51699-39-9

Upstream product

• 631-61-8 ammonium acetate 
• 27834-99-7 ethyl (3-methoxybenzoyl)acetate 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 591-31-1 3-methoxy-benzaldehyde 
• 64-17-5 ethanol 
• 779-81-7 methyl 3-(3-methoxyphenyl)-3-oxopropanoate 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 141-78-6 ethyl acetate 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 51699-44-6 1-(3-methoxyphenyl)propane-1,3-diol 
• 72913-59-8 5-methoxy-2-inden-1-one 
• 123208-90-2 endo-1,2-(4'-(tert-butyldimethylsilyl)benzo)-5,6,6-triphenylbicyclo<3.1.0>hex-5-yl acetate 
• 123208-89-9 endo-1,2-(4'-(tertbutyldimethylsilyl)benzo)-5,6,6-triphenylbicyclo<3.1.0>hexan-5-ol 
• 123208-88-8 endo-1,2-(4'-hydroxybenzo)-5,6,6-triphenylbicyclo<3.1.0>hexan-5-ol 
• 123208-82-2 7,9,9-triphenyltricyclo<4.4.0.0>-deca-1,4,6-trien-3-one 
• 123208-80-0 5,7,8-triphenyl-2-naphtol 
• 123208-86-6 1,2-(4'-methoxybenzo)-6,6-diphenylbicyclo<3.1.0>hexan-3-one 
• 123208-87-7 1,2-(4'-hydroxybenzo)-6,6-diphenyl<3.1.0>hexan-5-one 
• 123208-85-5 β-(3-methoxyphenyl)-β-hydroxypropionic acid 

Relevant academic research and scientific papers

A facile one-pot synthesis of chiral β-amino esters

We report a facile one-pot synthesis of chiral β-amino esters via direct reductive amination of β-keto esters with ammonium acetate (NH 4OAc) and H2 in the presence of chiral Ru-ClMeOBIPHEP catalysts using 2,2,2-trifluoroethanol (TFE

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.

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.

A prodrug approach towards the development of tricyclic-based FBPase inhibitors

For the purpose of reducing the strong CYP3A4 inhibitory potency of diamide prodrug 4, cyclic prodrugs of tricyclic-based FBPase inhibitors were synthesized. Extensive SAR studies led to the discovery of pyridine-containing cyclic prodrug 20, which strong

A simple and efficient procedure of low valent iron- or copper-mediated reformatsky reaction of aldehydes

(Chemical Equation Presented) An operationally simple and very efficient procedure of Reformatsky reaction of aldehydes has been carried out in THF in the presence of low valent iron or copper which were prepared in situ employing a bimetal redox strategy through reduction of FeCl3 or CuCl 2-2H2O with magnesium.

Photochemistry of Some Extended ?-Systems: Type A and Aryl Rearrangements of Systems with Extended Conjugation Related to Cyclohexadienones and Cyclohexenones. Mechanistic and Exploratory Organic Photochemystry

6,6-Diphenyl-2(6H)-naphthalenone and 5,6,6-triphenyl-2(6H)-naphthalenone were sinthesized as extended relatives of 4,4-diphenylcyclohexadienone and their photochemistry was investigated.In the case of the diphenylnaphthalenone, irradition resulted in a regioselective phenyl migration and formation of 5,6-diphenyl-2-naphthol whether the photolysis was in methanol or in benzene.Irradiation of the triphenylnaphthalenone in methanol or isopropyl alcohol afforded a product in which one molecule of solvent and one molecule of molecular oxygen were incorporated.Photolysis in acetonitrile led instead to a tricyclic photoproduct in a process reminiscent of the type A rearrangement of 2,5-cyclohexadienones.This tricyclic photoproduct itself was photochemically reactive and rearranged regioselectively to afford 5,7,8-triphenyl-2-naphthol.By trapping, a tricyclic zwitterion was shown to play a role in the rearrangement of the triphenylnaphthalenone.The photochemystry of both naphthalenones was shown by quenching to result from triplet excited states.Lack of reactivity on sensitization suggested the photochemystry derives from Tn.The quantum efficiencies were shown to be lower and the triplet reaction rate slower in the comparison with the monocyclic 4,4-diphenylcyclohexadienone.Finally, enone analogues were investigated.Both 6,6-diphenyl-4,4a,5,6-tetrahydro-2(3H)-naphthalenone and 6,6-diphenyl-4,4a,5,6,10,10a-hexahydro-2(3H)-anthracenone were synthesized.Only the former was reactive; phenyl migration resulted in formation of four stereoisomeric tricyclic ketones whose structures were established by X-ray analysis.For all of the various reactions, mechanisms are provided and discusseed along with MNDO-CI computations.