3306-05-6

Upstream product

• 463-51-4 Ketene 
• 7568-93-6 2-Amino-1-phenylethanol 
• 75-36-5 acetyl chloride 
• 1846-33-9 N-phenacylacetamide 
• 64-19-7 acetic acid 
• 62-53-3 aniline 
• 108-22-5 Isopropenyl acetate 
• 100-42-5 styrene 
• 1499-00-9 2-phenylaziridine 
• 96-09-3 styrene oxide 
• 75-05-8 acetonitrile 
• 507-09-5 tiolacetic acid 
• 5468-37-1 2-aminoacetophenone hydrochloride 
• 37394-53-9 ω-aminoacetophenone hydrobromide 

Downstream Products

• 1721-93-3 1-methylisoquinoline 
• 149342-38-1 2-acetamido-1-phenylethyl acetate 
• 1846-33-9 N-phenacylacetamide 
• 149342-37-0 (R)-N-(2-hydroxy-2-phenylethyl)acetamide 
• 51626-52-9 N-(2-(1H-indol-3-yl)-2-phenylethyl)acetamide 
• 2549-14-6 (R)-2-Amino-1-phenylethanol 
• 56613-81-1 (S)-2-Amino-1-phenyl-1-ethanol 
• 3433-15-6 rac-5-phenyl-1,3-oxazolidine-2-thione 
• 7693-77-8 5-phenyloxazolidin-2-one 
• 7007-19-4 N-benzoyl-5-phenyl-oxazolidin-2-one 
• 109355-73-9 ethyl 2-hydroxy-2-phenylethylcarbamate 
• 7568-93-6 2-Amino-1-phenylethanol 

Relevant academic research and scientific papers

Easy kinetic resolution of some β-amino alcohols by Candida antarctica lipase B catalyzed hydrolysis in organic media

Herein, we present an easy and eco-friendly pathway to obtain some enantiomerically enriched β-amino alcohols using essentially as β-blockers. The enzymatic hydrolysis is conducted in hydrophobic organic media, assisted by sodium carbonate and CAL-B. We describe a new and effective procedure in terms of the chemo- and enantioselectivity, which allows for the formation of both enantiomers: the 2-acetamido-1-arylacetates and 2-acetamido-1-arylethanols were obtained with high ee values (up to >99%), while the selectivities reached E >200. The obtained results show a high CAL-B affinity toward the deacylation of the 2-acetamido-1-arylacetates compared to the acylation one. The structure of the 2-acetamido-1-arylacetates had a significant influence on both reactivity and selectivity of the CAL-B catalyzed deacylation. A multigram scale O-deacylation of racemic 2-acetamido-1-phenylacetate has been carried out, giving access both enantiomers with high enantiomeric purity and good isolated chemical yields.

Direct catalytic synthesis of unprotected 2-amino-1-phenylethanols from alkenes by using iron(II) phthalocyanine

Aryl-substituted amino alcohols are privileged scaffolds in medicinal chemistry and natural products. Herein, we report that an exceptionally simple and inexpensive FeII complex efficiently catalyzes the direct transformation of simple alkenes into unprotected amino alcohols in good yield and perfect regioselectivity. This new catalytic method was applied in the expedient synthesis of bioactive molecules and could be extended to aminoetherification.

Green synthesis of benzamides in solvent- and activation-free conditions

Herein, we describe a clean and ecocompatible pathway for both N-benzoylation and N-acetylation of anilines, amines, diamines, and aminoalcohols using three enol esters with good yields. We have improved the use of vinyl benzoate for the direct introduction of a benzamido-moiety under solvent- and activation-free conditions. The recovered amides are easily isolated by crystallization. Copyright

Steric vs. electronic effects in the Lactobacillus brevis ADH-catalyzed bioreduction of ketones

Lactobacillus brevis ADH (LBADH) is an alcohol dehydrogenase that is commonly employed to reduce alkyl or aryl ketones usually bearing a methyl, an ethyl or a chloromethyl as a small ketone substituent to the corresponding (R)-alcohols. Herein we have tested a series of 24 acetophenone derivatives differing in their size and electronic properties for their reduction employing LBADH. After plotting the relative activity against the measured substrate volumes we observed that apart from the substrate size other effects must be responsible for the activity obtained. Compared to acetophenone (100% relative activity), other small substrates such as propiophenone, α,α, α-trifluoroacetophenone, α-hydroxyacetophenone, and benzoylacetonitrile had relative activities lower than 30%, while medium-sized ketones such as α-bromo-, α,α-dichloro-, and α,α-dibromoacetophenone presented relative activities between 70% and 550%. Moreover, the comparison between the enzymatic activity and the obtained final conversions using an excess or just 2.5 equiv. of the hydrogen donor 2-propanol, denoted again deviations between them. These data supported that these hydrogen transfer (HT) transformations are mainly thermodynamically controlled. For instance, bulky α-halogenated derivatives could be quantitatively reduced by LBADH even employing 2.5 equiv. of 2-propanol independently of their kinetic values. Finally, we found good correlations between the IR absorption band of the carbonyl groups and the degrees of conversion obtained in these HT processes, making this simple method a convenient tool to predict the success of these transformations. The Royal Society of Chemistry.

Synthesis of new N-acryl-1-amino-2-phenylethanol and N-acyl-1-amino-3- aryloxypropanols and evaluation of their antihyperlipidemic, LDL-oxidation and antioxidant activity

As a part of our drug discovery program, we identified an alkaloidal amide i.e. Aegeline (V) isolated from the leaves of Aegle marmelos as a dual acting agent (antihyperlipidemic and antihyperglycemic). In continuation of this program, we synthesized new N-acyl-1-amino-2-alcohols (N-acrylated-1-amino-2- phenylethanol and N-acylated-1-amino-3-aryloxypropanols) via Ritter reaction and screened for their in-vivo antihyperlipdemic activity in Triton induced hyperlipidemia model, LDL-oxidation and antioxidant activity. Compounds 3, 11 and 13 showed good antihyperlipidemic activity, LDL-oxidation as well as antioxidant activity and comparable activity with marketed antidyslipidemic drug.

Thioacids mediated selective and mild N-acylation of amines

N-Acylated amines are ubiquitous in nature. Selective N-acylation at neutral conditions remains a key area of interest. Here we are reporting the copper sulfate-mediated highly selective, mild, and rapid N-acylation of various aliphatic and aromatic amines using thioacids in methanol at neutral conditions. All N-acylated products of primary and secondary amines were isolated in good to excellent yields. This method is found to be highly selective for the amines and not sensitive to other functional groups such as phenols, alcohols, and thiols. The simple workup, high yields, and high selectivity of this reaction can be an attractive alternative to those of the existing acyl halide- and acid anhydride-mediated N-acylation reactions.

Isopropenyl acetate, a remarkable, cheap and acylating agent of amines under solvent- and catalyst-free conditions: A systematic investigation

Isopropenyl acetate was proved to be an efficient reagent for acetylation of amine in the absence of solvent and catalyst. The corresponding acetamides were obtained in very high yields without any purification.

Synthesis of novel trisubstituted imidazolines

Imidazolines substituted at the 1- and either the 4-, or 5-position with phenyl and at the 2-position with alkyl or phenyl have been prepared in racemic form. They appear to be fairly stable compounds and potentially useful as scaffolds in medicinal chemistry. Georg Thieme Verlag Stuttgart.

Convenient, cost-effective, and mild method for the N-acetylation of anilines and secondary amines

An efficient, cost-effective, and mild method for the N-acetylation of anilines and secondary amines with ammonium acetate in acetic acid media at reflux temperature in good yield is described. Copyright Taylor & Francis, Inc.

Thermolytic Carbonates for Potential 5′-Hydroxyl Protection of Deoxyribonucleosides

Thermolytic groups structurally related to well-studied heat-sensitive phosphate/thiophosphate protecting groups have been evaluated for 5′-hydroxyl protection of deoxyribonucleosides as carbonates and for potential use in solid-phase oligonucleotide synthesis. The spatial arrangement of selected functional groups forming an asymmetric nucleosidic 5′-O-carbonic acid ester has been designed to enable heat-induced cyclodecarbonation reactions, which would result in the release of carbon dioxide and the generation of a nucleosidic 5′-hydroxyl group. The nucleosidic 5′-O-carbonates 3-8, 10-15, and 19-21 were prepared and were isolated in yields ranging from 45 to 83%. Thermolytic deprotection of these carbonates is preferably performed in aqueous organic solvent at 90 °C under near neutral conditions. The rates of carbonate deprotection are dependent on the nucleophilicity of the functional group involved in the postulated cyclodecarbonation reaction and on solvent polarity. Deprotection kinetics increase according to the following order: 4 5 10 6 12 7 13 8 14 ? 19-21 and CC14 dioxane MeCN t-BuOH MeCN:phosphate buffer (3:1 v/v, pH 7.0) EtOH:phosphate buffer (1:1 v/v, pH 7.0). Complete thermolytic deprotection of carbonates 7, 8, 13, and 14 is achieved within 20 min to 2 h under optimal conditions in phosphate buffer-MeCN. The 2-(2-pyridyl)amino-1-phenylethyl and 2-[N-methyl-N-(2-pyridyl)]aminoethyl groups are particularly promising for 5′-hydroxyl protection of deoxyribonucleosides as thermolytic carbonates.