loading and reaction temperature to afford addition or stereoselective condensation. This method is mild and tolerates a wide array of functional groups.

Dimethylzinc-mediated, oxidatively promoted Reformatsky reaction of ethyl iodoacetate with aldehydes and ketones

A practical and general Reformatsky reaction, promoted by oxidants and mediated by dimethylzinc, is described. The reaction is fast and runs at 0°C with aldehydes and ketones, under mild reaction conditions. Preliminary results obtained for the enantioselective version show that inexpensive chiral amino alcohols could be used in the challenging formation of enantioenriched quaternary stereogenic centers.